Chapter 1: Girl Gone Wild
Chapter Text
Morning broke soft and golden over Madison Avenue, spilling honeyed light through the long rose-pink curtains at your window and the linen canopy draped around your bed. It shimmered across the carpet, pooled over the cashmere throw, and kissed your bare shoulder with a warmth so gentle it almost convinced you the pounding in your head was just a dream. You began to surface from sleep like rising through champagne: light headed, sticky, and dizzy. You’re not sure what stirred you awake, only that the scent of last night still clung to you, to the room, to your silk sheets tangled around your legs. You breathed in the smell of jasmine and top shelf vodka as you rolled over and faced the sunshine.
You’re grateful, really, that somehow you ended up back home safe and sound. Last night was such a blur you only barely recalled stripping your clothes off the second you walked in, leaving yourself bare beneath the down comforter and silken white sheets. Curled up in your lavish bed, your eyes too heavy and your mouth vaguely tasted like chocolate and alcohol. It wasn’t any surprise. You were well known for raiding the cabinet for something sweet on any given occasion, really. And a night out for drinks was no different.
The light pouring in from the windows and across the bed hurt. Your feet hurt. And God, your head hurt. On the floor, your clothing lay at odd angles, dress draped haphazardly over your pink velvet vanity chair and strappy heels abandoned at the door. Your hand dragged down your face, coming up messy with mascara and smudged foundation, your hair a tangled rat’s nest stuck to your cheek, sticky with lip gloss.
Your phone buzzed on the nightstand; you vaguely remembered it doing the same just moments ago, likely what had woken you.
You groaned, turning over to the side of your bed until your fingers slapped on the wood, blindly reaching for the device. As your fingers wrapped around it, you squinted at the brightness when you pulled it into your face. The screen was already crowded with texts and notifications, all of them pinging like little grenades across your vision.
You didn’t even bother clicking the photo from Gossip girl. You already had an awful, awful feeling sinking in your stomach to accompany the nausea. Memories of camera flashes blinding your vision, the crisp night air against your hot skin and stumbling into the car at the end of the night blurred in your mind. You’re almost certain you cursed out the paparazzi as you left too.
More texts came in, more DMs from strangers and someone you swore you’d blocked last week. You sent a welfare check to Blair, letting her know you were safely in bed. Sighing, you looked through the rest of your notifications, thumb frozen above the screen before you decided to throw the phone across the room. It smacked against the glossy pile of Vogue magazines on your desk, sending them falling to the floor until silence folded back over you. Pressing the heels of your hands into your eyes, you flopped onto your back, staring at the colors bursting behind your eyes.
Eventually, you knew you’d have to face the world. So you headed for the en suite, shuffling your bare feet across the soft carpet until your toes hit the cold marble. Your head pulsed behind your eyes, body moving heavy as stone as you faced the wreckage in the mirror. You winced at the vision of yourself: tangled hair sticking to your face and black mascara circles beneath your eyes. You looked like you’d slept through world war three.
You began assessing the rest of the damage, pulling a comb through the tangled mess of your hair, brushing your teeth three times and still tasting remnants of the vodka sodas you’d consumed. You wiped away the makeup with a damp cloth that smelled like rosewater, taking your time and dragging yourself through the routine, hoping maybe the longer you lingered, the easier it would be to enjoy the quiet before the storm.
With a fresh satin lounge set on and looking as presentable as you could hope to be in your state, you made your way downstairs, fingers gripping the polished mahogany banister for support. The morning light flooded the room through floor-to-ceiling windows even through the sheer silk curtains. It struck the marble floor, creamy white and veined in golds and gray, the kind of blinding light that made the back of your eyes throb against it.
The dining table came into view and was set for breakfast, a gleaming pitcher of orange juice and kettle of coffee calling your name. Even on a Saturday morning it was fit for a front page of Architectural Digest. A long, lacquered table stretched beneath a low hanging crystal chandelier, the place settings already neatly arranged with heavy silver flatware that caught the light like mirrors. A Baccarat pitcher of fresh orange juice beading gently with condensation sat beside a matching carafe of black coffee, both calling your name.
You squinted slightly against the brightness reflecting off the stone floor, adjusting to the light. Your mother was already seated, picture-perfect in her usual place, a china teacup delicately poised between her fingers, her lips painted the exact shade of peony pink that matched the fresh arrangement at the center of the table.
You slid into the chair across from her. She didn’t speak, just turned a page of the Financial Times with quiet practiced precision, her expression unreadable.
“Morning, Mom,” you grumbled, reaching for the juice. But before she could respond, another voice cut through the room—low, baritone, and unmistakably commanding in its presence.
“And how was your night, young lady?” your father asked as he sat to your right at the head of the table.
His face was freshly shaven, the blue suit pressed to perfection, tie knotted snug at his throat. Every inch of it tailored within a millimeter of precision. His salt-and-pepper hair was slicked back with gel even on a Saturday morning. He looked like he was on his way to a board meeting, not sitting down to breakfast with his hungover daughter.
“Fine.” you mumbled, sipping the juice in the hopes it would quench your suddenly dry throat.
“Indeed,” he said. He reached for the coffee, poured himself a cup, added just a touch of cream, everything meticulous as always. He stirred slowly, the spoon tapping against the porcelain like a clock ticking down.
He took a slow sip, and you realized he hadn’t even looked at you once this entire time.
Setting down his mug with a soft clink, he pulled out something from his jacket, “Sure seems like you had fun.”
The sudden slap of the tabloid section of the morning paper hit the spotless glass table sharp and final, the sound making your already throbbing head pulse harder and a fresh wave of nausea creep up your throat.
Your father leaned forward, fingers steepled as his elbows rested, his fingers pressing into his lips as if to hold back the true wrath behind his lips. His voice was controlled and low when he finally spoke.
“Imagine waking up this morning, reaching for the paper to catch up on the weekend markets, maybe check my emails before my first call, and instead finding this.” He dropped his hand, forefinger pointing hard into the black and white photo at the headline.
You dared a glance at the paper, and there you were. Mid-laugh, eyes glassy, the car window rolled halfway down. Your smile was wide and your hands were caught in motion, lifting the hem of your blouse up to your clavicle. Right beneath it, the photo was censored, two blurred circles stamped across your bare chest. You winced, heat flooding your cheeks, shame blooming fast and sick in your stomach.
“My own daughter—shirt off, flashing the damn paparazzi on a night out.” His voice was low and precise, a man delivering a verdict. “What in the world were you thinking?”
You slumped deeper into your chair, the cool leather sticking to your bare thighs. Your palms, clammy with guilt and hangover sweat, came up to shield your eyes.
Your mother exhaled a high, theatrical sigh as she set down her mug across from you.
“Look at me when I’m speaking to you, young lady.” your father commanded.
You dragged your hands down your reddening face, turning towards him with a pout. Everything about him looked freshly pressed, polished, and perfect. He looked so severe as he glared at you—the picture of legacy and discipline, like you were supposed to be.
“I’m sorry,” you whispered, voice wavering.
He was watching you when your eyes met his, his anger sliding into disappointment, something like sadness in his eyes.
“I’m sure you are, pumpkin.” he said, the heart of his palm swiping across his face, “But don’t think you can wipe this clean with some half-assed apology.” he tapped a stern finger on the tabloid again. The photo bended under his sharp pointed digit.
“What do you want me to say?” you said, voice thick, “I had too much to drink, I was stupid. It won’t happen again, daddy. I’m sorry.”
Your mother let out another sharp tut, but your father kept going.
“Something needs to change. You’re not a teenager running around Ibiza anymore. You’re the face of this family’s future, whether you like it or not. You think this is what I worked my whole life for? That I built our name so my daughter could be treated as a punchline? You think those diamonds in your ears, your Hermes bags, your Amex black card all pay for themselves?”
You had half a heart to tell him your brother actually was the one who was the face of the family name, but you didn’t think you could stomach the look that would cross his face. So instead, you shook your head, shameful, “I’m sorry, Daddy.”
“Good. Because starting now, it’s over.”
Your heart dropped to your stomach, and you sat bolt upright in your seat, “Wait–what? No, Daddy, no, Blair and I are flying to Greece this weekend! We have the yacht ready, the hotel in Santorini—everything’s already planned, I can’t just cancel.”
“You can,” your mother finally said, voice sharp and throwing her napkin down after dabbing the corners of her mouth, “And you will. Enough of this. Enough crying your way out of trouble. You're in your twenties, for god sake! This isn’t some harmless mistake, you acted like a downtown slut and got plastered across the front page.” she waved her hand in the air, “You can forget about your cover with Forbes. Vogue sure isn’t going to take you back after this little stunt…you can forget it all. This is a disgrace.”
Her voice was so crisp and cruel, her tea cold and forgotten at her elbow and her fury taking up every inch of space in the room. She sat stiffly at the table in a bright Lululemon set that looked untouched by actual exercise, posture perfect.
You watched her, feeling so unbearably small under her eyes, and turned back to your father, “Daddy, please—”
“Your mother is right,” he cut in. There wasn’t even anger in his voice, just something worse like resolve.
You pressed both hands over your eyes again, “Just…just tell me what I can do. To make it right.”
Your voice cracked around the words, all your plans for beachside Aperol Spritzes disintegrating into nothing. You could practically feel the sea breeze slipping through your fingers with it.
He leaned forward, and you watched him through split fingers, his elbows on the glass like a man making a deal, “Here is what’s going to happen. I’m giving you two months. Eight weeks without your credit cards, without store allowances. I want you to get yourself together. Maybe find a job, your own apartment, I don’t know. Something useful, something that puts your head back on your shoulders. Prove to me you can handle yourself, that you can be something other than this.”
“And maybe a nice man to settle you down,” your mother chimed in, suddenly calmer. “That’s what you need. I can call up the girls from tennis. They all have sons. Trust fund babies around your age and handsome, polished—”
“God, no,” you snapped through your tears. “I don’t want any of those preppy assholes.”
“Enough,” your father said, voice cutting clean across the room. “Finding someone respectable isn’t a punishment. It’s a step in the right direction. A partner keeps you grounded. Gives people less reason to talk. And frankly, right now, anything that helps the press take you seriously again is worth considering.”
“I’m not some PR campaign, Dad,” you muttered. “And I’m not going to date someone just to make you look better.”
He ignored you, “You get eight weeks. That’s the offer. Find some stability, and maybe someone who brings out the version of you I used to be proud of. Do that, and I’ll restore your accounts. If you don’t…”
You swallowed hard, wiping your eyes.
“...if I don’t?”
He shrugged, already standing. “Then you’re cut off. You’ll turn in your cards, your keys. You’ll find a new apartment on your own dime. And you’ll learn the hard way just how far your name alone gets you.”
The polished wood table sat between you like a mirror, reflecting everything you were about to lose.
“Okay,” you whispered, throat thick and tight.
He paused, adjusting the cuff of his suit like the conversation hadn’t hollowed you out. His tone softened slightly, not warm but almost… performative.
“I love you, honey. This is for your own good.”
That night, you nursed your gin martini at the hotel bar like it was medicine. It was the kind that didn’t fix anything but at least made you forget it for a few hours. The ice-cold glass sat heavy in your hand, the drink perfectly dirty, just how you liked it—briny and bitter. You chuckled, thinking that’s exactly how you felt too.
When you’d finally had the nerve to leave the house and walk down the street to the Rosewood Hotel, you’d made yourself at home at the bar as the rest of the city lived their lives behind you.
You’d tipped the bartender a handful of cash to keep the martinis comin’, using the emergency stash that had been stuffed into your closet drawer since Christmas, courtesy of your grandmother.
Buy something nice, or get that nose fixed, whichever comes first, she’d told you, as she'd handed you the envelope. A nose job would do numbers, honey. It’s only a couple weeks of rest, anyway.
You’d laughed her off, taking the money and stashing it for emergencies like this.
And now, sitting at Belmans Bar inside the hotel on the Upper East side in your red bottomed heels and all black attire, you half heartedly stirred your drink, hoping to God the bartender didn’t recognize you.
Your phone sat facedown for a while, but eventually, boredom and self pity rang louder than your pride and you picked it up and started to scroll.
Your own downfall was everywhere. Flashbulb-lit screenshots from the afterparty, that blurred-out photo of your chest from the curbside car door, a thousand IG stories captioned with your name, half of them mocking, the other half pretending to be concerned.
As you scrolled, you finally got a small relief of a post that wasn’t your blurred out tits and a headline. But this photo looked different. It was grainier, taken from behind a car tinted window late at night. A teenage girl, maybe fifteen, ducking into a black car with a hand covering her face. She looked…miserable.
CASTILLO DAUGHTER ESCORTED INTO REHAB FACILITY?
Yeesh, at least you weren’t that bad.
As you looked closer, you recognized her. Of course you did. Everyone knew the Castillo name. Your families had circled each other for years—same charity galas, same tax bracket, same stuffy luncheons celebrating some Ivy League degree or another. There’d never really been anyone your age in their family to talk to, just polite nods and mutual attendance at mutual obligations. Wedding season, debutante balls, the usual revolving door of the one percent’s social calendar.
You only kind of knew Camilla. She was younger, sweeter, and much more tame. She was the daughter of Peter and Charlotte Castillo. Always so prim and proper, she was so put together in her ballet flats and perfect posture anytime you saw her. She was the kind of daughter your parents always wished you were. And now, looking so disheveled, rushing into an unmarked SUV, it made your stomach twist, wincing at the thought. She looked how you felt lately.
The internet was still feasting on her photo as you scrolled, headlines dissecting her sad face, the slump of her shoulders, her broken frame as if it were sport.
Eventually, you couldn’t take it anymore. You switched to Raya, hoping to find something—someone—that might appease your father’s expectations. You swiped through an endless parade of polo-wearing trust fund boys you already knew too well. Every face was another recycled name from childhood birthdays, graduation parties, foundation dinners. Hell really did have its own social calendar.
Then came the celebrities. Too recognizable, too chaotic. All of them too coked out or too committed to their own image to be of any use to your father. Some you’d met, a few you’d kissed, most you knew well enough to stay far, far away from.
As the bartender set down your third martini, you plucked the olive from the glass, chewing slowly. You held the pick between your lips like a cigarette, scrolling with your free hand. And just as you were thinking to gulp down your entire glass and head home, someone slid into the stool beside you.
You heard a low exhale as they fell into the seat, a quiet, polite ordering of tequila on ice. You glanced sideways as the man slid his hand down from his mouth to the nicely trimmed dark mustache and five o clock shadow around his chin and jaw. An emerald green ring gleamed at you, encased in gold on his opposite ring finger.
“Harry,” you muttered in greeting, flitting your gaze between him and back to your phone.
His head turned, molasses brown eyes blinking once before recognition settled in, “Oh,” he said, sitting up a little straighter, “Sorry, I didn’t realize it was you.”
“Oh, it’s me alright,” you said, voice flat as you scrolled. You didn’t stop swiping, just leaned your elbow on the bar, screen casting soft light across your face.
Harry’s drink arrived. He took a sip, slow and steady, and you could feel his eyes watching you over the rim of the glass, then landing on the half empty one in your hand. “And… How many martinis in are you?”
“Don’t judge me,” you quip back. “You came here to drink alone too.”
“I’m not judging,” he said, gesturing lazily with the glass. “Just…making sure you’re…” he couldn’t seem to find the words before finally settling on, “well, especially after the last twenty-four hours…”
You paused mid-swipe and looked at him with a raised brow. “Are you referring to my tits on the cover of TMZ this morning, Mr. Castillo?”
He smirked, eyes flicking back to his drink. “I guess I am.”
“Charming.”
He huffed a little laugh, “But really, are you alright?”
You scoffed back, “Define alright.”
“I mean… not spiraling publicly would be a start.”
“Oh, well, then no. Not alright at all.”
There was a beat of quiet between you, the kind that wasn’t uncomfortable but wasn’t quite easy either. Just... stale, and a little heavy. You let your gaze move over him—pristine even now, dressed in a navy cashmere sweater that looked simple but intentional, sleeves pushed just high enough to show his silver Rolex. His dark wash jeans were the kind you knew cost more than most people’s rent, and the emerald ring on his right hand caught the light again as he turned his glass between his fingers.
“Didn’t think this was your scene,” you said finally.
“Well, the hotel belongs to my family,” he replied. “I’m here more often than I’d like to admit.”
You bit your lip, setting down your glass, “Right…sorry.”
He sighed again, deep and long as he took another sip of tequila, “Besides…they’re all here. Upstairs in the Penthouse for the night.”
“Why?”
“We had a, uh... ‘family meeting.’”
There was something surprisingly genuine in the way he said it, though it was obvious he was exhausted by it. Harry always had that about him even when he was guarded, when he dressed everything in civility and charm. There was a softness there, something unpolished beneath all the carefully crafted exterior.
“A family meeting?” you asked, finally setting your phone down and turning toward him.
He gave a short nod. “You’re not the only one in the news lately, if you hadn’t noticed.”
Oh.
“Camilla,” you breathed, stomach sinking, “Is she okay?”
Harry didn’t answer right away. His fingers turned his glass slowly, his gaze fixed on the clear liquid inside like he might find something helpful there. When he did look up, his eyes were as big and brown and heartbreakingly kind—eyes that seemed too soft, too honest to belong in your world of trust funds and galas.
“I don’t really know,” he said quietly. “She’s just… going through something.”
“Okay...”
“She’s struggling,” he sighed, a faint roughness at the edge of his voice. “I don’t fully understand it, but I know it’s real. My brother, her own father, refuses to see it that way. Thinks it’s for attention, which I find frankly infuriating. So we had a meeting after everything that happened last night. Everyone is just scared, so they sent her off to that rehabilitation center.”
You blinked, then shook your head. Harry didn’t seem interested in giving you all the details—and honestly, you knew he didn’t owe you any. The two of you barely knew each other outside of events and obligatory paths being crossed. Whatever happened, it was family business, and it wasn’t your place to pry. But still, before you could think better of it, your hand reached out and came to rest gently on his arm, the fabric of his sweater soft and warm beneath your fingers.
“I’m so sorry, Harry. I had no idea.”
He looked at your hand for a long moment, and you wondered if his mind had gone somewhere far from the room, the bar, the entire city, as he stared at the way your manicured fingers curved lightly against his sleeve.
“Yeah, well,” he finally said, tipping back his drink to his lips, “No one was supposed to. And now she’s all over the tabloids.”
You smiled ironically, though it didn’t quite reach your eyes as you pulled away from him. “Right next to little ol’ me, the spoiled party girl who can’t go one day without ending up in Gossip Girl’s daily roundup.”
That pulled a small laugh from him. You took your martini and clinked the glass gently against his, both of you drinking in quiet solidarity.
After a moment, he glanced sideways at you. “So… what’s your plan?”
You exhaled, setting your drink down on the bar top with a soft clink. “According to my parents? Settle down, find a man who can ‘reel me in,’ and fix my image. Make me palatable again. Maybe get a job.” You gave a humorless laugh. “They’re cutting me off for two months to prove I can be respectable.”
His brow lifted slightly, but he didn’t interrupt.
“I’m just... tired,” you said, quieter now. “Tired of performing, of being their favorite liability. I feel like livestock at a charity auction—dressed up, shown off, never actually listened to. God forbid I enjoy myself or go to one little party. Then I’m reckless, I’m a shame. They never…I don’t know. They expect me to be so perfect and that the only way I’ll be respected is if I’m with a man.”
You sighed long and deep. You swirled the last sip of your martini around and shot it back in one last gulp. Staring deep into your glass, you swished the last dregs of alcohol in your mouth before swallowing it. You knew he was still watching you, could feel that piercing stare burning the side of your face.
“I might have an idea,” he said, quiet but sure.
You turned to him slowly, a little suspicious. “Oh no.”
He didn’t smile or look like he was mocking at all, he just leaned back in his seat, calm and composed.
“Date me.”
You blinked, coughed, and full on choked on your drink, your own spit, you weren’t even sure. You grabbed a napkin, pressing it to your mouth as your eyes watered, looking at him incredulously.
Harry raised a brow, unbothered. He sipped his tequila like nothing had happened. “Not the worst response I’ve ever received.”
“Are you serious?”
“Entirely.”
You kept staring in disbelief before one final cough and a short and disbelieving laugh. “Harry, come on. Why in the world would I do that? You’re... what, like, a thousand?”
He winced with exaggerated offense. “Not quite.”
You shook your head, “Don’t get me wrong, you’re… attractive. In that polished, middle-aged politician kind of way.”
“Wow, really digging the knife in now. And for the record, I’m forty five.”
“I just don’t see how this helps me.”
He set his glass down, folded his hands, and turned toward you. The amusement left his face, replaced by something quieter like intention.
“Because I can give them exactly what they want. A man who speaks their language. Brunches, art auctions, opening nights. I understand the performance. I know how to present well. You let them believe you’ve finally come to your senses, and perhaps the pressure eases. Perhaps your father gives you back those accounts of yours.”
You frowned, suddenly wary. “And in return?”
He paused for a beat. ““In return, you help me shift the spotlight. Keep Camilla out of the tabloids for a while. If people are busy watching me with a girl like you, they’re not digging into her while she gets the help she needs.”
There it was. A girl like you.
You stared at him, something sharp and sour curdling behind your ribs.
“Oh, I see. Because I’m already such a disaster, so what’s one more headline? One more joke?” you stood, grabbing your phone and snatching your black clutch bag, “What’s one more public humiliation for the girl everyone already thinks is a braindead waste of space. Perfect to hide your family dirt behind, right?”
“Wait—”
“No, fuck you, Harry.”
You shoved your chair back hard enough to scrape against the floor, tossing your napkin onto the bar without looking at him. Your heels struck the glossy wooden floor with every step, each one echoing louder than the last, the heat in your chest pulsing toward your throat as you walked out.
Throwing open the door to your bedroom, you flung yourself onto the bed without bothering to take off your shoes. Your body landed hard before sinking into the plush silk duvet, letting it swallow you whole. The room was so quiet, so clean and polished and perfect, everything you felt like you weren’t. Everything you were supposed to be. Your breath hitched once, then again, and then you were really crying. Hot, furious tears spilling into your pillow like a little girl.
Because of course that’s all anyone ever saw now. A spoiled, stupid, dramatic, disposable little girl. The perfect distraction, the party girl. Always staying out late, showing up on Gossip Girl’s headlines day in and day out, always saying the wrong thing at events and making it all look so effortlessly trashy. You were nothing but a walking headline in designer heels to them, and it hurt. It really fucking hurt.
Your phone buzzed in your hand, and you threw it clear across the room before even bothering a single glance. It bounced off your pile of half-unpacked Chanel shopping bags from two weeks ago and landed face-up on the floor. A second later, it lit up again. This time, Blair.
You peeked over the side of your bed to look as the notifications came in.
You sniffled, wiped your eyes with the sleeve of your cardigan, and hit call before you could stop yourself.
“Finally,” Blair answered exasperatedly, “I’ve had to watch you get publicly dragged across the entire internet without your commentary, and you completely ditched me today! Where have you been?”
You didn’t say anything at first, trying to soften the tightness in your throat.
“...Hello?”
“B…” you choked.
There was a pause, then her voice softened. “Aw, babe.”
You laid back, pressing your hand to your forehead while you let everything spill out of you. “Everyone thinks I’m a joke. My parents are going to cut me off, I just stormed out on Harry Castillo, Chuck is texting me for fucking drugs again.” you breathed in shakily, “And I’m so sorry about Greece, B.”
“What the hell were you doing with Harry?” Blair said, and you could picture her perfectly scrunched nose and ruby red lips pulling into a grimace, “Well, you have always had a flair for theatrics,” she said with a sigh, then quickly added, “but no one pulls off self-destruction in vintage Galliano quite like you.”
You let out a soft, wet, miserable laugh.
Blair sighed again through the phone, “Okay, listen, you are not a joke. Maybe a little dramatic, maybe a little insane and allergic to consequences, but you’re not a mess. I don’t care about Greece, I just care that you’re okay. We’ve all been through one thing or another. Do you remember when Gossip Girl told everyone I’d slept with both Nate and Chuck in one week? I threatened to move to France over it!”
You leaned back against the headboard, breathing slow. “God, yeah, that was so long ago I totally forgot.”
“Exactly. So go dry your tears, put on a hair mask, and for God’s sake, block Chuck’s number again please.”
“Do you wanna talk about why you were mad at him at your party?”
“Not today. We’re talking about you right now.”
You nodded even though she couldn’t see it. “Okay. Thanks, B.”
“Don’t let these jerks decide who you are, okay?” she said with a softness that she rarely let anyone see, “You’re not just what people post about. You’re my best friend and actually a good person, which none of these assholes can say about themselves.”
You smiled, watery and grateful. “Love you,”
“Love you more, babe.”
You hung up with a breath of something close to relief. For a moment, the silence was still, but less crushing.
You stared at your phone, swiping through your contacts and hesitating before you pressed Harry Castillo.
It rang once, and then again as you held your breath.
“Hey, kid,” he answered, “Listen, I’m so sorry—”
“Are you busy tomorrow morning?”
There was a pause.
“I can… move some things around,” he said slowly, “Why?”
You glanced out the window at the Manhattan skyline still lit up in its usual cold, glittering arrogance. “Meet me at Sant Ambroeus. Upper East Side. Nine.”
There was another pause before you heard a low exhale through the phone.
“Alright,” he said. “I’ll be there.”
Chapter 2: RingGate
Summary:
After a carefully crafted meeting over coffee, your public debut with Harry unfolds better than you ever expected. Each event slides effortlessly into the next as the plan is executed, performance convincing, and everything seems to fall into place exactly as you intended. And yet, you never could’ve predicted the effect it would have on you.
Notes:
(See the end of the chapter for notes.)
Chapter Text
You weren’t entirely sure why you’d called Harry back.
Well, no, that was probably a lie. You knew exactly why.
Harry Castillo made sense in a way no one else did. He was everything your parents meant when they spoke about a ‘good man’ to ‘settle you down’. He was sophisticated and predictably traditional, he came from a wealthy family, understood reputations and legacies, and didn’t have a scrap of dirt on him being seen at coke fueled yacht parties. Just nice tailored suits, understated luxury watches, and generous golf outings with potential investors.
But there was something else, too. Something that made him even better than all of that combined.
Harry was old enough to make anyone seeing you on his arm do a double take. Old enough to raise eyebrows. And you liked that. Hell, you loved it. Because while your mother would probably sing the praises of dating a nice, rich man with so much generational wealth he could bury you in it, the second she would see it was him, you could almost picture her face falling.
The Castillo name always earned a reaction in your family. Some long standing rivalry between your father and his, some sort of stock market tension or power play. Your mother always made a face as if the name sounded spoiled on her tongue and your father always got a set in his jaw at the briefest mention of Castillo Investments. And though your families orbited each other for decades, running in the same circles and sharing the same tables, they never managed to sit comfortably side by side.
So yes, Harry was perfect.
Because if you had to play by their rules, you’d make sure it still felt like your own game.
He looked the part now, sitting across from you in his crisp button down and open tailored blazer, the espresso cup held delicately between two fingers. The drink had long gone cold, but he swirled what remained, mulling over something in his mind. You were halfway through your latte, bringing it to your lips for another slow sip.
“So,” he said, voice low and thoughtful, “we’re agreed on hand holding?”
You nodded, watching him over the rim.
His eyes didn’t leave yours. “And…kissing?”
You set the mug down with a soft clink. “It’s supposed to look real, isn’t it?”
“Of course.”
“Real relationships don’t shy away from touch. I think a few public kisses are okay.”
He nodded back to you, “Just…you’ll have to let me know when you feel uncomfortable. If it gets to be too much.”
“Same to you. I don’t want to look like we’re in some rom-com soap opera.”
He leaned back in his chair, finally setting down the espresso cup with care. “I think you’ll find I’m quite good at moderation. But for clarity’s sake… what is off-limits?”
You considered for a moment, brushing a crumb from your napkin. “I mean… I guess the only rule I really care about is not humiliating each other. I seem to do that to myself enough as it is. So no divulging about us in interviews, no winks or jokes about the bedroom. If people ask, they can assume what they want. But we don’t talk about it.”
Harry nodded, his gaze steady. “Agreed. No innuendo, no details. Private things stay private.”
“Yes,” you agreed, your stomach doing a little flip at the thought.
“How long do you see us doing this for?” he asked.
You took a beat, thinking. “I only need eight weeks. By then, my family and I will be in the Hamptons hosting the annual Midsummer White Party—you know, everyone in white, garden tea, obligatory polo matches, and networking paraded around as philanthropy.”
Harry smiled, knowing. “Ah, yes. The crown jewel of performative generosity.”
You lifted your cup in mock salute. “Exactly. So if that works for you, we can bow out gracefully then.”
Harry nodded, “That should work. Camilla should be back by then and will most likely be attending. So the timing lines up.”
“Perfect,” you said, setting your cup down with a soft clink. “She can blend in with the party, and we can quietly let the news of a breakup make its rounds and...go on with our lives as if none of it happened.”
"Sounds very civil," he murmured, and then, eyes finding yours again as he sipped his espresso, “And when questions get asked about when we started dating?” he added.
You perked up. “Actually, I was thinking about that. I might have an idea.”
“Oh?”
You grinned. “The Met Gala. I’m already on the list, and so are you. I’m thinking, what if we made our public debut at the afterparty?”
“You and after parties, huh?”
You rolled your eyes, “It would be a good place to be seen together, and then if some civilian takes a photo of us cuddling in a booth, I think that would sell the thing perfectly. Rather than playing it up on the red carpet which might look more forced.”
“That’s next week, is that too soon for you?”
“Not at all. In fact–”
You reached across the table, gently taking his hand and adjusting the way he held his coffee cup. You tilted his fingers slightly, so that the emerald ring on his finger caught the light just right, gleaming against the white ceramic.
He gave you a curious look. “What are you doing?”
You brought your own latte closer, arranging your hand just so, both of you touching the handles of your mugs, your nails freshly painted and perfectly visible. You snapped a photo.
“This,” you said, opening Instagram, “is called a ‘soft launch,’ Harry,”
“Soft launch?” he asked with an amused grin.
You didn’t look up. “It’s where you show just enough to make people wonder who you’re with, but not enough to confirm anything. You post it to stories and let the speculation do the work.”
He huffed a quiet laugh, clearly entertained. “You really have this down to a science.”
You tapped through the filters without much care. “You said you wanted a distraction, right? This is how you make a splash without stepping outside.”
He leaned forward slightly, studying the image on your screen. “No one will know that’s me.”
“That’s the point,” you said. “Gotta keep it mysterious at first.”
He watched you with something that might’ve been admiration, or at the very least amusement. “You’re not what I expected.”
You smiled, “Would’ve been quite boring if I was predictable. Besides, you don’t want calm. You need chaos, and it just so happens the chaos you’re looking for is dressed in Chanel.”
That earned a real laugh — not the polite kind, but a rich, unguarded one that curled warmly at the edges. His eyes crinkled when he smiled, and for a second it made your chest pull in a way you hadn’t expected.
“Alright then,” he said, lifting the last of his espresso in a little toast. “To soft launches.”
You touched your mug to his and took a sip, the two of you smiling at each other over the rims.
You were rather pleased with yourself as you sat down at the table marked with your family name. The tablescape was decadent with pink and white flowers, crisp linen pressed to perfection beneath the gleaming gold flatware and bone white china. Tiny menus rested at each place setting and were printed on thick, textured cardstock with blush borders and embossed initials. Mimosas floated past in crystal clutches, delivered by white-gloved staff as the bridal shower brunch officially began beneath a silk-draped pergola on the Van der Woodsen terrace.
A harpist played delicately in the background, drowned only by the clinking of glasses and happy conversation around Serena. She was absolutely glowing in her white floor length gown and long white gloves, the essence of bridal straight from a magazine.
But it wasn’t the atmosphere that had you feeling so content. No, the smile tugging at the corner of your lips was from the fact that you’d sent the bait and people were flocking to it. Your soft launch with Harry had gone perfectly. You went unnoticed in the coffee shop but public online, it was purposely vague and yet sparked obsession across Gossip Girl and your DMs. Your plan was working. And across the table, it made your mother’s glare taste even better.
“Honestly, you think you’d want to actually be on time given the circumstances.” she scoffed as she aggressively snapped her napkin across her lap. Her greying hair was scraped back into an uptight bun, silver Tiffany hoops glittering in her ears and a beautiful, fresh look to her makeup. She was the picture of nobility, even as she sat across burning daggers into you.
And you too looked put together, good enough to pretend our weekend scandal never happened. A gauzy, floor length floral dress tickled your ankles, with woven wedges and golden teardrop earrings to accompany your understated look. But you could still feel the eyes, the whispers, the people around you looking over.
You knew your headline wouldn’t die with a simple coffee date exposition.
“I wasn’t even that late,” you muttered, sipping at the bubbly flute of champagne and orange juice. The look she gave you doesn’t go unnoticed, but it was cut off by another voice behind you.
“Did you really block my number again?”
You didn’t even have to turn to see who it was.
“Are men even allowed at these things?” you asked your mother flatly, ignoring the voice behind you.
Your mother exhaled, “Charles,” she said in greeting, though tired, “thank you for joining us. But yes…usually it is just the women who come to these.”
You glanced over your shoulder to see your brother with his hands gripping the back of your chair. Impeccably dressed, a crisp blue blazer and freshly cut hair. Of course, he also had a faint white dusting beneath his one nostril.
“How’re the donuts?” you smiled sweet as syrup, using your code for wipe your fucking nose, dumbass.
He clocked your meaning with a swipe to his nose with the back of his hand. “Delicious,” he murmured with a mocking smile, reaching for a glass of champagne like it was a handshake.
“But seriously,” he added as he flopped into the seat beside you, “are you mad at me or is this about your Girls Gone Wild debut?”
“Can people please stop calling it that?” you whined into your hand, covering your face, “I especially don’t need to be hearing it out of my own brother’s mouth, Chuck.”
He shrugged, “Kind of iconic, sis,”
“Charles.” your mother hissed with a scowl.
“Where’s B?” you asked him, hoping to god for a change of subject.
Chuck didn’t look at you as his jaw tightened and he stared out onto the terrace.
“Busy, I think.” he finally said.
You narrowed your eyes, “Busy with what? I just talked to her last night. She’s supposed to be here too.”
He leaned back in his chair and downed the rest of his glass. “I didn’t ask. She said not to come over last night, so I didn’t.” His voice was casual, but you knew him too well, there was a crack in it, right under the surface.
You didn’t press, you rarely did. It was their thing, whatever strange, codependent gravity held them together all these years. You’d long since stopped trying to understand it, and it wasn’t worth messing into anymore, even if it was the strangest feeling in the world: having your brother and best friend dating, that is.
But before you could say anything else, you felt a shift in the air, could smell warm perfume and that glowing Serena energy that always preceded her like a weather front.
“There you are!” she beamed, sliding up behind your chair and throwing her arms over you. You stood automatically, turning into her embrace, your arms sliding around her waist in return. Her hair brushed your cheek, smelling clean and floral and always so impossibly soft, and for a moment it felt like being sixteen again, sneaking out of benefits and charity galas just to smoke in the park and talk about boys you’d never marry.
She squeezed you once more than necessary.
And then, right beside your ear, voice low and lilting, she said, “Harry?”
You pulled back, blinking. For a second, you forgot where you were. She was smiling tightly, eyes bright enough to register the glee beneath it all. Your pulse spiked.
She knew. You didn’t know how, but she knew.
She gave a tiny nod, conspiratorial, and you mirrored it automatically, your body moving before your brain could catch up.
She giggled, delighted, and pulled you back into her arms
“I won’t tell a soul until you’re ready!” she whispered like it was sacred, “I recognized the Darius ring immediately!”
Your stomach dropped. Because if she knew, if she could identify it from a vague, cropped, untagged post over morning coffee... then everyone else wasn’t far behind. You’d set the match and the fuse was lit.
It was only a few seconds that you held each other there, but as you let go of each other you realized your hands were clammy when you reached for your champagne glass. You’d wanted this, you’d pictured how it’d go, when people would finally figure it all out and the gossip would start. But it was another thing to see the knowing in Serena’s eyes. To realize it had worked.
And the nicest thing about her was that she never asked about your messes or pressed you to do better or change your ways. She had her own fallouts once, and you were each other’s favorite bad influence until she got help junior year and started using words like boundaries and healing. But even now—clean, radiant, engaged—she wasn’t sanctimonious. She never needed you to explain yourself.
She just watched, knew, kept secrets like a dragon keeping its jewels. And she didn’t miss much, least of all a man’s ring.
The following week, you arrived at the Gala with your nerves fluttering beneath a glittering, bespoke Gucci gown. As the car crept behind a long line of black SUVs outside the Met, you ran your hands over the hand-sewn jewels stitched across the fabric, trying to steady yourself. The fabric clung like a second skin, sheer and opalescent, dusted with crystals that caught every flicker of light. Soft tulle spilled from your hips in delicate, weightless layers, each one shifting like smoke when you moved. The bodice swept off your shoulders in an ethereal curve, barely there, as if the entire dress had been spun from stardust and breath.
Outside the windows, camera flashes strobed like lightning. Journalists, paparazzi, and red carpet interviewers stood pressed against barricades while celebrities floated past them, their stylists, managers, and handlers hovering just out of frame. Everything looked exactly as it always did every year, controlled and perfect and expected. But something about this time felt heavier, almost electric.
Maybe it was you, maybe it was the buzz of cameras flashing in your face while you were sober this time. Maybe it was the fact you and Harry were going public tonight. The thought of him made your stomach turn and flutter into your lungs.
The moment your driver opened the door, everything shifted. The hum of the carpet swelled into a roar with the snaps of camera flashes and sharp cries of your name cutting through the night. From the left and the right, voices shouted, whistles pierced the air, all of it crashing toward you in a dizzying rush of flashbulbs and frenzy.
Typically, you just waltzed into these without so much commotion, just a pretty daughter of a major donor to the museum. But tonight there was no chance you’d sneak by with only one or two photos. At least this time your dress, though it clung to every curve, was full coverage. Elegant and thoughtfully styled and tailored to your body. Not like last Saturday when your nipples made headlines.
Your heels hit the carpet and you glided forward, plastering your best soft smile across your face, though the redness in your cheeks was hard to miss. You didn’t stand for photos, you kept moving, kept walking, because you thought your knees might give out if you didn’t.
Just find your family, find your table and your family and just sit before you throw up.
And then, once mercifully inside the grand doorway, a softer, elegant buzz fell around the room and you let out a long breath. Crystal chandeliers glowed above long tables dressed in gold and white, set between marble statues and famous paintings. It was breathtaking, curated within an inch of its life.
You spotted your mother and father at a table across the room and began to move towards them, when you were suddenly stopped short. There, stepping directly into your path, was a woman with a sleek, dirty-blonde bob and an icy blue coat draped over her shoulders. Her sequined gown shimmered with an elegance that commanded a room without question.
“Anna-!” you blurted, “Ms–Ms. Wintour, how are you?”
She didn’t smile or even reply to your greeting. Her eyes were like sharp daggers through silk.
“Miss Montclair,” she said crisply, “You were removed from the guest list earlier this week due to recent…events.”
The words hit like a slap across the face. You almost wish she had slapped you instead.
Your mother’s words from last week rang through your mind as you stared into Anna’s cold, green eyes.
You can forget about your cover with Forbes. Vogue sure isn’t going to take you back.
And here was the truth, standing in your path— the editor and chief of Vogue herself telling you that you were no longer welcome.
“I—what?”
“Your family is, of course, still welcome. I believe they’re in their seats right now. But you were struck from the official list.”
You didn’t even realize how tight your hands had curled until your fingernails pressed so hard into the palms of your hands you thought you might start bleeding. You glanced over her shoulder at your mother who was suddenly not looking at you at all.
So this was how it happened. Your first public appearance since the scandal, in front of every person who mattered, and you were going to be escorted out.
You felt your chest tighten—your throat caught, eyes already hot.
But then, there was a warm hand at the small of your back.
“Ah, Ms Wintour, thank you for finding my date.”
You turned, and there he was.
Flawless in all black Tom Ford, tie knotted perfectly and not a single hair out of place. He stood beside you, his chest emitting warmth as it brushed your shoulder, steady and calm as his eyes met Anna’s without blinking.
“Mr. Castillo–” Anna said, surprised.
“I’ll take her to her seat now, thank you,” he said calmly.
“You’re attending together?”
“Yes,” Harry said, “she’s my guest tonight.”
There was a long pause as Anna looked between the two of you, her eyes momentarily caught on the way his arm was around you.
“Very well,” she said with a nod, stepping back. And just like that, she turned and disappeared into the crowd of curated faces and brand sponsored gowns.
You stood frozen, watching her go.
You heard Harry’s voice, so gentle beside you, as it brought you back to the moment, “You okay?”
You took in a gulp of air, remembering yourself, and nodded. He didn’t say anything else before gently guiding you forward, hand staying at the small of your back, through the velvet ropes and into the glittering madness of the main hall.
“You look really nice tonight,” he whispered in your ear as you closed in on the table with your family. It was decorated with white orchids and gold place cards, and you could just make out your name when he stopped you. He turned you towards himself, his hand coming up to your upper arm, steady and gentle.
“Thanks,” you swallowed, but your voice felt so small. You weren’t sure all you were thanking for, but it was for everything, really. For saving you from social torment, for guiding you through the buzzing crowd when you could barely catch your breath. Maybe even for the compliment.
He smiled, just slightly, then lifted a hand to your chin. His thumb brushed softly against it before he glanced behind you. He nodded once, tight, toward your family before turning away and melting into the crowd.
You watched him for a long moment, already being stopped by some hedge fund heir in a pearl bespoke tux.
Sinking slowly into your seat, you could already feel your mother watching, your father’s eyes on the back of Harry’s head.
Both of them confused, and more than anything, furious.
“Care to explain what exactly that was?” your mother said tersely over the rim of her champagne flute.
The swell of the room came back to you as if you were stuck in a whirlwind and finally climbing back out. Around you, the long table buzzed with idle chatter as guests admired the floral arrangements, whispered about other guest’s attire, and traded gossip beneath the glow of crystal chandeliers.
“Can we do this later?” you managed to say, barely above a whisper. You weren’t sure you had it in you to explain everything in the midst of your near social exile.
Your mother opened her mouth to object, but your father cut in first. “She’s right. Later.” and then his deep, stern eyes were on you, “But I expect to hear about it.”
You gave a small nod, grateful for the reprieve, even if temporary, just as Blair slid gracefully into the seat beside you.
She looked like she’d walked out of a fashion editorial, or perhaps an old film—her deep plum gown cut sleek and sharp across her collarbones, the satin catching the light like still water. A band of silver sequins wrapped low around her hips, subtle but stunning, accentuating the drape of the fabric. Her hair was curled softly around her shoulders, her expression calm but knowing.
She didn’t say anything at first, simply reached for her water, took a slow sip, and then leaned in slightly toward you. “You looked incredible,” she murmured. “Even with the parental firing squad.”
You smiled, immediately at ease with your best friend beside you.
“I’m so glad you’re here, B.”
“Please. Like I’d miss this circus. Besides, half of these people are wearing Waldorf gowns, you think my mother would let me miss out on her chance to boast?”
You exhaled, shoulders lowering just slightly. Around you, the room went from a buzzing livewire to hushed tones and the scrape of chairs as everyone took their seats. With Blair beside you, you almost felt like you could face everything the night had in store.
And when all the glitz and glamor dissolved into a haze of flashbulbs and farewells, you found yourself grateful to slip away from the velvet ropes and instead, behind a nondescript steel door with music blaring from inside.
The speakeasy was low-lit and smoky, filled with only the right people. No flashing cameras or press agents. Just velvet booths, a marble bar backlit in soft amber, and a jazz band in the corner with a singer who looked like she was plucked straight from a 20’s Hollywood movie. You let your shoulders drop as the door swung closed behind you, the noise of the outside world sealed off completely.
“Oh god,” Blair muttered beside you, adjusting her diamond earrings. “I see Chuck.”
You rolled your eyes. “He wasn’t even at the gala.”
“Exactly,” she hissed, already backing away. “Classic Chuck, always ruining my night when it’s just about to get fun. I’ll find you later, okay?”
You nodded, amused, and made your way toward the bar.
You ordered your dirty gin martini—Ice cold. Like frostbite. I want my hand to hurt just holding it. The bartender smirked as he went to make it, his gaze lingering too long at your neckline. You stared back blankly until he finally turned away.
Your fingers skimmed your phone screen as you leaned into the bar, scrolling through the expected: red carpet recaps, Vogue slideshows, slow-motion video of someone’s Glambot from the night. You caught sight of yourself in a carousel of photos—you, for once, not for scandal, but for style. A quiet thrill settled in your chest.
Then came a voice, low and close.
“And how many martinis are we thinking for tonight?”
You didn’t have to turn. “You really do have a knack for sneaking up on me tonight, Harry.”
He settled in beside you, his presence tall and steady and gleaming at the edges—like some sleek, expensive car pulling up beside yours at a red light.
“Only one,” you murmured to answer him when he didn’t say anything. “Just enough to take the edge off.”
He lifted his own glass, ice clinking faintly. “Tequila.”
“Of course,” you said, “Can’t help but wonder what that says about you.”
“Dangerously misunderstood,” he replied, deadpan.
You smirked.
The bartender set your drink down with a soft clink, and Harry’s hand brushed your lower back as he gestured toward a booth across the room.
The leather was black and glossy beneath the dim gold light that bounced from the sconces along the wall. Harry slid in first, and you followed, settling beside him as his free arm draped behind you along the top of the loveseat. The heat of him was immediate as he moved in closer. He smelled like sandalwood and amber, sharp and expensive. You could feel the weight of his presence, could hear the shift of his jacket as he leaned in. He was close enough to count the gold flecks in his dark, endless brown eyes.
“Did you have a good night?” you asked, keeping your voice smooth even as your pulse ticked higher. You tried not to shift under the burn of his nearness, tried to ignore the way your skin prickled where his breath grazed your cheek.
He nodded, his thumb lightly circling your wrist as his hand drifted closer on the table, casual but intentional.
“You're a natural,” you added, tilting your head up at him, trying to make it look like flirty banter to any wandering eyes. God he was close.
He mirrored your tilt with a slow, knowing smile. “I saw the bartender looking at you.”
You glanced back toward the bar and caught it. The glint of a phone, half-concealed behind the ice bin. Filming.
“I think he’s recording us,” you whispered when you looked back up to Harry. You leaned in slightly, your voice like a secret.
“What do you say we get this show on the road?” he asked.
You faced him full, heartbeat quickening. “Okay.” you said, softer now.
“Come closer,”
You set your glass down. Condensation kissed your fingertips as you brushed your hand along the front of his tuxedo jacket, pulling him toward you. The room seemed to fall away—replaced by shadows, low voices, and his warmth beside you.
“I’m going to touch you now, okay?” he asked, and when you nodded, your throat too tight to speak, he added, “Let me know if it’s too much,”
His breath fanned over your face, smelling like spearmint and alcohol and that oud wood cologne as his fingers trailed from your wrist to the bend of your elbow, cold from the glass of his drink. Goosebumps bloomed across your skin like reflex as he moved in closer—so close his nose nuzzled yours, then traced the high arc of your cheekbone, lingering at your temple before slowly sliding into your hairline, hidden from sight. His breath was warm, slow, steady.
You didn’t mean to grip his lapel so tightly. But your fingers curled anyway, holding him closer than maybe necessary, your knuckles brushing the silk pocket square as if searching for something to anchor you.
Your eyes fluttered shut and he hovered at your ear, close enough for the edge of his jaw to graze your skin.
And then, just when you thought he might pull back, he said:
“Good job,” voice low, neither smug or insincere. You weren’t sure if he meant your touch, your composure, or the flush you could feel blooming high on your cheeks. Maybe all three.
You drew back slowly, your hand falling from his jacket as your eyes lifted to meet his. But not before they lingered for a second too long on his mouth. When you looked up again, his gaze was already there, steady and a little cheeky, the burned caramel of his eyes catching the soft light and holding your reflection inside them.
You offered him a smile, “Not bad for our first show, huh?”
He shifted slightly, his eyes flicking to the table just as your phone began to buzz beside your glass.
“You tell me,” he said, his voice lighter now, a smile playing at the edge of his mouth.
You picked up your phone, and for a moment, your smile threatened to widen. But you caught it quickly, schooling your expression into something more performative—eyes wide, just the right amount of shock, thumb frozen above the screen like you weren’t expecting exactly this.
Across your notifications, Gossip Girl was already doing what she did best.
“I am trying very hard not to look excited right now,” you whispered, keeping a hand over your mouth so no one could see your smile.
“Why, have I gotten you all twitterpated?” Harry said in your ear, reading the screen.
“Harry, it’s the twenty-first century, no one says that shit anymore,” you said, letting your smile break free as you dropped your hand to reach for your drink and took a sip. The alcohol was cooling against your burning skin, your parched throat, your heavy tongue. Everything felt so real suddenly, like it was snowballing further and further as you saw people around you reaching for their phones, reading their notifications, their eyes finding you in the corner of the room.
“So yes, I think we put on quite a show, don’t you?” Harry said, lifting his glass to his lips.
You leaned back just slightly, letting the confidence settle in your bones. “Close it out with a standing ovation?”
He laughed softly, then set his drink down and reached for you again, nodding. His hands found your waist and tugged you in, your shoulder bumping against his chest. Without another word, he pressed a single kiss to the high point of your cheekbone. Just a small, sweet, calculated gesture. The kind that would photograph beautifully under dim lights of the room.
“How’s that?” he asked in your ear.
You blinked, caught off guard.
“I was thinking of something a little more exciting, but I think that'll do.” you chuckled, voice low, eyes flitting to his lips before settling back on his eyes.
“Can’t give them everything they want,” he said, eyes twinkling.
You huffed in amusement, but then quietly asked, “Can I return the favor?”
His eyes flicked to yours, just a fraction of hesitation before he gave a subtle nod that was measured and careful, like everything he did.
You leaned in, pressing your lips to the edge of his jaw, where his five o’clock shadow covered his skin. It was brief and camera friendly, but still, the second your mouth met the warmth of his rough with scruffy face, your stomach gave a tight and fluttering twist.
“I’m starting to think you’re better at this than me, Castillo,” you murmured, your lips brushing just close enough to make sure he felt the words.
He smiled, soft and smug, “Wouldn’t dream of it, Montclair.”
Notes:
okay yes chuck is your brother and im pretending he doesn't have the last name Bass in this!! sorry bass lovers!! his dad sucked anyway!!
Chapter 3: Kiss Cam
Summary:
An argument over breakfast lights a new fire under you before another staged date with Harry. But you’re not as good at this as you thought. Feelings creep in, an interview falls apart, and Gossip Girl is always there to twist the knife.
Notes:
gentle warning: reader has a panic attack in this chapter
Chapter Text
It was almost like deja u, sitting at the long, stretching lacquered table at the center of the dining room. Morning light spilled through the large windows as always, hitting the marble floors with soft golden rays. It was a nice change compared to the last time you were sitting here, being blinded by sun rays and vodka twisting in your stomach. That was progress at least.
Or, so you thought.
“Why do I have a feeling this is becoming a pattern?” your father’s voice sounded with a sigh as he sat at the head of the table beside you, dropping the newspaper beside his coffee.
There was a grainy photo there, pulled straight from Gossip Girl’s Met Gala afterparty tip. It was the same one that you received in a video: you and Harry curled into each other in a dark corner booth, his mouth close to your ear as you giggled like he’d said something wicked, your smile warm and flirty. You really looked the part.
FROM SPECULATION TO SPOTLIGHT: CASTILLO AND MONTCLAIR CONFIRM RELATIONSHIP
Your mother entered the room shortly after your father, her eyes pointedly kept away from you as she sat, pouring her tea silently in her bright green Lululemon. You sent another grateful prayer that you weren’t hungover this morning, knowing the migraine you would’ve gotten just by simply looking at her.
“And why,” she began, her eyes finally falling on you in a narrowed gaze, “in god’s name is it with Harry Castillo of all people?”
You didn’t look up as you stirred your coffee, the spoon clinking delicately on the rim. “He’s nice, I thought you’d approve.”
“Approve?” she parroted, “He’s almost twice your age.”
“Harry’s a great guy,” you said simply, “He’s successful and kind, he understands me.”
“That’s very sweet, pumpkin,” your father added, “but we asked you to stay out of the headlines, not make the news every morning.”
“He’s bored,” your mother went on, and you wondered if it was more to herself than you. “That’s what this is. A midlife crisis with press coverage.”
You let out a short, tight breath. You knew this argument was coming, knew how you wanted to play it, too. “I try to make you happy by getting out there, dating and seeing someone. And he’s respectful, established, everything you said you wanted and still, it’s not enough. It’s never enough.”
And then—and maybe it was petty, maybe you’d just had enough—you said: “No wonder Chuck never comes around anymore.”
The room went deadly still for about half a second.
And then the violent scrape of your mother’s chair rented the silence. She stood abruptly, her perfectly manicured finger pointing at you across the table, “Don’t you dare bring your brother into this!”
“Alright,” your father said quickly, palms flattening against the table in that weary peacemaker gesture he always pulled out when she got loud. “Sit down, darling. Please.”
She didn’t listen.
“End it.” she said forcefully.
You blinked up at her, “Excuse me?”
“End it with him.” she said, cold and sharp, “Before this gets worse.”
You tilted your head. “Worse for who?”
Your father shifted in his seat, eyes glancing between the two of you. “Let’s all take a breath—”
“No,” your mother cut in. “I won’t have her parading around with that man like this family is a tabloid punchline.” she pointed her finger at you again, “You think you’re being clever? You think this is some kind of game?”
“I'm giving you exactly what you wanted,” you said calmly. “Isn’t that the deal? Eight weeks, someone respectable, a cleaned-up image—”
“I will take away everything,” your mother said, her voice trembling with fury, her palms laying flat on the table now, leaning in. “Your cards. Your trust, you won’t have a cent to your name.”
You stared at her, something in you sparking. “Then do it. I’m already almost cut off from everything, what else is there to take?”
Your mother barked a harsh laugh, “Oh, please, you have no—”
Your father’s hand came down flat against the table, “Enough.”
She rounded on him. “You said—”
“I know what I said,” he interrupted. “And I also said we’d give her eight weeks. That’s what we agreed on.”
You looked at him, only slightly surprised. You knew he wasn’t defending you so much as just trying to keep the house from catching fire.
He exhaled slowly as your mother began to sit back down in her chair, her fingers slightly trembling with adrenaline as she picked up her tea to take a grounding sip.
“If this is real,” he went on, looking at you now, “and it’s not some ploy to get back at me and your mother, then fine. But show us. All of it, not just cozying up in a dark booth playing girlfriend over cocktails. I need to see real effort here, pumpkin. Make something of your life. I’d be happy to get you a position at the firm, to help you find a place of your own. But I need to see you trying. Because right now, this just feels like you’re throwing a tantrum in our faces.”
You swallowed dryly, the room going quiet except for the clinking of mugs on porcelain. Your mother’s eyes narrowed but she remained silent now, seething behind her teacup.
You smoothed your napkin across your lap, heart pounding, but your voice was steady. “Fine. I will.”
You and Harry had a scheduled appearance in Central Park that afternoon, and you met him at the East entrance just past the stone archway. Your flared jeans and a soft white knit sleeveless vest were perfect for the warm spring afternoon. The sweater, fastened neatly down the front with just enough left undone to feel fresh—not scandalous, but far from plain. Classy, but tailored. You’d never risk a Gossip Girl photo op without looking intentional.
Harry arrived in a tan button up with the sleeves pushed to his elbows. Casual and easy, and for a moment, you simply took in the way his hair curled a little looser today, less product, a little disheveled. His watch gleamed darkly at his wrist, something polished but understated. In his crisp jeans with brown loafers, he looked like someone to be admired without reaching for it.
“Hello,” you said, smiling as you approached.
“Hi,” he returned, leaning in to press a kiss to your cheek, light and warm in its curated intention.
When he pulled back, he paused just slightly. “That okay?”
“More than okay,” you replied, your voice even but bright. “Shall we?”
You offered him your hand, and he took it with an easy nod, gesturing for you to lead.
The walk was… surprisingly nice. You moved slowly down the paved paths, fingers laced as the wind stirred through the trees and the late afternoon sun filtered through the canopy in long, shifting lines. For a while, the performance faded into the background.
Harry was so easy to talk to with his low-voiced, observant, quick wit, always seemingly able to listen intentionally while adding a dry remark here and there that made you laugh. You found yourself telling him about your mother’s meltdown that morning, how she'd threatened to cut you off, how your father wanted proof you could be a functioning adult.
“And what did you say?” he asked, tilting his head as you passed a group of people walking dogs in matching coats.
You glanced at him, a smile tugging at the corner of your mouth. “I said fine. I’ll do it.”
He raised a brow. “Just like that?”
“There’s something exhilarating about being able to prove them wrong,” you said with a mischievous smile. He chuckled a little at that, but seemed to know there was more you wanted to say, so he waited.
You sighed, “I don’t know, though. Part of me wonders…if they have a point. I mean, I’ve never worked a day in my life other than brand deals on Instagram or showing up to events in a designer’s clothes. It would be nice to not be under their nose twenty four seven as well, to have my own place. To call it mine. Oh, and I even have an interview tomorrow.”
“That’s great,” he said genuinely, “Where?”
“The Times,” you replied, trying not to sound too proud.
He glanced over, impressed. “That’s very impressive.”
You smiled as you looked at the profile of his face. There was something about the way he said it so simply and so…sincerely that settled in you. You weren’t used to that. Usually, praise came with a caveat, a backhanded comment, a reminder that you should’ve done more. You squeezed his hand without thinking, and your finger brushed the gold band of his ring.
“You know,” you said, glancing down at it, “Serena recognized you. From the photo I posted. Our ‘soft launch’. I was surprised it took Gossip Girl so long, but she… she knew. Right after I posted it, at her bridal shower.”
You slowed a little, still looking at the ring, bringing up your clasped hands to look at it closer, “How would she know you by a ring?”
You felt him tense before looking back at him. His posture changed, and you saw how his shoulders tightened up, how the careful smile that usually touched his lips was gone.
Harry suddenly looked quite…uncomfortable. And you weren’t sure why, but that suddenly made your pulse spike.
“What is it?” you asked.
“Serena Van Der Woodsen…” he said quietly, biting his top lip, looking down at his feet, his free hand scratching at the five o clock shadow at his jaw. Your heart began to flutter into your throat, nerves lighting up. You pushed down the nerves, the thoughts of…what, you weren’t entirely sure.
“We went on a date or two,” he finally said.
You stopped short, “What?”
He looked a little sheepish, “It wasn’t anything serious,” he said, shaking his head. “A couple of dinners. Nothing meaningful came of it.”
You weren’t entirely sure what to say.
“Through Adore.” he added, “You know the matchmaking service?”
You nodded, stiffly. You knew of it, knew your friends that had tried it. The owner was one of your mom’s college friends, so you regularly heard the updates of marriages they’d tailored together, how your mom often begged you to add you to their roster.
“I told them I wasn’t looking to date anyone that young,” Harry said carefully. “This was years ago, and… a friend was persistent. Said Serena had just come out of a long-term relationship.”
You could still vaguely remember the times before Serena and Dan were engaged when their relationship was all sharp turns and slow recoveries. They were endlessly tangled in Gossip Girl posts and whispered rumors that always seemed timed to hit just when things were starting to feel stable. It had been dramatic, sure, sometimes exhausting to witness, but in hindsight, it was almost admirable. No matter how messy things got, they always found their way back to each other. Even through high school, through university, through making a life for themselves back in the city.
"Still, I agreed to a couple dates. She’s very nice, very charming."
“Much like you,” you said, and you didn’t realize how sad you sounded until it was already out of your mouth.
Harry offered a small, tired smile. “It became clear quickly we were looking for different things. We agreed to part ways, and I stepped back from the service after that. But yes — she would have recognized the ring. I believe she asked about it on our first date.”
You stopped, turning toward him, studying his face in the soft light. “I was wondering why I had never seen you dating anyone before. I mean…you’re so nice, so put together and not hard to look at, by the way—”
“Are you hitting on me?” he said with a sudden mischievous twinkle in his eye, his loose smile back on his face as he turned to you.
You rolled your eyes, giving his hand a playful tug as you smiled back. “Stop. I’m just saying… you’re a catch, Harry. Any girl would be lucky to have you. So why haven’t I seen you in anything serious?”
He looked away briefly, the smile lingering before it faded into something quieter. “Just never found the right person, I guess.”
“You’ve never been in love?” you asked, tilting your head.
His eyes found yours again—those warm, watchful eyes that always seemed so sure of themselves suddenly looked so unsure. Sad, almost, like the question had tugged on something old and partially buried.
“I—”
The flash of cameras cut him off with the sound of your name ranging out like a warning bell.
You turned fast, hand coming up instinctively to shield your face. Harry mirrored you, stepping in closer, his hand dropping yours to find your lower back, guiding you both away from the cluster of photographers.
“Crap,” you muttered under your breath.
“Shouldn’t we be happy to see them?” he asked, glancing at you beneath his hand.
“Under no circumstances could I ever be happy to see these assholes.”
Gossip Girl tips were one thing. They came from passersby, people sipping their coffee on a park bench or walking their dog and just happened to catch a glimpse of you. But people who made a living off invading your privacy with flashing lights, shouted names, and cameras always at the ready were something else entirely.
But when you looked back at Harry, he was smiling. Something sly and boyish tugging at the corner of his mouth.
“We could give them something to talk about,” he said with a teasing lilt.
You slowed, blinking at him through the slats of your fingers. “Are you serious?”
“I wouldn’t suggest it if I weren’t,” he said. “But only if you're okay with it.”
“Harry!” one of the photographers shouted over him, “Give her a kiss! C’mon, kiss her!”
You gaped at him, slowing down your gait. “You’re actually considering it.”
He dropped the hand from his face and stepped a little closer, his expression calm. “I’m game if you are.”
When you didn’t answer with words and only smiled at him, his own lips widened, the lines in his face deepening with a knowing kind of joy. He reached for your jaw, and you let out a surprised laugh as he pulled you in, his palm warm where it cradled your cheek.
God, his lips were so soft.
Softer that you’d expected, and warmer too. His mustache tickled your upper lip and nose, and he smelled like pine and something fresh, clean in a way that surprised you, so different from the oud wood of the night before. It was like catching him in a different season, a different light.
It was meant to be for the cameras, you knew that. Knew it in the way his hand held the side of your face that wasn’t facing the flash of bulbs, angled and calculated and strategic in every way. But still…
As his hand stayed cupped gently along your jaw, thumb resting just under your ear, something wriggled in your stomach. And he kissed you harder, longer, like he was playing a role with more conviction than expected. You refused to name the feeling fluttering through your nerves, reminded yourself that even has your fingers curled slightly around his bicep where you help him, that this was for show, for cameras. It wasn’t real.
But you couldn’t help but find yourself smiling through it, and when Harry pulled back, he was smiling too, your lip gloss faintly smudged on his mouth.
You reached up and brushed it away with your thumb, and he chuckled, fingers wrapping around yours again as he led you away down the path, flashes still popping behind you.
You absolutely were not thinking about the kiss from Harry as you stepped into the sleek, silver elevator on your way to the interview the following day. You were not remembering his crisp, forest-y cologne, or the way his mustache tickled your upper lip, or how his hand cupped your face as you pressed the button for the 30th floor.
And you were certainly not, under any circumstance, thinking about how badly you wanted to do it again as the elevator dinged for your stop.
Because, for the love of God, you needed to focus. You had answers to Top Questions Asked At Interviews rattling around your brain, half-memorized. You needed to remind yourself that this was a real opportunity and not a staged date or photo op for the next headline. It was nerve wracking, yes, but manageable. Especially since you technically knew the interviewer from a yacht party in Palm Beach last summer.
So when you stepped into the main reception of The New York Times, you were absolutely, unequivocally, without question not thinking about kissing Harry Castillo.
The receptionist greeted you and soon motioned you toward a set of double glass doors, and you followed her through a quiet corridor lined with framed Pulitzer winners, your heels clicking sharply on the tile. At the end of the hall, she held a small office door open for you.
You stepped inside, expecting to see Chloe—tan, fake boobs, and wildly overqualified for her position thanks to nepotism and generational wealth. The girl who once told you, barefoot on said yacht in Florida, that journalism was just a vibe, like, totally a vibe, don’t let anyone tell you you need experience.
Instead, you were greeted by someone else entirely. An older woman, maybe in her late sixties, sitting behind a stark black desk. Her hair was silver and pulled back in a low twist, her reading glasses perched halfway down her nose and a navy silk scarf was knotted at her throat. She reminded you a bit of your mother if she traded in the Lululemon for department store sale racks.
“Miss Montclair,” the woman said, standing only halfway as she extended a hand. Her voice was cool and clipped as she introduced herself. “I’m Margaret Lang. I’ll be conducting your interview today.”
You took her extended hand despite your confusion, “Hi, I thought I was meeting with—”
“Miss Hargrove was pulled into a meeting earlier than expected,” she replied briskly, already sitting down and gesturing to the chair opposite her desk. “Please.”
You sat, your black skirt covered ass hitting the seat harder than you intended. You smoothed it out and tried to smile. This was fine. After all, you’d prepped, at least a little. You had notes, you’d watched a couple videos. You had answers to things like where do you see yourself in five years? and what would your past coworkers say about you? She didn’t need to know you’d never even had coworkers before in your entire life.
“So, Miss Montclair,” Margaret began, lacing her fingers together over a thick, leather portfolio. “Tell me: what drew you to this role?”
You opened your mouth, then closed it again.
What drew you to the role?
You swallowed. The truth was... nothing did. Only that you knew people who worked here, that the household name The New York Times would keep your parents off your back, give you back your Amex Black Card, and potentially give you the freedom to get back to your regular life.
You cleared your throat. “Well, I… I’ve always had a deep appreciation for the written word.”
Margaret didn’t blink. “Mmhmm.”
“And journalism,” you added, like that somehow clarified anything.
Another pause.
You panicked. “I love words. And…and the paper.”
Jesus Christ.
Margaret made a small note on her pad.
You tried again. “I read The Times growing up. My family reads it every morning too.”
She looked at you over her glasses. “The digital edition or print?”
You froze. “What?”
“Print or digital?”
“Oh. Um. Both?”
Another note scribbled on her notepad.
“Let’s move on,” she said, mercifully. “Tell me about a time you overcame a professional challenge.”
Professional challenge. Okay, you could do this. You had something, had made sure to have this answer ready—you just had to dig for it in the archives of your brain.
The problem was, the only thing surfacing was that stupid kiss with Harry in the park. The way his hand had cupped your jaw, the flashbulbs, the sound of your name being shouted. Your nerves were fraying as you sat in this stuffy little office, with the whole of New York outside her window, and you could actually see Central Park from here. It didn’t help as you tried to push the memory away, trying to keep your nerves intact. But you could feel them coming apart at the edges, thin threads snapping inside your chest.
You tried anyway, forcing your brain to just think of something as you said, “There was a… a summer in Saint-Tropez. We lost WiFi on the yacht, and I had to send—”
“Let’s try another one,” Margaret cut in, voice still cool. “How would your peers describe your work ethic?”
You stared at her.
“Miss Montclair?”
“I… think they would say I show up.”
Margaret didn’t move, waiting for you to continue. You felt your hands going clammy as you wiped them on your thighs.
But still, you pressed on. “I always show up. I mean—I’m punctual. Not always, like, early. But… present. In a meaningful way. Emotionally.”
Another pause.
You were going down, you knew it. For the love of god, the Titanic had more grace than you did right now.
Margaret adjusted her glasses. “I see.”
You weren’t sure if she did. Or if she’d already decided to blacklist you from the entire building. She made another note, her pen barely scratching the paper.
She looked up again, perfectly composed. “One final thing, Miss Montclair.”
You straightened in your seat, hands clasped in your lap.
“I’ll admit, when your application first came across my desk, I had my doubts,” she said, her tone somehow both warm and cold. “Given the… recent visibility surrounding your name.”
You froze. Here it was, moment of truth.
She offered a thin, polite smile. ““Given the recent attention you’ve garnered—however unintentional—I had reason to wonder whether someone with your background would be the right fit for The Times. We take our values seriously here. But as I understand it, your family has a long standing connection to Mr. Lancaster.”
You blinked, slowly, recognizing the name, vaguely. Publisher, maybe? Owner? Someone old and powerful and usually in golf photos with your dad.
“And I must say,” she continued, flipping a page in her folder with clinical grace, “you do seem to have a talent for remaining culturally relevant.”
You couldn’t tell if she meant it with judgment or pity. It surely wasn’t a compliment.
“So here’s my question,” Margaret said, peering over her glasses. “If we were to bring you on, in what ways do you believe you could elevate our brand?”
You swallowed, forcing yourself to not bend under her serious, hawk-like stare. “I… I think I understand attention.” you began, maybe a little shakily, but you pushed through it, through the nerves and uncertainty, “Not in a performative way, but in the sense that I know how quickly a narrative can spread. What people respond to, what makes them stop and look.”
Her brow raised, fingers finally stopping, fully listening to what you had to say.
“I don’t mean that I want the attention,” you clarified. “I just… I’ve been at the center of it enough to recognize its power. And I think maybe, if I learn the right way to use that, I could channel it into something worthwhile. Something better.”
Margaret stared at you for a long time before nodding once. “Thank you, Miss Montclair. We’ll be in touch.”
Back in the elevator, the sleek, chrome-trimmed doors closed around you with a whisper, sealing you in a silver capsule that smelled faintly of eucalyptus and cold metal. You leaned against the mirrored wall, exhaling slowly as you tried to go over the interview in your mind, but the thoughts floated uselessly now, weightless and out of reach, as if once you stepped out of the office it was blacked out of your memory. She hadn’t cared about your goals or your education. She’d just wanted to see if the tabloid girl could sit still long enough not to embarrass her paper.
The elevator began its descent, and when you finally glanced down at your phone, the screen was already lit with notifications.
The ding of the doors rang again for your arrival to the ground floor, and you straightened reflexively, shoving the phone back into your bag, trying to collect yourself, to focus, to fix your expression into something less readable. But the moment the doors parted, the lobby lit up like a runway.
Flashes burst through the glass windows. Shouts echoed off the marble.
You blinked, half-frozen as the wall of cameras snapped toward you from outside. Faces you didn’t recognize, lenses trained like weapons, their voices merging into an unintelligible roar as they pressed against the building's glass front. They shouted your name, Harry’s name, asking about your date with him, about the kiss, if the wedding was next, if you were moving in, if you’d left your family behind.
The air thinned around you in an instant. It felt like being trapped, the walls getting closer and closer, their voices echoing through the glass as security tried to keep them back. Why were they flocking here? God forbid you showed up to an interview where Harry happened to work, was nothing sacred? Nothing for you to do without wondering if it was about a man? You wanted to scream, to throw your phone, your bag, your claws at them. But you felt frozen, you couldn’t breathe or think or move.
But finally you seemed to be able to feel your feet as another security guard approached, and you turned sharply, heels clacking loud against the tile, darting past the lobby desk without meeting anyone’s eyes. The hallway narrowed behind the steel elevators, leading toward a corridor, and you made for the farthest door marked for restrooms, not pausing until you were inside and the heavy door shut behind you with a thud.
Fluorescent lighting buzzed overhead, far too loud and sharp. The tile floor was cold beneath your heels, the walls a sterile pale gray that made everything feel more clinical than private. You locked the door behind you and made it to the sink, grateful for the single stall bathroom. You finally let yourself slump forward, palms braced against the porcelain as the room pressed in around you.
The air in the bathroom felt hot, even though the building’s AC was blasting. Your hands were shaking as you pressed them to your face, trying to block out the noise, the headlines, the questions. You’d thought the interview was the low point of it all, feeling like you would never be good enough for any of it, feeling so small and useless across from that old hag. But this, now, made it all feel worse. Like you were some creature on display, circling the same glass walls over and over, no way out.
You gasped for air but didn’t cry. You wouldn’t cry, you wouldn’t let them see the tear tracks through your foundation when you finally had the courage to leave. Your breath came sharp and shallow, the sound of it echoing too loud against the marble walls of the restroom. You pushed off the sink and sat on the closed toilet lid. You didn’t know how to move your limbs, arms curling around yourself, body stiff with humiliation and dread. Your phone vibrated in your bag—another text, maybe another photo, another reminder that your life belonged more to strangers than to yourself.
You fumbled for it anyway, nearly dropping it on the tile, barely glancing at the flood of notifications lighting up the screen. The first number you called was Blair’s.
It rang and rang and rang. And just when you thought she might pick up, her familiar voicemail started—“You’ve reached Blair, I–” and you hung up before she could finish, the sound suddenly unbearable.
You could call Serena, maybe. But she was knee-deep in wedding planning and you couldn’t stomach the idea of being that kind of friend. You could call your parents but…God, no. They’d only make it worse. Chuck? He was probably wasted somewhere on the West End with his buddies in an underground poker scene he loved so much.
Looking down at the screen, thumb hesitating just above Blair’s name, thinking maybe if you called again…but then moved on through your contacts. Past the ones who’d only make it worse, ones who never answered or only called when they needed something. That’s how it always was, so transactional, so superficial. You landed on the only name that felt equal parts safe and humiliating. You tapped it anyway.
It only rang once.
“Hello?” His voice came warm and low, casual like he’d just stepped out of a meeting.
You opened your mouth, but your voice didn’t come. You had to swallow down a sob, had to force your tongue to move.
“I—I’m in your building apparently,” you said, rushing the words out.
“You are? Why?” A pause. “The Times interview?”
“Yeah, but—” you couldn’t stop the wobble in your voice, the way your throat closed up. “I’m in the bathroom. I—I didn’t know what else to do. They’re out there.”
“Who is, sweetheart?”
You pressed your hand to your forehead, trying to settle your pulse because somehow the pet name managed to both make your heart dance and swell all at once as you gasped for breath, “The photographers. I saw the flashes through the windows, and I just—I can’t breathe, I can’t—”
“Hey, hey,” he cut in gently, all the casual charm draining from his voice. “You’re okay. Just tell me where you are.”
Your hands were shaking as you wiped your nose on the back of your sleeve, mascara smudging under your eyes. “It’s the first floor. Women’s bathroom, just past the elevators.”
“I’m coming to get you,” he said, firm but kind. You could hear papers shuffling around in the background. “Stay right there, okay? Lock the door, I’ll be there.”
You nodded, even though he couldn’t see it. “Okay,” you whispered.
The line went quiet. You stared at the screen for a moment after the call ended, the silence in the room pressing in again.
By the time you heard the knock, your breathing had evened out, though your hands still trembled faintly in your lap. You blinked at the handle, fingers curled against the hem of your skirt, heart still lurching in your chest. Another knock, so soft and careful, and you stood on legs that didn’t quite feel like yours.
You cracked the door open, and Harry stood there, suit jacket left behind, hair perfectly styled but tie loosened like he’d come in a rush. His expression was all concern, brow furrowed, lips parted like he was about to say something. But instead of speaking, he just opened his arms.
And you stepped into them.
He smelled like cedar and something warmer—amber, maybe, or vetiver—something expensive and clean. How many different colognes did this man own? His arms wrapped securely around you, pulling you in with that careful kind of pressure that told you he wasn’t going to ask you to talk, or apologize, or explain anything just yet. You let your head fall against his chest, the thrum of his heart steady beneath your cheek, and let out a shaky breath.
“I think I had a panic attack,” you whispered.
“Yeah,” he said gently, brushing a hand across the back of your hair. “I’m glad you called me.”
You swallowed, pulling back, stepping away from him and swiping under your eyes again with the pads of your fingers. “Sorry. I didn’t know who else—” You bit your lip, shook your head. “I just couldn’t go out there again. I saw all the flashing and…I just couldn’t.”
Harry’s voice was calm, reassuring. “Come on, I'll get you home. We don’t have to go out the front.”
You blinked up at him.
“I know a way out the back,” he said, giving you a quiet, coaxing smile. “Come on.”
“But don’t you have to get back to work?” you asked, voice still scratchy from the tears.
He gave a little shrug, the corner of his mouth quirking with something light and easy. “I’m the boss. I do what I want.”
You let out the faintest laugh, breath catching in a hiccup, and nodded. Then his hand found yours, and you let him lead you.
Chapter 4: Off the Record
Summary:
You spend a quiet evening with Harry, sharing takeout and half a bottle of wine on his leather couch, the city quiet behind glass. No cameras, no script, just quiet conversation and a strange, unexpected warmth that lingers long after you leave.
Notes:
(See the end of the chapter for notes.)
Chapter Text
The door to the sleek black Mercedes closed with a soft, final thud, sealing you into the cool, leather-scented hush of the cabin. You sank into the butter-smooth seat, your skin still damp from the bathroom panic, the fluorescent buzz still throbbing faintly in your temples. Your pulse hadn’t quite settled, still rabbiting under your skin. A moment later, the driver’s side opened, and Harry slid in beside you, calm as ever in his tailored charcoal pants, his jacket long gone back at the office, the pushed up fabric of his button up brushing the console as he checked his watch.
You stared down at your knees, only half-aware of the luxury wrapped around you in the clean stitching of leather, the faint smell of cedar and citrus that clung to the car’s air vents like aftershave.
“You… drive yourself to work?” you asked quietly, willing your mind to think of anything but what Gossip Girl might be saying right now. Your fingers fussed with the hem of your skirt, knotting and unknotting the fabric.
Harry leaned forward with a deep and unbothered inhale, turning the key. The engine purred to life like a tamed animal.
“No,” he said, glancing at you, his voice low and easy. “Not typically. But it’s always here for emergencies.”
You looked at him, biting your lip. “Like this?”
“Exactly like this,” he said, putting the car into reverse, one hand on the wheel, the other braced behind your headrest as he checked the back window. You let your eyes watch him, his chest open and turned slightly towards you, a peek of dark hair visible beneath his collar as he turned.
“I—I’m sorry,” you murmured.
“No need to be. I was glad to get out of that awful meeting.” His tone softened the blow of your embarrassment, always so gentle and understanding.
You opened your mouth, closed it, then tried again. “I should’ve called Blair again or—”
“Hey.” His voice cut in, quiet but firm. He stopped, stepping on the brake and looking over at you, his hand still clutching your seat with the car reverse, but he paused until you looked up at him.
“It’s really okay,” he said again, “I’m happy to take you home.”
You tried to speak, but your throat suddenly itched, thick with the pressure of too many feelings crammed into too small a space. You felt it creeping back in, that mortification, that edge of panic returning like a tide.
“I…” You swallowed. “I don’t think I can face my mom right now. After that.”
His expression shifted just slightly, brows softening. His hand left your headrest as he shifting into drive, and began pulling out of the garage. “The interview?”
You nodded, biting at your lip again, eyes falling back to the window as the car moved smoothly into the afternoon traffic. Outside, the city blurred with a sharp glint of sun on glass and the greens of Central Park. Everything looked too bright, like someone had cranked up the exposure. Harry didn’t push for more details on the interview, didn’t even ask what had made you call him, only began driving down the long, busy streets in that stoic silence he carried so well.
As the numbered streets began to descend, your heart tripped. “Where are we going?”
Harry kept his eyes on the road, one hand relaxed on the wheel. “You said you didn’t want to go home. Would you be comfortable going to mine?”
You blinked, surprised. The buildings outside began to shift—sleeker now, more residential, the edges of Greenwich Village coming into view.
“Oh…”
“I can turn us around, if you’d prefer,” he said, pausing at a red light. The sun poured through the windshield in golden ribbons, catching the edge of his jaw and the watch glinting at his wrist. “I just figured we didn’t need more cameras in our faces today. I live down in Tribeca, much more private.”
You exhaled slowly. “That...sounds nice. Thank you.”
He nodded, making the next turn downtown.
You sat with it for a moment, then blurted, “Really though, I don’t want to be a burden. I can text Chuck, or maybe Serena’s free, or—”
Harry glanced over, and you were surprised to see a smile on his face, warm and amused. “I think you’re nervous.”
“Am not!” you said instantly, cheeks heating.
He arched an eyebrow at you from his seat, “Then what is it?”
You huffed, arms crossing over your chest. “I just don’t want to impose, Harry. My god.”
“You’re not,” he said as if it had never even crossed his mind. “I invited you, quite the opposite of imposing.”
You glanced over at him, at the calm in his profile, the unshakeable way he navigated both the street and your unraveling.
You had to admit—he made it all feel a little less unbearable. Maybe not perfect. But bearable.
And the rest of the drive unfolded in a shared quiet, the kind that felt more like understanding than avoidance. You curled against the window, the city passing by in washed-out streaks of motion and light. Harry just drove, one hand resting easy on the wheel, guiding you down through the narrowing streets toward the southern tip of Manhattan like he already knew where you needed to land.
By the time the car came to a gentle stop in front of a towering brick building in his neighborhood, you were no less drained, but something in your chest had settled. Your limbs ached in that way they did after crying, your stomach hollow and weightless from forgetting to eat, your mouth dry and your head heavy. Still, when he came around to open your door and offer a hand, you took it.
Harry led you inside wordlessly, his presence quiet but altogether comforting. The doorman greeted him with a nod, and soon you were gliding into the elevator, watching as he punched in a code that made the numbers flash yellow before it began its ascent.
The air changed immediately as the doors opened soundlessly. It wasn't a lobby or a long hallway, but directly into a gorgeous foyer. Warm, still, faintly scented with cinnamon bark and something deeper—cedarwood, maybe, or the kind of musk that clings to a man’s favorite jacket. It was stunning and inviting and comforting all at once.
A long hallway stretched out ahead, painted in a rich, chocolate dipped gray. Warm gold sconces lined the walls, casting soft light over dark wood floors that gleamed beneath your heels. Framed prints hung in elegant intervals, some sharp cityscapes in black and white, others more abstract, curated but not pretentious. Everything felt intentional. So masculine and quiet and breathtaking. It wasn’t sterile like every other bachelor’s penthouse you’d seen whether in magazines or parties, this felt lived in and rich in texture and life. It was exactly as you’d pictured for a man like Harry.
He led you past the living space, the kind of room that could’ve easily belonged in a magazine spread, and into the kitchen. It was sleek but lived in. A wine bottle half-opened on the counter, a small bowl of lemons by the sink. You weren’t sure why that detail made you feel even more at ease. The space felt lived in, comfortable. A home, not just a house.
He gestured for one of the barstools at the counter, “Sit,” he said quietly.
You did, letting your bag slide from your shoulder with a soft thud. He handed you a tall glass of water and you took it with tired fingers.
“Thank you,” you murmured, realizing how parched you’d been from crying, and gulping down a few swigs right away.
“You’re welcome,” he replied, still watching you carefully, leaning on his forearms against the counter. “Do you…want to talk about it?”
You sighed, swallowing the last sip of water.
“The interview was just…awful.”
He grimaced politely, but let you continue.
“She made me feel like such a stupid little girl.” you said, picking at the skin of your fingers, “I don’t know what I was thinking, taking that interview, trying for that job. I have no experience, nothing to my name except the fact that everyone seems to know it. But I’m nobody. I’ve done nothing with my life.”
“That’s not true.”
“Partying and being on TMZ do not count, unfortunately.”
“What did you go to school for?” he asked softly.
“Business.” you sighed, “Minored in fashion.”
“That’s something more than half the people your age come in with.”
You shrugged, still not looking up at him.
“Are you hungry?” he asked.
You glanced up, “It’s okay, I’ll just…I can head back, grab something quickly on my way.”
He shook his head, “You’re already here, I’ll order something.”
“No, really, Harry, it’s okay,”
But he held up his hand, already reaching for a drawer with a chinese food menu on it, sliding it to you, “Anything you want.”
You managed a small smile and reached for the menu. But then the question slipped out, too fast for you to take it back.
“Do you have any chocolate?”
He looked up at you, a small, amused expression curling at the corner of his mouth. “Chocolate?”
You shrugged, a little bashful. “It helps me relax.”
“No dinner, no wine,” he said, turning on his heel to look back at the kitchen, “but chocolate is the great savior?”
“Guilty,” you said, softer now.
“Might have something here,” he murmured, rummaging into his tall dark wooden cabinets. Then, with a small sound of triumph, he pulled out a sleek bar wrapped in gold foil and held it up. “Dark, Swiss, and seventy percent. Does that work?”
You blinked, surprised, then gave a quiet laugh. “That’s… honestly perfect.”
He walked it over like it was something rare and sacred, but as your hand reached out, he swiped it back playfully, “Then that’s dessert.”
You looked up at him, the smallest smile twitching on your lips.
“We’re still ordering dinner,” he added, tapping the menu with two fingers. “Non-negotiable.”
And so, an hour later, you were curled up on the deep oak-brown couch in Harry’s living room, your heels long been kicked off, toes buried in the plush of the rug. The coffee table in front of you was cluttered with opened white takeout boxes, little red symbols steaming faintly as you picked through lo mein and shrimp dumplings with a pair of chopsticks.
Harry sat nearby, not quite on top of you, but close enough that his knee occasionally brushed your thigh when he leaned forward to dish out more beef with broccoli. He’d shed his business attire for his comfier home clothes, a nice black tee shirt with loungewear sweatpants. He’d offered you the same, but you turned him down, sticking with your business attire. Part of you was afraid to smell like him, to have to…give back his clothes. You watched him, here, in the comfort of his home, out of the usual hustle of the world you both inhabited. He seemed so…normal here.
The city glowed outside his windows, soft and golden, the sun beginning to dip behind the buildings. Jazz played faintly from the built-in speakers, slow and low and smoky, barely loud enough to make out the notes.
You swallowed your bite, pointed at him with your chopsticks. “Okay, one more time. You’re in what kind of finance?”
He smiled a little, having been the third time he’s tried to explain his business, setting his container down with a quiet clatter. “Private equity.”
You squinted. “Still means absolutely nothing to me.”
Harry chuckled, reaching for his glass. “It’s boring, really,” he said, shrugging. “We buy companies, fix them up, and try to sell them for a profit. That’s the simplified version.”
“And you like that?” you asked, eyebrows raised as you reached for another dumpling. “You like…fixing companies?”
He smiled faintly. “Not really,” he admitted, leaning back into the cushions. “But it’s the family business. My mother started the firm and my father joined her. My brother’s there too.”
“If you don’t like it…why keep doing it?”
His gaze met yours, thoughtful. “I suppose that’s a fair question,” he said, lifting the wineglass and rolling it once in his fingers before taking a sip. “I’ve never really let myself think about doing anything else.”
You leaned back too, mirroring him, your head resting against the cushion. The leather was cool against your temple. “But if you could,” you said gently. “If you could do anything in the world… what would it be?”
There was no dramatic shift in his expression, no overt tell, but something in him stilled. Like the question had reached a place he rarely visited. He set his glass down with care, his fingers tapping once against the rim before leaning back again.
“I don’t know,” he said finally. “When I was a kid, I wanted to be a jockey.”
You blinked, caught off guard, then laughed. “Like… for racehorses?”
He gave you a sheepish grin and nodded once.
“You’re a bit tall for that now,” you teased, grinning. It softened the air between you. He only smirked and reached for the chocolate bar, unwrapping it slowly.
He broke off a square and held out the rest to you between two fingers, his gaze a little more curious now. “What about you?”
You accepted the bar, the glossy chocolate warm from his touch. “We’re not talking about me.”
“Why not?”
“Because I came here in crisis and ate about fifty dollars worth of Chinese food.”
He smiled, watching you. “You’re deflecting.”
“I’m processing.”
Harry laughed at that, low and surprised, and took a bite of the candy he’d snapped off for himself.
“Processing, then." he said with his mouth full, "But you still owe me an answer someday.”
You glanced down at the bar, fingers smoothing over the foil where it peeked through the paper sleeve. It was some fancy Swiss brand you couldn’t pronounce—elegant, understated, and clearly expensive. You peeled it open slowly, letting the crinkle of the foil fill the quiet between you.
“Besides,” you said, taking a bite. The chocolate melted the moment it hit your tongue. Silky and rich, with a depth that made your shoulders drop, a full-body exhale in confection form before you continued, “You never answered me the other day, and it’s been bugging me.”
His brow furrowed slightly. “What’d I miss?”
“I asked if you’d ever been in love.”
You took another bite, slower this time, letting the taste linger. You looked at him over the edge of the wrapper, eyes curious but steady, a little cheeky still, but quieter now too. Something about the silence of his apartment, the softened light catching in his wine glass, made the question feel different this time.
He didn’t answer right away. Instead, he pressed his lips together, eyes shifting away as he reached for his wine glass again, stealing time as his fingers wrapped around it with an almost practiced calm. He swirled the deep red thoughtfully, brought it to his lips, then said, “Have you?”
You nodded once.
“Tell me,” he said softly, his voice echoing in the glass a bit and finally taking a long sip.
A smile tugged at the corner of your mouth, your gaze dropping back to the chocolate in your hand, though your mind had already drifted far from the present. “Nate Archibald.”
Harry nodded like he recognized it from a headline or a cocktail party conversation. “I know that name.”
“As you should,” you replied, tilting your chin up in mock pride. “The man’s going to be running for mayor someday.”
“We need a young mayor,” he said, humoring you.
“I tend to agree,” you murmured, the smile fading into something softer, sadder maybe.
A long pause stretched between you, filled only by the distant sound of traffic somewhere far below. You felt Harry’s gaze land on you again, all warmth and thoughtfulness, still tasting of red wine and quiet interest.
“So,” he said, voice low, “tell me about it.”
You smiled, a little crooked, a little ironic. “It’s the best kind of story,” you said softly. “Young and dumb and facing the wrath of Gossip Girl day in and day out.”
Harry huffed a little laugh, but let you continue.
You reached for your wine glass then too, hands wrapping around the base of the glass as you settled deeper into the couch. The takeout was forgotten, cold by now, but the wine was smooth and dark and grounding in your hand.
“We stayed together through college,” you said, your gaze focused somewhere inside the swirl of red in your glass. “He was so kind, so thoughtful. He’s the sort of person who makes you feel like things might actually be okay, even when everything else was chaos. He never cared about Gossip Girl or that I showed up on the cover of magazines after we’d been out for the night.”
You glanced up, catching Harry’s eyes briefly before looking away again. “But then I... I got caught up in everything. The parties, more TMZ headlines. I was still trying to figure out who I was, and Nate already knew who he wanted to be. We just sort of... grew in different directions.”
You paused, then added with a softer smile, “No screaming matches or scandals. Just time doing what time does best, I guess. We grew apart.”
For a moment, there was only the low hum of the city far below, the quiet sipping of Harry drinking from his glass.
“That kind of ending,” he said finally, swallowing, “can hurt in a different way.”
You nodded slowly, sighing out a quiet, “Yeah.” Your gaze dropped again, fingers tracing the rim of your glass, but something pulled you back. You looked up, caught the way the amber light hit his face just so.
“But you don’t get to get away with not answering,” you said, a touch of teasing cutting through the softness. “I told you mine.”
His lips twitched, just slightly. Not quite a smile as he looked at you for a moment too long before speaking, as if weighing the cost of his honesty.
“Nothing worth retelling,” he said finally, voice low, brushing a thumb across the base of his wine glass. “I’ve dated a few women, especially when I was younger, but…just infatuations.”
You tilted your head, watching him closely.
Harry exhaled, slow and shallow, before leaning back into the couch. “I've always found it so...difficult,” he admitted, his eyes still trained on the glass in his hand. “Love. Or... whatever it is people mean when they say that word.”
There was no bitterness in his tone, only the quiet sort of defeat, like he’d long accepted this part of himself as fixed.
“I feel like a child when I think about it. Foolish. Like there’s something I missed somewhere along the way.” His voice cracked at the edges, just barely. “I watch other people do it so easily. Fall in and out, move on, start again. And I just... don’t. I can’t.”
You watched him as you asked, “So... when you’re in relationships?”
He gave a dry little laugh, almost at himself, eyes flicking to the glass in his hand before setting it aside. “I haven’t had anything serious in a long time.”
He paused, lips pressing together for a moment, fingers twitching along the armrest of the couch. “It’s not like I avoid them or have a laundry list of things that a woman needs to have. I think I just... hoped it would click at some point. That it’d feel easy, natural.” He shook his head lightly. “But it never did. Not for me.”
You couldn't help but just watch him still, your eyes tracing the profile of his face in the dim light.
“I guess that’s part of why I said yes to Adore,” he went on. “It was a shortcut, wasn’t it? The idea of something... tidy. Packaged together to ‘check my boxes’ as they always put it.” His brows furrowed slightly. “I think I was hoping someone would just show me how to do it. Or that maybe I’d finally feel something I was supposed to feel.”
You tilted your head slightly. “The way you talk about it… it kind of sounds like a business transaction.”
“That’s all I know how to do,” he said quietly. “Negotiate. Analyze. Look for risk.” A faint smile tugged at his mouth, though it didn’t reach his eyes. “Isn’t that what marriage is? Looking for the right assets in someone else that match yours, hoping it’s someone you can tolerate?”
You didn’t speak. You just eyed him as the last of the light dipped low over the skyline beyond the window, casting the room in honeyed gold and soft gray.
He exhaled slowly, like something in his chest had unclenched. “It’s stupid,” he murmured, voice low now. “But sometimes I think... maybe it’s just not in me.”
The silence that followed didn’t feel uncomfortable. It was something quieter. Shared. Heavy, but not unbearable.
You shifted your gaze down to the chocolate bar resting between you on the couch, then leaned back into the cushions, your voice nearly a whisper. “I don’t think that’s true.”
And neither of you said anything after that. It wasn't for a little while, until you spoke again.
“It’s odd, isn’t it?” you murmured, almost to yourself.
Harry’s gaze drifted toward you, soft and unreadable in the fading light. His eyes found yours, and held.
You hesitated, looking at him for a moment, studying him. The way the golden evening halo framed the line of his jaw, the way his eyes always looked so much warmer when he wasn’t thinking too hard about what to say.
“I never really talked to you before,” you went on, slower now. “I mean, why would we, right? But now… I think I like you more than the whole rest of our stupid world.”
Something flickered across his face, like the beginnings of a smile, small and wry. “And what world is that?”
You tilted your head, still looking at him. “The vapid. The superficial. The people who mistake cruelty for intelligence.” You said it like a confession, like maybe you were afraid he’d disagree.
But he didn’t. He just watched you right back, eyes steady.
“You’ve been here this whole time,” you added softly, “so good and earnest. So kind. I would’ve never guessed.”
His smile didn’t deepen, but his eyes did. “Are you saying you’re glad to finally know the real me?”
You didn’t answer at first. You were too busy studying him again. The way he didn’t look away this time. How he watched you like he wanted to memorize the exact shade of your expression. Like maybe the silence between you was saying more than the words ever could.
Your throat tightened a little. You nodded. “I think so.”
And he nodded too, quiet but certain. “I’m glad to know you too.”
It was odd. How easy it had been. How… natural, with Harry. Without the cameras, the curated photo ops, or whispers of Gossip Girl in the back of your mind. And it’s not like there was some grand shift in things, no movie-scene moment to mark what changed. Just quiet conversation in a quiet penthouse, over warm food and warmer company.
The strangest part was that you’d known Harry practically your whole life. Two decades of charity galas and Christmas parties, summers in the Hamptons and fundraisers, all blurring together into polite nods and passing familiarity. And yet, somehow, you’d never really seen him. You wondered if he’d ever really seen you either.
And maybe that was what threw you. Because you knew what this was. You just had to keep reminding yourself. It was a business arrangement. Fabricated and curated at every angle, meant to redirect attention, control a narrative, give both of you something to gain. A clean exchange. Attention for protection. Proximity for peace of mind. It wasn’t love or even dating, really. It was strategy.
But Harry… somehow made it feel less like a performance or something to endure. Even knowing the script, he delivered his lines with warmth and care. He showed up when you needed someone most, a quiet life raft in the storm of flashbulbs and gossip columns.
He was kind, yes, but not the kind you’d learned to distrust. It wasn’t superficial or transactional. You knew the type, some saccharine sweetness to get something in return. No, this was different and disarming. The kind of kindness that made you wonder if maybe, beneath it all, he did care, just a little, about how you came out of this. About who you were in it.
“Are you even listening?”
Your eyes snapped up, pulled back to reality, your fingers still clutched around a soft blush cashmere top marked final sale in the far corner of Saks.
“Sorry, B,” you sighed, “Just... distracted.”
Blair rolled her eyes dramatically, her glossy curls bouncing with the motion. She flipped a sundress over her arm and glanced at you with a perfectly arched brow. “Yeah, I’ve noticed. And why are you browsing the sale section like some peasant?”
You let go of the sweater, smirking faintly. “Still don’t have access to my accounts, remember?”
“Not even store credit?” she asked, batting her eyes, wide and confused.
“Nope.” you said with a pop of your mouth. She huffed out a breath of air, exasperated as she took another garment from the racks.
Her eyes peered over at you, softening, “I'm sorry, that's awful. I just forgot.”
You shook your head, already forgiven.
“Can we talk about whatever it is that’s going on with you?” she asked, voice more casual but eyes sharply averted, scanning a buttery yellow slip dress in her hands.
“Like I said,” you murmured, fingers brushing through the silk and cotton, hangers clicking softly, “just… stuff. A lot of it.”
“So you’re just not gonna tell me?” Blair asked, arching a brow, eyes still averted from you.
You glanced at her, and something in you tugged. You knew she was trying, in her own Blair Waldorf way. But still. “Why, do you wanna tell me what’s been going on with you and Chuck?”
That made her pause. She made a face, wrinkling her nose like she’d smelled something sour, and turned to rifle through another rack. “We’re back together,” she said vaguely, “for now.”
“I can almost hear the wedding bells,” you swooned.
She gave you a dry little glare, but the corners of her mouth twitched. “I hate you.”
You blew her a little kiss with a wink.
A little quiet settled between you. Something gentle and familiar in the way only years of knowing someone inside and out could have. And the quiet you could only earn through time. You didn’t have to fill it when it came to Blair.
“So,” she said after a while, tilting her head, “do you, like, drive yourself around now?”
You looked at her. “What?”
“I just meant… since your dad took away your driver. You know, I read somewhere that walking helps clear your head. It’s apparently very meditative.”
You scoffed, “Oh, totally. Just me and my inner peace, strolling through the Upper East Side while I try not to cry about how I don’t know how to get a job or fill out a rental application.”
She grinned. “You could always—”
“Don’t.”
“—take the subway.”
You both froze, eyes meeting over the metal racks.
And then the air cracked, a sputter of a laugh escaping your mouth before you could catch it, and Blair, ever the actress, tried to stifle hers with the back of her hand. It only made it worse. You doubled over slightly, your fingers digging into a rack of overpriced linen as the laughter kept coming, harder now, breathless and stupid.
Blair was laughing too, trying to talk through it. “You should’ve—your face—when I said it—”
“God,” you said, covering your face. “We’re such assholes.”
She grinned, victorious. “Maybe, but least I’m a well-dressed one.”
You nudged her with an elbow, still smiling, and for the first time in forever, it didn’t feel like a performance. Just two girls laughing in a store they’d grown up in, slipping into an old rhythm without trying.
And somewhere in the back of your mind, you realized you handn't even checked your phone in hours. It hadn’t buzzed. It hadn’t lit up with alerts or updates or Gossip Girl headlines.
For once, the world hadn’t asked anything of you.
“Well, would you look at that. You two haven’t changed a bit.”
The voice was familiar. It sounded warm like like post-lecture coffee runs and sunlit walks, dipped in something boyish and nostalgic.
You turned, already knowing who it was before your eyes found him.
He stood there in a white polo and relaxed chinos, tan from the kind of sun you only get on rooftops and sailboats. His grin was easy, boyish as ever. His eyes caught yours like a breeze in spring, familiar and a little too lovely for your own good.
Your mouth parted.
“Nate?”
Notes:
last notes: guyssss, im sorry if this chapter is a little lackluster. I feel like im facing the barrel of an awful writer's block. I have so much planned for this story but when I sit down to do anything I just completely blank!! so please bear with me for the time being and thank you for reading!!! your kind words literally turn my day around, so any thoughts are appreciated!!
Chapter 5: Clause and Effect
Summary:
Summary: You spend a sunny afternoon with Nate, slipping easily into old habits and laughter that feels too good to question. When you reach out to Harry the next morning, it’s cold and all business—a sharp contrast to the time you’d shared just days before.
Chapter Text
Blair hadn’t exactly suggested that you go with Nate when he asked to talk with you. No, she had practically shoved you out of the Saks on Fifth Avenue. And when you’d flashed your eyes over your shoulder at her hard push out the door, you’d seen her smirking as she said she’d call you later for details.
And maybe you should’ve resisted, maybe you’d thought about it, meant to tell him that you couldn’t, shouldn't, but then Nate looked at you with that summer-in-the-Hamptons boyish grin and said “Want to walk?” and your body betrayed your better judgement before your mind could catch up.
Now here you were, two blocks later and a green tea in hand next to a boy from your past.
The city had softened in the afternoon light, something slower and charming about this pocket of the Upper East Side. The sun filtered gold through the budding sycamores, the street noise reduced to the occasional car horn or distant bark. In the little triangle park you wandered into, the grass had just been cut, releasing the sweet green scent of spring into the warm air. Tulips lined the edge of the lawn, yellow and blush pink, reaching lazily toward the sky.
You stole a glance at him over your coffee lid. His hair was a little shorter now, a little more kept. The sleeves of his white polo were pushed up just enough to show the tan from the early spring boat rides with his mother, a tradition you wondered if they still shared.
“So, tell me, have your ears been ringing?” you asked, turning toward him with a teasing smile.
He blinked, then grinned. “Should they be?”
“I was just telling someone about you last night.”
“You’re making me nervous now,” he said with a smile, sipping his Americano.
You shook your head, licking the remains of tea from your lip, “No, no. Always good things. I couldn’t imagine anyone saying a single negative thing about you, Archibald.”
“Mm. I feel like you’ve got plenty of dirt on me, Montclair.”
You smiled despite yourself. Dammit if that cheeky smile didn’t make your stomach somersault.
“What have you been up to?” you asked, dragging your eyes away from his.
He ran a hand through his sun-lightened hair, shrugging. “Trying to get my foot in the door with the governor’s office. I’ve been meeting with the current mayor, doing all the typical schmoozy, mayoral handshake things before my name can get anywhere near a ballot. My assistant thinks I should start fundraising.”
“Fundraising?” You raised a brow. His family was one of New York's wealthiest, after all. “You?”
“More like... collecting favors. Gaining support,” he said, giving you a cocky little smirk.
You snorted. “Of course. Good ol’ money politics.”
“I prefer to call it strategic networking.”
“Well, I’ll spread the good word.”
“I’d appreciate it.”
He slowed then, and you felt the shift in his body language, the way he angled toward you, the way his eyes found yours with just a hint too much stillness.
Around you, the breeze tugged at the hem of your skirt. A couple on bicycles passed by with their music blaring. A pigeon fluttered into the low branches overhead. You could feel the city humming around you, and still, it was like the noise dropped away.
“What happened to us?” he asked quietly.
Your breath caught, your hand tightening around the paper cup. “I—what?”
“You and me,” he said, stepping closer. “We were good, weren’t we?”
“Yeah but…Nate, don’t you remember? You were so focused on becoming the next president of the United States one day, and I… well, I was busy partying and... not doing anything at all. Actually, I think your exact words were: You lack the ambition I need in a partner.”
He grimaced like you’d smacked him. “Jesus. See? Told you you’d have some dirt on me.”
“I hardly think honesty counts as dirt. You were right. You probably still are.”
“I don’t think so,” he said, voice low.
Your pulse flickered.
“Okay,” you said, biting your lip. You looked away, pretending to focus on the nearby tulips, but your mind was a minefield. Harry’s face flashed across it — chocolate brown eyes that were like molasses and sugar, his hands, his lips on yours. And the damn lie that held you together, this fake relationship stitched out of spite and image control and damage management.
And now here was Nate, so easy going and kind, looking at you like he meant every word.
His hands came up suddenly, settling at the bends of your elbows, and his touch was warm and all too familiar. A little too tender.
“Can I take you out sometime? Like old times.” he asked.
“I…”
Your chest tightened. Should you tell him the truth? That you were seeing Harry, that it wasn’t anything real, that you’d love to see him again, to try again. Should you tell him you were a wreck in last season’s clothing, pretending not to unravel under the weight of your parents’ disappointment? That maybe you weren’t the girl worth taking out anymore?
But instead, you smiled, soft and unsure. “Yeah. Maybe.”
He smiled like that was all he needed. Like it was everything, and he pulled you into a hug.
You didn’t resist as your arms wrapped around his neck, and his around your waist, and you felt him breathe you in.
“You still wear Chanel?” he murmured against your hair.
You pulled back to look up at him. “You remember?”
“Gave it to you every Christmas, didn’t I?”
Your heart thudded and you nodded. Your eyes searched his face, the boyish gleam in his expression, the dimple in his left cheek, the thick lashes that framed his too-blue eyes. And in that moment, it almost felt easy again.
A sudden hiss broke the quiet.
You barely had time to register the sound before a fine mist caught your ankle, a cold spatter against your calf. And then, like some cruel twist of fate, a full arc of water burst from the lawn beside you, catching the breeze just enough to spray across your bare legs and your entire skirt.
You yelped, stumbling back with a high-pitched squeal, your hands lifting instinctively. “Oh my god! Not my Valentino—!”
The words were screeching and panicked as you danced out of the sprinkler’s reach, clutching your skirt to keep it from danger. Your shoes were already darkening, delicate satin turning damp in spots.
Nate was doubled over, hands on his knees, howling with laughter like this was the funniest thing he’d seen in weeks. “Oh no,” he gasped through breathless laughter, “the horror! Whatever will you do, princess?”
You glared at him, though you could feel your own laughter threatening to break through — bubbling up in your chest, effervescent and sharp.
Without thinking, you stepped back toward him, grabbing his wrist and spun him, with surprising force and strength, straight into the sprinkler’s spray.
You woke to warm light spilling through the soft pink curtains and the gauzy canopy above your bed, the morning sun casting delicate patterns across your sheets. For once, it felt like the light belonged there, all gentle and golden— unbothered. You stretched slowly, smiling to yourself, the memory of yesterday still humming somewhere beneath your skin.
Reaching for your phone, you scrolled absently, surprised to find your notifications empty. No missed calls, not even a Gossip Girl ping.
How uncharacteristically quiet.
Maybe it was time to change that.
Harry hadn’t arrived by the time you got to Ladurée later that morning. So you chose a table outside, one perfectly positioned in the sunshine, just enough to warm your bare shoulders and for anyone passing by to notice you and snap their photos.
You ordered two sparkling waters, his espresso, your latte and proceeded to scroll absently through your phone. Time passed in loops, watching the people drift past in pressed trousers and their work attire, dogs and shopping bags and quiet conversations weaving together like a hum.
You didn’t look up until the light shifted with a shadow casting long across the iron chateau table. You felt the tension in the air, low and tight like an impending storm cloud.
“Oh,” you said, startled. “Hi. Sit, I think this is a good spot for—”
“We need to sit inside.”
Your brows lifted. Harry didn’t meet your eyes. There was a tick in his jaw and unfamiliar scowl carved deep between his brows, as if it had settled there overnight.
“O-okay…” you said, rising carefully, phone in hand. You signaled the waitress you’d be moving and followed him wordlessly into the quiet interior. The back table he chose was tucked in shadow, far from the sunlight, far from the onlookers you thought you were trying to grab the attention of.
The patisserie inside was tasteful. Mosaic tables, floral wallpaper, soft pinks and ivories in curved crown molding. It was elegant and soft and inviting. But nothing about Harry was soft today.
He dropped into his seat with a heavy sigh.
You sat too, quietly. “Is everything okay?” you asked as the waitress placed your drinks in front of you. “I got you coffee,” you added, almost as an afterthought.
Harry gave a short nod, barely even a grunt passing his lips in thanks. Instead, he set a leather briefcase down beside him and unlatched it with a sharp flick. From it, he drew out a few sheets of paper — and then one thicker object, glossier, heavier. When he laid it on the table, your stomach dropped.
Your expression cracked before you could stop it. “Oh god—”
“What were you thinking?” Harry's voice was low, taut.
“I didn’t know anyone saw us, I—I’m so—”
“Sorry?” he cut in. “You don’t look like it. From the looks of it, you’re having the time of your life with him.”
You looked down, ashamed. Your fingers trembled slightly as you touched the edge of your cup.
“Are you not taking this seriously?” he asked. “Do you understand what this means for my family? For Camilla?”
You opened your mouth but couldn’t find the words. Your throat had closed up. You felt heat rising behind your eyes, something tight and sour pulsing at your temples. He was looking at you with something darker than anger. Something close to disappointment.
“I didn’t see anyone,” you said weakly. “I just…we were catching up, he came out of nowhere, wanted to talk. It wasn’t—”
You took a deep breath and swallowed. “I didn’t mean for Camilla to—”
“If you don’t want to do this anymore,” Harry cut in again, voice like stone, “if you want to run around town with your ex-boyfriend, that’s fine. But I’m not going to be part of it if that’s the case.”
You stared at him, stunned. Your voice rose a notch, defensive and tight. “You’re the one who asked for this, for front page news and–and—”
He didn’t blink. “Don’t misunderstand me, Miss Montclair. I don’t give a damn what they write about me.” He tapped the magazine cover like it disgusted him. “But you’ve made my family look foolish. You’ve given the press another reason to treat Camilla like a punchline. After everything I’ve done to get her out of it.”
He leaned back slowly, crossing his arms. His voice cooled even further, “Do you understand how that feels?”
You blinked at him, the words slicing too close. “What? Do I know how that feels? Harry, all I ever am is center stage. I don’t get the luxury of choosing when people look at me. I can’t escape it.”
His jaw flexed, but he didn’t break his stare.
“Seems to be exactly how you like it.”
You inhaled sharply, fury beginning to rise. “Are you serious? Fine. You don’t want this anymore? Cool, we can end it right here. Have a nice life, Harry.”
You pushed back your chair, the metal legs screeching slightly on the tile. You stood, wanting to walk, to vanish through the gilded doors, to disappear for once in your life without someone following, watching, reporting. You wanted just five minutes where the world didn’t have your name in its mouth.
But before you could take a step past him, his hand was on your arm. It wasn’t demanding or painful, but just a softness, his thick fingers wrapped around your forearm, bare skin on bare skin.
“Sit. Please. I’m sorry.”
You stared down at him, silent. And for a moment, you saw more than the ire beneath his eyes. You saw how tired he was, how melancholic he was underneath it all. It reminded you of just the other night, of the soft spoken words exchanged, when it was only the two of you, just four walls and two people who felt unseen by everyone around them.
You stood like that for a beat longer, torn between the fire still hot in your chest and something else rising up behind it. Then you sighed, lips pressed tight, and slid slowly back into your seat.
Harry exhaled too, but it didn’t ease the tension in his frame. He leaned back in his chair, jaw tight, arms folded as he stared off, away from you, toward some spot on the far wall like it might tell him what to say.
The silence stretched taut and uncomfortable, like the pause before a verdict.
Then finally, his voice, low and quiet: “I don’t want to end this.”
You paused. That wasn’t what you expected. Not after that performance. You tilted your head, still bristling. He finally looked at you again.
“Do you?” he asked, and the question echoed between you.
But you felt it, that weight of everything. Of Nate, the way his laugh still made something inside you flutter, like a reflex you hadn’t grown out of. You thought of how easy it would be to fall back into that old rhythm with him, comfortable and familiar. He was everything your parents wanted for you — shiny and clean and appropriate. With Nate, you could smooth your edges and no one would question it. They’d call you mature. They’d call you healed.
But it wouldn’t fix this. It wouldn’t undo the photo, or the headline, or the way Harry had looked at you when he dropped that magazine on the table. You’d humiliated him, you’d jeopardized Camilla’s well being by not thinking about the outcome of a simple stroll in the park with an ex boyfriend.
You owed it to Harry to not walk away when things got hard. And you weren’t about to give your parents the satisfaction of being right.
“No, I don’t,” you whispered, surrendering.
Harry’s eyes met yours. “Are you certain?”
He wasn’t condescending or sarcastic. He was just… asking. So gentle and soft spoken despite your expression of petulance. And you realized that it wasn’t something you often got. Someone asking what you wanted.
“Yes, I’m certain,” you said, a little more sharply than intended.
He nodded once, calm and settled. Like something in him had been exhaled. He moved the magazine aside, tucking it beneath a stack of printed pages.
“What is that?” you asked, eyeing the pile.
“I had my lawyer draft a contract.”
Your heart jumped. “A contract? Jesus, Harry!”
“This is serious, Miss Montclair. I thought we had an agreement. I can’t keep relying on good faith alone.”
He was revving you up on purpose, he had to be.
“Oh, you asshole.”
“It’s still entirely up to you,” he said coolly, ignoring your jab.
You stared at him, pulse quickening. “Can you just give me something? I can’t even tell where your head is anymore.”
“I want to protect my niece.”
You looked away, toward the street outside. Cars passed slowly. A woman pushed a stroller past the glass. Life moved on without you.
“I meant about me.” you said quietly.
Harry sighed, “Does it matter how I feel about you?”
You met his eyes again. “Yes.”
He leaned forward slowly, resting his elbows on the table between you, fingers clasped together, “I think we have great potential to change this around. But only if we’re on the same page about things.”
You ignored the fact that that was not, in fact, what you meant at all by your question.
“…Okay,” you murmured. “What does the contract say?”
He shuffled papers around before handing it to you.
“It outlines the rest of the time we have together. Up through the Hamptons trip. No other relationships, no going on other dates. And then logistical things, mostly. Lodging, transportation, your allowance.”
Your eyes snapped to his. “My what?”
He sighed. “There’s a credit card I opened for you. You’ll need it if you agree to continue.”
“This is insane. I don’t need your money.”
“On the contrary, you do.” he nodded, “Isn’t that partially why you’re doing this with me? Besides, there is…there’s one other clause.”
“Oh god. What now?”
“My mother wants to meet you.”
Your face froze. “Excuse me?”
“It’s your decision. But if you do sign, I’ve already arranged a stylist to help you prepare. Margot. I’ll give you her address, of course. She’ll take care of everything.”
“My clothes are fine,” you snapped, arms crossed.
“I don’t doubt that,” Harry said, voice gentler. “But my mother is… particular. Margot knows what she likes. Please. Just trust me.”
You looked at him then. Long and hard. He wasn’t smirking or playing. There was something tired in his eyes. Something cautious.
You sighed, then picked up your latte, sipping as you read through a few lines of the contract.
Both parties agree to maintain the appearance of a committed, exclusive relationship for the duration of the agreement. Neither Montclair nor Castillo shall engage in any romantic or sexual relationships with outside parties, nor participate in public behavior that would suggest otherwise.
Montclair agrees to meet with Mrs. Evelyn Castillo at her residence, located at 834 Fifth Avenue, New York, NY, on MAY 10TH at 12:00PM, for the purpose of establishing social rapport and satisfying familial expectations.
Montclair is granted access to a Castillo Holdings credit account for incidental and appearance-related expenses, not to exceed a total of $50,000 USD without prior written approval. Said funds shall be used solely in service of upholding the visual and social standards of the arrangement.
This agreement shall remain in effect through JUNE 20TH, concluding with the final appearance at the Montclair family’s summer estate in East Hampton during the WHITE PARTY FUNDRAISER FOR HENLEY’S YOUTH CENTER, unless terminated earlier by mutual consent or in response to a material breach.
You held the papers in your lap, scanning them with narrowed eyes. “So…what do you want from me?”
Harry frowned. “Excuse me?”
“When I meet your mother. How do you want me to act? Do we go full spoiled brat, or do I tone it down? Act like a proper young lady?”
He tilted his head slightly. “I… just be yourself, I suppose.”
You groaned. “Myself? You must not want to impress her much.”
“You’re being impossible.”
“I’m just asking a question, Harry.”
He sighed, pinching the bridge of his nose.
You stared at him for a beat. At the curve of his shoulders, drawn tight beneath that button-down. The dark smudge beneath his eyes from lack of sleep. Whatever this had cost you, it was clearly costing him, too.
You looked back down at the contract. The words blurred a little from how long you’d been staring at them. Your name printed in legal font. The terms of your worth itemized and assigned deadlines.
It should have made you feel small.
Instead, it made you feel… necessary. Like this was something only you could do.
You flipped the packet slowly, thumb pressed to the crease as you found the dotted line at the bottom.
“Do you have a pen?” you asked.
He looked up, blinking a few times. Instead of answering, he just reached into his blazer pocket and handed you a silver pen that was heavy and engraved with Castillo Investments. Probably custom. Of course it was.
You uncapped it, signed your name at the bottom without a flourish, and slid the papers back across the table toward him.
He took them with a nod, signing his own name.
Then, without saying anything, he pulled a sleek black card from his wallet — a Castillo Holdings AMEX — and set it gently beside your latte. A second later, he was pulling out two business cards to sit next to it.
“Here,” he said. “That’s Margot’s number. And my driver’s. He’ll be outside at eleven tomorrow for you.”
You took the card and pocketed the phone numbers, sliding them all into your purse.
The both of you sat in silence for a long moment.
“I… I really am sorry, Harry,” you said finally, your voice low. Honest.
He nodded mournfully, “I know.”
You looked down, fingers brushing the edge of your now-cold latte. “So when I meet your mother…” you hesitated, glancing up at him, “do you think she’ll like me?”
It was quiet for another long moment, then, for the first time all morning, Harry smiled. Just a small one, but it softened the edges of his face.
“You’ll know when you see her,” he said gently.
You gave a faint nod, lips twitching despite yourself.
“Thank you,” he added, voice quieter now. “For… continuing with the agreement.”
You looked over at him, held his gaze for a moment, and nodded.
Another pause settled between you, more comfortable this time.
“Well,” he exhaled, collecting his things, “I don't see a reason not to use this whole outing to our advantage, right?” he said finally, a slight lilt returning to his tone.
You raised an eyebrow, eager to lighten the mood again. “What exactly are you proposing?”
His mouth twitched. “A kiss goodbye?”
You gave him a look. “I’m starting to think you liked kissing me, Castillo.”
He chuckled a little, standing and tossing cash on the table. His hand found the small of your back as you moved to the door, firm and steady, guiding you outside.
“Don’t get so ahead of yourself, it’s only our second kiss,” he murmured, lips brushing close to your ear, and you had to force the blush away from your cheeks.
Outside, the city was buzzing again. A black car already idled at the curb, sleek and imposing with tinted windows. Harry opened the door and turned to you.
“For you,” he said, like it was nothing.
You blinked. “I—I wasn’t expecting—”
“You agreed,” he said, that subtle firmness shutting your mouth. But there was a glint in his eye now, something amused and warm.
Right, the newly signed contract. The terms, the conditions, the performance. The job you’d already nearly blown. You’d agreed to this, afterall.
You sighed, stepping between him and the open door. “Well… thank you.”
His voice dropped, suddenly all business, and his eyes flickered behind you and back to you. “We have an audience, Miss Montclair.”
You willed yourself not to look, but you could feel the invisible weight of a hundred eyes, phones angled, pretending not to watch. Gossip Girl working in real time.
This was why you came, anyway. The reason for meeting at the patisserie to begin with, wasn’t it? The photo op. The performance. You looked up at him, heart beating a little louder than you meant it to. You took a big breath before smiling up at him.
“I’m going to kiss you now, Harry,” you said softly.
His mouth twitched. “Why do you make it sound like a threat?”
Stepping in, you slid your hands beneath his blazer, grazing the fabric of his shirt, fingers brushing the buttons at the center of his chest. His arm came up, caging you gently to the ajar car door, and the city faded at the edges.
You leaned in, catching his lips with yours, soft, steady, practiced. You let your mouths meld together, long and slow and deep. You tilted your head a little, pushing up into him more.
But underneath the choreography, you were trying to say something else. That you were sorry. That you weren’t trying to humiliate him. That it must have felt like such a blindside, to wake up with his niece on the cover of the magazine, his own face, his own…what were you? Fake girlfriend? Making a fool of all of you.
You kissed him harder, bringing your hand up to his neck, pulling him in for more. His lips slanted to yours, his free hand going around your waist.
Look at me.
Look at us.
See how much I like him?
I’m sorry, Harry.
When you pulled away, it was only because you had to. Because if you didn’t, something might give. His hand lingered at your waist for half a second longer than necessary. His gaze found yours, steady and searching.
“Goodbye, Miss Montclair,” he said finally, voice low, rough around the edges, something unreadable curling beneath it.
“Bye,” you breathed, softer than you meant to, your body still humming with the contact, your mouth tingling from where he’d kissed you.
You slid into the car, the door closing behind you with a final, padded thud. The sudden quiet felt jarring, making your ears ring, like the air pressure had shifted. The tinted glass turned the world outside to shadow, and the cold leather pressed into your thighs, clashing against the warmth still blooming in your chest, your neck, the flushed skin below your collarbones.
Your phone was buzzing, and when you looked down, it felt like everything was falling back into place as it should.
Chapter 6: The Contract
Chapter Text
PERSONAL SERVICES & REPUTATIONAL STRATEGY AGREEMENT
This Agreement is entered into on MAY 8TH by and between:
- Harry Castillo, residing at Penthouse One, 56 Leonard Street, Tribeca, New York, NY (“Castillo”), and
- [REDACTED] Montclair, residing at 991 Madison Avenue, New York, NY (“Montclair”).
Collectively referred to herein as the "Parties."
RECITALS
WHEREAS, the Parties wish to engage in a mutually beneficial, exclusive, and public-facing romantic arrangement designed to enhance or protect reputational and familial interests;
WHEREAS, such arrangement shall remain confidential in its terms and maintain a consistent public image throughout its effective period;
NOW, THEREFORE, in consideration of the mutual covenants and conditions set forth herein, and other valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties agree as follows:
ARTICLE I – Relationship Expectations
A. The Parties shall present themselves as a romantically involved couple and maintain the appearance of exclusivity and mutual affection during public appearances.
B. Both Parties agree to abstain from engaging in romantic or sexual relationships with third parties throughout the term of this Agreement.
C. The Parties shall be required to make a minimum of one (1) public appearance together per calendar week, including but not limited to: charity galas, society functions, family obligations, or casual but conspicuous outings.
D. Public displays of affection (“PDA”) including but not limited to kissing and hand-holding are permissible and encouraged where appropriate. Any displays of affection beyond these (e.g., lap sitting, suggestive bodily contact, or other overt intimacy) shall only occur with the explicit and enthusiastic mutual consent of both Parties and should be pre-approved in advance of public display.
ARTICLE II – Confidentiality and Media Conduct
A. The Parties agree to uphold absolute discretion regarding the terms, scope, and nature of this Agreement.
B. No personal, contractual, or intimate details shall be disclosed to members of the press, social media, blog platforms, or any third parties, except where mandated by legal counsel or mutually agreed upon by the Parties.
C. Interviews given by either Party must be pre-approved in writing and shall not include sensitive details, emotional commentary, or personal speculation about the nature of the relationship. No intimate or private information is to be shared with members of the press or any external party.
D. The Parties further agree that no statements, implications, acknowledgments, or clarifications shall be made, directly or indirectly, regarding any internal family dynamics, past or present affiliations, or intra-familial relationships of either Party or any associated persons. This clause is intended to encompass all sensitive relational contexts that may arise, explicitly or implicitly, including but not limited to those relevant to the reputational management of certain family members whose privacy is of mutual strategic importance.
ARTICLE III – Required Appearances
A. The Parties shall appear together at the following mandatory events, unless otherwise excused by mutual written agreement:
(a.) The Hamptons White Party – June 15
(b.) The wedding of Serena Van Der Woodsen and Daniel Humphrey – Weekend of May 31st
(c.) Any events designated by the Castillo or Montclair families deemed materially relevant to the narrative or reputation of the Parties.
ARTICLE IV – Familial Obligations
A. Montclair agrees to attend a formal meeting with Mrs. Evelyn Castillo at her residence at 834 Fifth Avenue, New York, NY on May 10 at 1:00PM.
(a.) Montclair shall employ the styling services of Margot Loftland solely for the aforementioned meeting. Use of said stylist is not mandated for any other event.
ARTICLE V – Financial Arrangements
A. Castillo shall provide Montclair with access to a Castillo Holdings corporate credit account for use in fulfilling the visual and social expectations of this Agreement.
(a.) Account shall not exceed an aggregate spending limit of Fifty Thousand United States Dollars ($50,000 USD), unless prior written approval is granted.
(b.) Funds shall be used solely for event preparation, transportation, appearance upkeep, and related incidentals. Expenditures shall be subject to monthly review and audit by the Castillo estate manager.
ARTICLE VI – Transportation & Travel
A. The Parties agree to travel together when appearing at the same event, arriving and departing jointly, unless mutually agreed due to family obligations or logistical necessity.
B. Montclair shall have access to Castillo's authorized transportation services, including his personal driver and town car, for all appearances agreed upon under this Agreement and personal use.
ARTICLE VII – Term and Termination
A. This Agreement shall commence upon mutual execution and shall remain in effect through June 20, terminating upon conclusion of the Montclair family’s White Party Fundraiser for Henley’s Youth Center.
B. The Agreement may be terminated prior to its expiration upon mutual written consent or in the event of a material breach by either Party.
ARTICLE VIII – Emotional Disclosure Provision
A. In the unforeseen event that either Party experiences the development of sincere emotional attachment, romantic inclination, or any other affective deviation that compromises or exceeds the scope of this Agreement’s intended performance-based structure, said Party shall be obligated to initiate a private, in-person discussion with the other Party to disclose such development in full transparency.
B. The Parties shall, upon mutual verbal acknowledgment of said emotional complication, determine the appropriate course of action, including but not limited to termination, suspension, or revision of this Agreement. This will not be overseen by legal counsel.
C. No contractual penalties shall be incurred as a result of such emotional developments, provided the disclosure process is undertaken in good faith and in accordance with this provision.
D. Failure to disclose said developments in a timely and forthright manner may constitute a material breach, permitting immediate dissolution of the Agreement at the non-breaching Party’s discretion.
EXECUTION
IN WITNESS WHEREOF, the Parties have executed this Agreement as of the Effective Date written below.
Harry Castillo
Date: ____05/08_____
[REDACTED] Montclair
Date: __05/08__
Chapter 7: The Devil Wears Prada
Summary:
Meeting Harry’s mother was as intimidating as expected, with her cool poise and targeted questions. But you hadn’t expected her to reveal something about him that lodged itself in your mind and refused to leave, a quiet revelation that’s been wriggling there ever since.
Notes:
(See the end of the chapter for notes.)
Chapter Text
By the time Margot had finished all her poking and prodding, her tucking and smoothing and stepping back to assess, you were made entirely new, dressed like a diplomatic gesture. A polished little gift box tied up in celadon silk, stepping out of the grand building at half past the hour and headed for Fifth Avenue.
The dress moved like water when the breeze caught it, the hem brushing soft around your calves as you slid into the idling black car. The sheer green gloves were comforting in a strange way. Cool against your skin, whisper-light, embroidered in tiny loops that itched when you settled yourself inside the car.
Harry’s driver, George, you’d come to learn, closed the door behind you, the soft shutting silencing the city around you. Inside, the car was quiet and dim, the leather cool against your back. You glanced down at your shoes—pale taupe slingbacks, the kitten heel just high enough to be formal. The leather still held a faint gloss from where Margot had wiped them down before you left.
And as the car drove away from the curb, you watched the city go by. Buildings blurred, people hustled and you watched, distantly, wondering what was going on in each of their little lives. You still weren’t entirely sure of the point of all this. Meeting someone’s mother when you weren’t even dating felt a little silly. Besides, family made things complicated, more permanent. This, for all intents and purposes, was only a temporary agreement with an end date already in sight. June twentieth would come and go and things would…go back to normal. You’d return from your home in the Hamptons single and hopefully off the headlines for a while, and Harry would go back to his life with his niece safely tucked away at home.
Still, you thought, if Harry didn’t think it mattered, he wouldn’t have asked you. That had to mean something.
And you wondered, briefly, how many girls had made this same trip. How many had stepped out of a car, taken a deep breath, and prayed they’d be the one to impress Evelyn Castillo. Maybe none of them had. Maybe that was the point. Maybe no one was ever good enough for her son.
But before you could spiral further, the car slowed in front of a gray stone building. George came around to open your door.
“Good luck, Miss Montclair,” he said with a polite smile. You nodded in thanks, but your voice caught in your throat.
Before you could lift your hand to the buzzer—engraved in discreet serif: Evelyn and Harold Castillo—the door opened on its own. A man in a black tuxedo stepped forward.
“Miss Montclair,” he greeted, tone smooth, practiced. “Please, come in.”
Your kitten heels clicked lightly over polished cream marble as you followed him inside. The entryway was quiet, cathedral-high and filled with soft light. Molding curled across the ceiling like ribbon, and an arched staircase swept upward in graceful stone curves. Everything smelled faintly of peonies and linen and wealth.
You were led into a sitting room just off the entry—smaller, but no less grand. Ivory and pale green walls, antique gold filigree on the mirrors, a vase of white tulips in bloom. A woman sat beneath the window, her legs crossed, a small brown dog curled like a mink laid in her lap.
“Ah, thank you Edward, you may leave us,” she called.
The man who had led you in bowed his head and slipped from the room with the same noiseless grace he'd arrived with, the door sighing closed behind him.
She stood, lifting the dog with one arm, and extended the other toward you, palm down. You stepped forward, sliding your gloved hand into hers. Her grip was dry and faintly cool, like porcelain before the fire.
“Mrs. Castillo,” you said. “It’s lovely to meet you.”
“Evelyn, please,” she replied, smiling without warmth. “And likewise. You look older than your photos.”
Your stomach dropped slightly, but returned the smile anyway, polite and practiced.
“Must’ve been good lighting,” you said.
She blinked at that, the corner of her mouth twitching.
“Tea?” she asked, already drifting toward the lacquered table set with bone china and silver spoons.
“Yes,” you replied, smoothing your dress beneath you as you sat in the opposite armchair. “That sounds nice.”
She poured with a practiced hand, not bothering to ask how you took it. A twist of lemon slipped into your cup without fanfare.
“I wasn’t sure you’d come,” she said after a pause. “Most girls would’ve declined. Or sent a polite excuse through my son.”
“Why’s that?” you asked, reaching for your teacup without looking away from her.
She studied you back: your face, the line of your shoulders, the arch of your brow, the way your fingers didn’t tremble as they lifted the cup. She liked puzzles, you could tell. And you were one she was eager to crack.
“Oh, I suppose I can come off a bit… discerning,” she said, saccharine enough to sour the air as she sipped her tea.
You smiled again, sharper now. “All the times I’ve seen you at events, I wouldn’t say that’s such a bad thing.”
She chuckled a dry, elegant little laugh, like stones tapping against crystal, “You were the one in Givenchy at the Camford Gala last year. I seem to recall you correcting the ambassador’s French?”
Your fingers wrapped tighter around the delicate porcelain, though you kept your posture unchanged. “He misquoted Voltaire if I recall.”
“He did,” she agreed, her lips pursed. “Though most people wouldn’t have noticed. Or dared to mention it.”
You took a sip of your tea. “I suppose I’m not most people.”
Her smile lingered as she glanced out the tall window beside her, where afternoon light began to stretch across the floor in softened bands. The dog yawned in her lap.
“No, I don’t think so.” She set down her tea, her tongue licking the remnants before patting the side of her mouth with a linen napkin, “So tell me about this recent fiasco, this…late night debauchery.”
Your throat went dry, “I…I, well–”
There was a split-second moment where your heart started hammering against your ribs as you tried to remember what face you were wearing. You did not let your hands tremble, though the tea had suddenly lost its flavor.
You could feel her gaze bearing down on you, not aggressive, but pointed and deliberate, the kind of look that peeled back the silk of your dress and reached straight through to the scaffolding underneath.
And maybe that was what did it.
Your spine straightened, your gaze found hers. Because no, you wouldn’t fall apart like some silly, shaken thing in pearls and heels. You weren’t a girl anymore, and you weren’t stupid, and you sure as hell weren’t going to let this woman see you shrink.
“I hardly think a little partying ever did a girl wrong,” you said finally, the words smooth and evenly paced, your tone pleasant but not pliant, poised but entirely unmoved.
That earned a reaction. She tilted her head with the curiosity of a hound catching a scent. She studied you more closely now, her expression unreadable.
“I’m not sure I know what you mean,” she said, her voice light, but careful.
You looked her directly in the eye, the corners of your mouth lifting into a smile that wasn’t quite pretty and wasn’t quite friendly, but steady and sharp enough to hold its own.
“I mean,” you said slowly, “that I don’t believe I’m the first woman to drink too much champagne on her best friend’s birthday. I don’t think I’m the first person to stay out too late. And I certainly don’t think I’m the first woman to be photographed in an outfit like that, caught in a whirlwind of pervy paparazzi who will do quite literally anything for a high paying photo.”
Evelyn didn’t answer right away. She simply stared, her tea cup still raised, held just before her lips with both hands, her fingers contrasted against the fine porcelain. The dog in her lap shifted, sighing softly, but she did not move. Her eyes narrowed slightly with the quiet consideration of someone who had not expected to be challenged so directly, and perhaps, not so skillfully.
Something passed between you in the quiet that followed. You weren’t sure if it was understanding or maybe just recognition.
“Well,” she said, and though she tried to keep her voice measured, there was the faintest curl of amusement beneath it, like steam rising from the china she set down, “at least I can say you’re not boring like that last girl, the–oh, what was it? The matchmaker.”
“Being called boring might be even worse than being photographed topless on a night out.”
“I worried you might cry,” she said after a pause she poured another cup of tea for herself, her voice quiet, but not quite gentle. “Most girls do, when they are asked hard questions.”
“I’ve cried plenty,” you answered, lifting your tea for a sip, trying to sound casual now, “But not because someone is trying to make me. I cry on my own terms.”
“Good,” she murmured, mostly to herself. “Good.”
She glanced toward the window again, where the light was beginning to move toward the west skyline, casting the mid afternoon light across the trim of the furniture, gilding the edge of her profile. For a moment, she said nothing at all.
A long breath followed, so faint it hardly moved her chest, and then, to your quiet surprise, Evelyn Castillo let out a soft, unmistakable laugh. It was not cruel or theatrical, but something close to genuine. She looked at you again, and this time, the edge had dulled ever so slightly.
“My son told me not to ask about it,” she said, as if the thought had just drifted in on the breeze. “Which, of course, only made me want to.”
“Understandable.”
Her eyes met yours and held. The laughter faded from them as she took you in again, not just your face but the way you sat, the posture you kept, the stupid little outfit Margot put you in. Something unreadable passed through her gaze, something cooler than her smile, and you felt her studying you harder now, as if remembering herself.
“I want to know what you want from him.”
The words didn’t come out accusatory, but they held you like the edge of a knife to your throat.
“Excuse me?”
“Is it his money? His name?”
You straightened, your fingers tightening slightly on the edge of the teacup as you set it down.
“My family has more than enough of both. I’m not looking for any sort of—”
“Then what is it?” she asked, “Because forgive me, but I find it difficult to believe a woman your age is interested in my son for any reason other than what he can offer.”
“Harry is a good man, Evelyn. There’s more to him than—”
“Yes,” she interrupted, and for once, her voice softened. “I know.”
There was something brewing between the two of you as you stared at each other for a long, long moment. You could see it behind her eyes, something turning over in her thoughts, deciding whether or not to say whatever hovered at the tip of her tongue. Her gaze didn’t waver as she kept looking at you, still scrutinizing every inch of your face, every flicker of expression.
But eventually, her eyes dropped, breaking your stare. Her hands fell to the dog in her lap, manicured fingers grazing over its ears, absent and careful, like touching something familiar might help settle whatever had stirred in her chest.
“Forgive me,” she sighed, “my son is what we’d call a… a hopeless romantic. A mother can't help but want the best."
She returned to her tea, stirring it, and when she spoke, looking up at you again, the softness in her voice was so subtle it almost didn’t register.
“He’s always been, since he was a boy. The first time he ever had a crush, he was seven. He wrote the little girl poems, drew her pictures. She ignored him for days afterward, and he simply stopped eating. Wouldn’t come down for dinner, barely said a word, just sat in his room, thinking he'd done something wrong."
She glanced out the window, adjusting the sleeve of her blouse.
“He doesn’t know how to temper affection. When he falls for someone, it becomes his entire focus. And if it doesn’t work out, he assumes it’s a flaw in himself. That he miscalculated. That he failed.”
Your heart snagged on the image, held fast by it. Of Harry as a boy, tender and foolish and too full of hope.
Evelyn glanced up at you then, catching the way your expression had shifted, the way your fingers had stilled around the stem of your glass.
“You seem surprised.”
You opened your mouth, but no words came. You were, of course you were. You had seen Harry be his usual charming, distant, calculating, flirtatious self, but never…. Never vulnerable. Never wide-eyed and giving.
Well. Maybe just that one night. He’d given you a glimpse in as you shared cold Chinese food on his leather couch, when it was just the two of you. No gossip columns, no contract. Just the quiet warmth of his presence, the surprising softness in the curve of his smile. He had been real then. Earnest. Gentle in a way that had caught you off guard.
He’s always so quick to forgive. So endlessly patient, so disarmingly kind in ways you hadn’t expected from a man like him. And now…now this.
She gave a slow, careful nod as if watching your wheels turning in your head. “He’s never known how to do it halfway. That’s always been the problem. And when he gets hurt — which he always does — it ruins him.”
The silence that followed wasn’t heavy, but it settled over your shoulders just the same. You looked down at your tea, the pale swirl of lemon tracing lazy circles near the rim.
It felt like something like a little seed was placed in the soil of your brain, digging deep and rooting itself there.
Harry is a hopeless romantic.
And you weren’t sure if it was supposed to be a comfort or a warning.
Evelyn gathered herself and stood in a clear dismissal, her movements precise, her elegance untarnished, though her expression had shifted. There was steel beneath the silk now, cool and commanding.
“And that is why, Miss Montclair,” she said, offering her hand once more, her voice smooth as crystal, “I ask that you only carry this on with my son if you’re serious about him. About all of this.”
The heat rose behind your collar as you reached for her hand and stood. Her grip was light but final, a gesture that felt like it was sealing something invisible between the two of you.
“I understand, Mrs. Castillo.”
And when she dropped your hand, you turned on your heel, and you didn’t just walk — you escaped, your heels echoing against the marble as you pushed out the doors and into the foyer.
“Miss Montclair?”
You turned back, pulse kicking, throat tight. The sunlight slanted through the windows behind her, catching the edge of her cheekbone, the glint in her eye.
“Tell Harry to fire that stylist of his,” she said, already turning away. “She should know by now how much I detest celadon green.”
“Hey, you.”
“Hi,” you breathed, letting him lean in to kiss your cheek, the warmth of his lips brushing against your skin with simple familiarity.
The restaurant shimmered behind you like something out of a dream, all soft amber lighting and the low hum of conversation, the scent of fresh basil and salt and butter drifting in from an open kitchen where chefs moved like dancers behind frosted glass. There were candlelit tables tucked beneath pale archways, orchids floating in slender vases, and the faintest glint of silver catching candlelight like stars twinkling underwater. It was beautiful, inviting and luxurious in the simplicity of it all.
Harry guided you through the door with an easy hand at your back, following the hostess in a silk blouse, past the gold-leaf menus and velvet banquettes, until the two of you were seated in a quiet corner where the lights were low and the linen napkins had been folded into perfect thirds. Everything felt warm, and almost like it was waiting for something.
“So,” Harry said, unfolding the wine list with one hand and exhaling like he already knew the answer would amuse him, “how was tea with my mother yesterday?”
You stared at your menu, though the words blurred slightly.
You thought about how she watched you, how she poked and prodded, waiting for you to show your cracks. How she nearly saw the very edge of you — the place where your poise began to falter and your shame began to bloom, right before your spine built itself back up from the base, vertebrae by vertebrae, until you were sitting upright again with a smile on your face. You thought about the things she said about him. More than he let on, more than you were ready for. And how, by the end of it, you’d come to some sort of quiet truce.
“Fine,” you said, glancing downward as you turned a page in the menu.
Harry tilted his head slightly, peeking up at you from his reading, the corner of his mouth twitching with quiet delight. “Fine?”
You shrugged, still scanning entrées. “Fine.”
He chuckled under his breath and closed the wine list. “Well, she didn’t call to have me disowned, so I’ll take that as a promising sign. For her, I’d say that’s dangerously close to approval. How do you feel about Sauvignon Blanc?”
You lifted the menu to cover your smile. “How’s the lobster here?”
“Perfect,” he said easily, “And before you accuse me of ulterior motives, I do have something for you.”
“Buttering me up after sending me into the lion’s den?” you asked, finally peering over the top edge of the menu to look at him.
“Something like that.”
“No complaints from me,” you replied, setting the menu aside.
He reached into his coat and pulled out a small black box, the kind lined in velvet and weighted just enough to make your pulse flutter. Your eyes widened, and Harry laughed — a full, unguarded sound that lit up his whole face and made the candlelight flicker like it was in on the joke.
“Don’t make such a face,” he said, the grin still tugging at his mouth.
The waitress appeared, her voice soft and practiced. “Do we know what we’re having this evening?”
“Not yet,” he said, not taking his eyes off you, “but we’ll take the bottle of the 2017 Chateau, thank you.”
You reached for the box once she left with a nod, but hesitated.
“Harry Castillo, I swear, if Gossip Girl runs a headline about me being your child bride—”
“You’re in your twenties, Montclair.”
“Still.”
“Just open it.”
You took the box from him, your fingers brushing his for a second longer than necessary. When you opened it, the breath caught in your throat. Nestled inside was a gold Van Cleef bracelet, five delicate motifs gleaming beneath the soft restaurant light, inlaid with small diamonds that shimmered like snow under a winter sun.
“Oh,” you gasped.
“It’s just a thank you,” he told you, his voice softer now. “For not walking away, even though you were well within your rights to do so. For meeting with my mother and.... for still being part of this.”
You looked up at him, searching for something in his face that might explain why the gesture felt heavier than it should. “Put it on for me?”
He smiled at you—not the charming, rehearsed kind, but the one that lifted the corners of his mouth and made his eyes twinkle, the one that felt like it belonged only to these little moments — and reached across the table, carefully taking your wrist and fastening the clasp. His fingers brushed your skin, making your flesh pebble.
You reached for your bag when he let go. “I actually have something for you, too.”
You slid a matching black box across the white tablecloth. His expression flickered with curiosity, and then, as he opened it, shifted into something unreadable.
He frowned, just slightly.
Your stomach dropped. “Too much?”
“How did you—” he began, before shaking his head, pulling the Rolex out of its velvet keep. “How did you even pay for this?”
“I sell my underwear on the black market," you said, and his expression made you bark with laughter, "I'm kidding! My Instagram followers have kinda blown up since this began, thanks to you,” you said, your smile softening as you watched him take it out of its confines, “It’s just… a thank you. And maybe a small apology. Again.”
“You didn’t need to—”
“I wanted to,” you said quickly, your fingers brushing the base of the empty wine glass. “You’ve been… better than I’ve deserved. A great… business partner. In all of this. Even when I’ve made it difficult.”
Harry reached for your hand, releasing it from the wine glass and lifting it gently to his lips. The warmth of his mouth pressed against your knuckles, his breath soft against your skin, and for a moment the rest of the restaurant seemed to fall away.
“Not difficult,” he said quietly. “We all get our wires crossed sometimes.”
You flushed, not from embarrassment, but from the warmth he left behind when he pulled away. Just as he did, a camera flashed nearby, the sharp sting of light followed by a gasp, the stifling of voices like wind through leaves.
You turned your head instinctively, but Harry just smiled, letting his fingers trail over the back of your hand before releasing it, slow and unhurried.
In the dim light, the bracelet and watch on your wrists caught the glow like twin glimmers, mirror images of gratitude and something quieter, still unnamed.
“So,” he said, picking up the menu again like nothing had happened, “what looks good to you?”
Notes:
this has turned out to be such a slow burn and im sorry but I LOVE a slow burn heheheheheh it's started to get juuuuicyyyyyy
Chapter 8: What A Girl Wants
Summary:
Dinner was meant to be simple. Instead, it leaves you caught between who you were, who you’re expected to be, and who you can’t seem to stop thinking about. Hours later, you let it all bleed out where everyone can see.
Notes:
cw: vomiting
a/n: plz forgive me I realize some of this might be a wee bit corny but we all do it sometimes, no?
Chapter Text
Over the next few weeks, things begin to shift. Just in those quiet, sideways moments that make you pause without understanding why. There was a change, almost imperceptible, but you felt it all the same. Like a thread pulling ever tighter inside your chest or a single bead of water slipping endlessly down a windowpane. There was something crawling at the back of your mind — a little worm of thought, small and soft and persistent — and no matter how many times you brushed it away, it stayed, burrowing deeper, wriggling just beneath the surface. You felt it when you woke up, bleary-eyed and wrapped in silk sheets that still smell faintly of your Chanel perfume. You felt it when you would sip your morning coffee across from your mother, her eyes on her emails, steam curling between you like a wall. You could feel it when you were filling out applications for positions you don’t even want, still clinging stubbornly to the hope of employment that wouldn’t be handed to you by your father’s name. You felt it when you went to sleep, head pressing into the cool side of the pillow, thoughts trailing somewhere else entirely.
But most of all, you felt it when you were with Harry.
At your weekly meet-ups, whether it’s walking beneath the cherry blossoms in Central Park with lattes in hand, or lounging on a bench overlooking the water while the wind pulls at the hem of your Gucci dress, it’s always there. You could be leaning close across a marble bistro table sharing lunch, or sitting in a dark booth sipping martinis in a room humming with low jazz and the distinct smell of luxury — but that worm never leaves you.
Harry is a hopeless romantic.
Harry, who claimed love had always been difficult, and yet, had somehow made all of this feel… effortless.
Harry is a hopeless romantic.
And you don’t know why that sentence keeps repeating inside you like a prayer or a warning or something in between, only that it does. So yes, when he catches your eye over the rim of his glass of tequila and offers you that quiet, knowing smile, just as your own martini kisses your lips, you’re thinking about how the light from the sconces turns his eyes to honey. You’re thinking about how handsome he looks in that navy polo, how soft the line of his throat is beneath his open collar, how natural it feels to laugh at his jokes and plan your next appearance together and forget, for one stupid second, that it’s all pretend. That this man with his easy charm and his sharp mind and his too-generous smile is playing the same game you are, just from a different side of the board.
You’ve been ignoring the notifications on your phone more and more lately, letting texts and calls slip into silence while your mind is busy with planning the next photo op, the next restaurant, the next outfit that will look just right for the cameras. You’ve been shopping with Blair, slipping in and out of dressing rooms as she tosses silk and sequins over the top of the door, happy to assist so long as it’s not during her hours at Waldorf Designs or her increasingly erratic rendezvous with your brother.
“He’s been acting weird,” she said once, half-buried in a pile of chiffon and hangers.
You had shrugged, blaming it on Chuck’s usual springtime dramatics. He had a tendency to disappear during Gala season, to avoid the litany of questions from press and peers alike about his place in the family, about legacy, about marriage, about purpose. He always did this, you told her. It was routine. Nothing new. But Blair had only narrowed her eyes and pinched her lips, folding her arms like she knew something you didn’t.
“Something’s off this year,” she said. “It’s different. He’s different.”
You’d nodded, but your mind had already drifted, wondering whether the sapphire blue dress you were holding would match that steel-grey suit Harry planned to wear to the wedding for Dan and Serena. You’d turned toward the mirror, holding the fabric against your body, thinking about lighting, about shoes, about the angle when the flashbulbs went off.
You’d also been ignoring Nate’s calls. Not because he was being pushy or persistent in a way that bothered you — quite the opposite, really. He’d been kind, careful, patient in that quiet, golden-boy way he always was, leaving voicemails that were gentle, warm, never accusing. Just checking in. Just wondering how you were. Sometimes sending a photo of something you both used to laugh about, or a quiet little “thought of you” in the middle of the afternoon. He was trying, earnestly, sweetly, because the last time you’d spoken you had told him, maybe, one day, you’d go out with him again. And he believed you. He believed you because, at the time, you’d meant it.
But…what were you supposed to say?
Sorry, Nate, I’m in a fake relationship with a man who barely knew me a month ago and now takes me to tea at the Carlyle to distract the press from his niece’s rehab.
Sorry, Nate, the last time I saw you, Harry responded by drafting a binding legal document.
Sorry, Nate, it’s not that I don’t miss you. It’s just that my pretend, very not real boyfriend is planning to take me to the Ritz Carlton for drinks tonight so we can be photographed by Gossip Girl and end up on the front page of the tabloids instead of said niece.
Yeah, that’d go over well.
And maybe that’s why, when your parents told you they’d made reservations at Nobu on a friday night and asked you to join, you said yes without thinking. You didn’t think to ask who’d be joining. You’d expected a regular night out with your parents, a cup of warm sake and sashimi salads with your mom, Chuck absent as always, and your father talking to the owner and asking how business was while you avoided any talks about job interviews or apartment searching.
You surely, most definitely, were not expecting to see Nate there.
Those blue eyes and that messy, perfect hair, the way his entire face lit up when he saw you, like you hadn’t been dodging his calls for weeks. No, no, you hadn’t expected any of that.
“I—” you stammered, turning toward your parents, “Mom, what—?”
Your words tangled as you froze, standing over the table, hand still clutched around the strap of your purse, heels sinking slightly into the plush carpet.
“Nate here was just telling us about his recent meeting with the mayor,” your father said, all good cheer and no awareness, tapping the cushion of the empty chair beside him, and you knew it was his gentle way of telling you: sit down and behave.
“He also mentioned,” your mother added with a smile that didn’t quite reach her eyes, “that you’ve been ignoring his calls.”
You stayed there, standing beside the empty chair, feeling the heat creep up your neck as Nate looked at you with something between hurt and bashfulness in his gaze like he didn’t realize they’d start interrogating you this soon.
Eventually, catching your breath, you sat down across from him. Your eyes danced across the room around you, grateful you didn’t see any cameras or people watching.
“Care to explain yourself?” your mother asked, her voice light, curious, but dipped in expectation. It was the same voice she’d used when you were seventeen and late coming home, the same one that had always made your jaw clench and your shoulders coil. Making you feel so small.
You kept your expression smooth and unbothered.
“Hi, Nate,” you said, ignoring her question, turning toward him with a soft smile that was real enough to make the moment pass. He smiled back with a quiet hello, all bashful sweetness, and there was that familiar pull in your chest, warm and stupid and nostalgic. You didn’t want to make him feel bad. He didn’t know what he was walking into. You did.
“Warm sake for the table, please,” you said quickly to the waiter as they appeared, cutting off whatever comment your mother had lined up next, “and maybe a Sapporo too.”
“Beer? Really?” your mother asked.
Your father raised a brow but turned to the waiter all the same. “Make that two, please.”
“Three,” Nate added, smiling as he folded his hands on the table.
Your mother exhaled through her nose, setting her menu aside. “Green tea for me, thank you.”
The waiter nodded and disappeared, leaving behind a silence that pulsed like a nerve just beneath the skin.
Her eyes found you again.
“Don’t you think you ought to take it easy on the alcohol, dear?” she asked, in that way she always did — not judging, of course not, just concerned, just gently implying, just twisting the knife with the faintest flick of her wrist.
You didn’t bother looking up from the menu. You’d memorized it years ago, could order in your sleep, but you turned the pages anyway, letting the glossy paper shield your expression as your mouth curved into something sweet.
“Oh, have some fun, Mom. We’re out for a nice dinner, with nice company,” you said, the words syrupy and smooth as you lowered the menu just enough to wink at Nate.
He chuckled softly, eyes meeting yours, and it soothed something inside of you, remembering nights out and days spent with him so many years ago.
Your mother said nothing, just pursed her lips and reached for her napkin, smoothing it over her lap.
And then, just as the conversation threatened to teeter again, your father cleared his throat and leaned forward, pulling the attention back into his orbit with practiced ease.
“So, Nate,” he said, clasping his hands together with a kind of ceremonial delight, “tell us more about this electoral run of yours. I hear the numbers are looking promising.”
You barely registered Nate’s polite response, the way he straightened slightly in his seat, voice low and measured and every bit the picture of a man becoming exactly who he’s meant to be. Because suddenly, your stomach dropped, hollow and fast, like an elevator falling through the floors. Your lungs couldn’t fill properly. There was a flood in your ears with a hot, rushing sound like blood and waves and too many thoughts crashing into each other.
Across the room, near the bar, half-shadowed by a carved pillar and a bloom of white orchids arranged in a glass vase that caught the light, sat Harry.
He wasn’t alone, but seated beside him was someone who looked like a colleague, an older man in a dark gray suit gesturing as he spoke, his voice animated, his expression lively, but Harry’s posture made it clear he hadn’t heard a word. His elbow was braced casually on the edge of the marble bar, the line of his jaw sharp in the warm, amber light, his mouth unreadable, his eyes nowhere near the man beside him.
No, his eyes were on you.
Black and bottomless from across the room, they locked onto you like a vise, unflinching and full of something that made your skin heat beneath your collar, something that sent a flicker of panic across the inside of your ribs. You didn’t move. Not until the waiter reappeared beside the table with a tray of drinks and poured the first round of warm sake into the ceramic cup in front of you. Only then did you blink, reaching for the cup, and you shot it back in one motion like it was tequila on a rooftop with Blair and not dinner with your parents and an ex boyfriend from three lifetimes ago.
“Jesus—” your father cursed, whispering your name in vehemence.
“I need to pee,” you said, not waiting for permission, already pushing back from the table with a clatter that turned one or two heads, already moving, already walking away.
You moved fast through the dining room, past the curve of the hostess stand, down the dim hallway lined with flickering sconces and framed black-and-white photographs of celebrities who had long since died of overdoses and a life of fame. You didn’t make it far.
A hand caught your arm just before the corner and in the next second, you were pulled, spun, pushed against the wall with your back pressed flush to the cool plaster. Your breath knocked from your chest by the sheer presence of him. It was vertigo inducing and fast, but not rough or cruel.
“Tell me I’m seeing things,” Harry said, his voice low and sharp and slicing through, like needle across skin. You didn’t open your eyes. You couldn’t. You didn’t want to see what lived in his expression right now. The anger or the heat or the betrayal he hadn’t earned the right to wear. Or had he? It was all so confusing. You breathed through your nose, long and shallow, your eyelids locked down so tightly it almost hurt as you shook your head.
“I didn’t—”
“I’m fairly certain this falls under the category of things very clearly stated in the contract,” he interrupted, his voice tightening, “things I was very specific about not being okay with.”
“My parents told me to come to dinner,” you said quickly, every word crisp and short and cracking. “I didn’t know—”
“To think everything had been going so well,” he said bitterly, “and all this time you’ve been seeing him, what, behind my back?”
“No!” you said, louder now, trying to cut through the sting of his tone. “Harry, Jesus, listen—”
“What part of ‘appearance of exclusivity’ and ‘abstaining from romantic relationships’ was unclear to you?” he snapped, the words falling cold and polished from his mouth like glass off a table.
“Would you just listen to me for one second!?” you hissed, your eyes flying open, fury meeting fury in the narrow dark of the hallway. Your chest rose with each breath. Your vision blurred for a moment, not with tears, but with rage and sheer indignity of being accused when you hadn’t even known you were playing the game wrong.
He looked like he was about to say something else, but you got there first.
“I didn’t do this,” you snapped.
Your voice wasn’t gentle or soft or designed to win him over. It was sharp and fast and fraying at the edges, because you were so tired. Tired of being questioned, managed, and trapped inside someone else’s idea of what your life should look like all the god damn time.
“I didn’t know he’d be there,” you bit out. “My parents set me up. They didn’t tell me.”
Harry stared at you, breathing hard, jaw clenched, but you pushed forward.
“I came here thinking it was just dinner with my parents, Harry. I didn’t plan for him to be here. And I sure as hell didn’t do it to hurt you.”
The silence snapped closed around the two of you. Your back was still pressed to the wall, and hands that were still on your arms pinned you in place.
You couldn’t breathe right. You couldn’t think right. Because somewhere behind your anger, behind your embarrassment and exhaustion, that same stupid worm kept wriggling its way through your skull, digging in deeper now. Because the way Harry was staring down at you, the way his hands tightened on your arms, it didn’t feel contractual. And as much as his eyes were a deep, dark, molasses brown, the green in his shirt had started to reflect in them, catching along the edge of his stare like a shadow.
You let out a breath through your nose when he didn’t say anything. “God,” you muttered. “You don’t even trust me enough to ask first.”
Looking back, you could’ve named the look in his eyes now, as he moved forward. And maybe, because of that, you should’ve told him that no one was watching, that there were no cameras hiding in the hallway, no eager eyes ready to feed this to the tabloids, that this wasn’t a scene and you weren’t playing a part. But in that moment, you didn’t want to stop him. You let him come closer. You let him reach.
His hands released from you finger by finger, but not entirely falling away. His touch trailed up your skin, brushing up your arms, over the slope of your shoulders, along your throat, and finally around your face, his palms cradling your skull. His nose nearly touched yours as he leaned in, and your chest barely moved as you inhaled. You weren’t thinking clearly. You didn’t think you were thinking at all.
Harry is a hopeless romantic.
Harry is a hopeless romantic.
Harry is a hopeless romantic.
And he kissed like one too.
His lips, soft and full, met yours with the kind of careful grace that made your stomach flutter. It was tentative at first, like he wasn’t sure he had permission, like he was waiting to be told no. And then something shifted. And maybe it was the way your breath caught or just the dam breaking after too long of pretending. Because suddenly, he was on you in a frenzy, tongue pushing past the slant of your mouth before you could even think to stop him, and you didn’t want to. You opened for him without fuss or fight, your hands flying up, suddenly desperate, clawing, gripping fistfuls of him just to feel him, to anchor yourself. His mouth devoured you, wet and hot and demanding, claiming you, biting at your bottom lip like he was angry with it, like he’d been starving for the taste of you and couldn’t believe he’d waited this long. He drove you backward with each press, pinning you harder to the wall, pressing his entire body to yours until there wasn’t a breath of space left, until you could feel every solid inch of him through his suit, burning and alive and impossible to ignore.
It wasn’t polished or poised or camera ready. Nothing like the sweet goodbye kisses or pecks in the park you’d shown Gossip Girl to prove anything. This was needy and feral and starved. It was like something had clawed its way out of both of you in gasps and heat and the nauseating ache of having wanted something for too long.
When he pulled back, it was as if everything he’d done came crashing down all at once. He stumbled a step away from you, breath shallow, shoulders tense. He moved fast, retreating until his spine hit the wall opposite and he stayed there, eyes wild and unreadable, the silence swelling between you like a tide.
It was only a few feet, but it might as well have been miles.
He brought the back of his hand to his mouth and wiped it slowly as his head tipped back, gulping in fitfuls of air into his lungs. His eyes shifted, never towards you, but towards the dining room with a distant sort of look in them.
“Harry—” you started.
“Enjoy your dinner,” he cut in, his voice low and rough and nothing like the sharp, hissing from only moments before.
You blinked at him, still breathless, your fists curling tight at your sides, nails biting into your palms, your fingers still tingling where they’d twisted into his jacket. Your whole body still ached with the heat of him.
“Wait—” you started, but he was already walking away, shoulders squared, footsteps sharp, the dining room swallowing him whole before you could say anything else.
You’d pulled apart your entire wardrobe, ransacked every shelf and drawer, leaving silk and sequins and scraps of chiffon draped over every surface like the aftermath of a fashion hurricane. Shoes littered the rug in mismatched pairs, hangers dangled from lampshades and drawer knobs, and your closet doors hung open like wounded things, emptied and gutted. It was forty-five minutes past ten and you hadn’t even pretended to try and sleep.
Blair’s face flickered on your phone, propped against the glowing bulbs of your lacquered vanity. Her face was glossy and glared from the lights against your screen, eyes half-lidded and amused where she sat in some dark lit space as you held another rejected top at arm’s length like it had personally offended you.
“I just need a night out, B!” you said, breathless with rage, flinging a lacy black blouse over your shoulder where it landed in a pile near the bookcase and unopened Dior bags. “I’m so—”
You reached for the next hanger. “—sick—” a sheer barely-there cream camisole that shimmered like spilled milk, “—and tired—” a velvet, sleeveless turtleneck you’d convinced yourself was sophisticated once, now crumpled onto the floor. “—of being this perfect, prim little wind-up doll for these people!”
Blair raised a brow. “Which people, babe?”
“My parents,” you snapped, throwing your arms out dramatically, a denim mini skirt flying into the other room, “And Gossip Girl and the entire damn city, honestly!”
You paused mid-rant as your hand brushed across something glinting. Soft gold sequins stitched into a backless, cowl-necked slip. You held it up to the light. It was a little scandalous, a little dangerous and scantily tied with a strap tied at the neck.
Blair squinted through the screen. “I was gonna stay in and force Chuck to finally watch Breakfast at Tiffany’s, before the wedding tomorrow but…I could be talked into a bottle of champagne at The Box.”
You didn’t hesitate. “Perfect. Want to come over and get ready, or just meet me there?”
“I’ll meet you,” she said, adjusting her camera angle, showing the dark blur of the town car interior behind her. “I’m already out—Chuck had some meeting and I’m waiting in the car.”
“Where are you, anyway?” you asked, still staring at the dress like it had the power to change your night around.
“Uh—oh, he’s here. Gotta go, see you in a bit!” she said quickly, hanging up before you could ask another question.
You blinked at the screen as the call ended, then huffed, tossing your phone through the double doors of your closet and onto the bed. “Weirdo,” you muttered, grabbing the gold slip off the hanger.
By midnight, the table in the corner was barely recognizable. Half-empty champagne flutes glittered in the purple lights, cocktail glasses sweat against mirrored trays with their garnishes limp and melting. The air was syrup-thick with perfume, liquor, and the low throb of bass that seemed to pulse beneath your skin.
You were standing on the velvet banquette in your strappy stilettos, that little gold slip clinging to your body like it had been sewn on wet. Your hair was wild from dancing, cheeks warm from champagne, and laughter bubbled in your throat.
Chuck was stretched across the booth, one arm tossed around the back of the seat where Blair sat beside him, the other wrapped around a bottle of Dom. His shirt was mostly unbuttoned, his tie hung around his neck like a loose noose, and he looked entirely too pleased with himself as he stared at Blair like she’d hung the damn moon.
“They’re gonna have to bleach this couch tomorrow,” you shouted over the music, pointing at the two of them as they kissed as if they hadn’t been doing it for nearly a decade.
Blair pulled back, scrunching her nose in that Waldorf way, “You’re just mad we’re in love!”
“And I’m mad that I didn’t bring a second bottle,” Chuck said lazily, raising the one he had and toasting you with it before taking a long swig straight from the mouth. “God bless the American dollar.”
The club had filled with bodies by then, the room a tangle of limbs and heat and synthetic beats, some pop remix rattling the walls. You danced with your arms overhead, hips rolling lazily to the rhythm, the hem of your dress flirting with indecency. The music was stupid and loud and so infectious, but you couldn’t bring yourself to care.
You’d spotted Jack Antonoff on the dance floor sipping his beer, arm slung around some new singer who was dancing in a leather dress with safety pins down the side. At some point, you remember Troye Sivan floating by, shirt sheer and smile blinding, mouthing You look amazing before disappearing into the crowd again.
Another bottle appeared like magic, escorted by a girl in a black bustier and heels too high for the tray she carried. Glass clattered against glass as she set down a round of shots, lime wedges slick with condensation.
“These are from the booth across the room!” she called, voice barely cutting through the sound.
You blinked past the lights, shielding your eyes, and there was Zayn, all teeth and trouble, holding up a shot glass like a peace offering while his friends laughed behind him.
You let out an excited squeal, grabbing two shots, handing them to Chuck and Blair, who were still tangled up with their tongues down each other’s throats in the booths corner. The others around you, a few randoms that people Blair knew from the last fashion show or the fit models for her company, grabbed theirs too. You cheers’d mid-air in Zayn’s direction, tossed yours back in one go, the liquor warming a path down your throat before biting into the lime wedge. You were tipsy, warm and glowing, the buzz of it all making everything soft at the edges.
“Hey!” Blair shouted, tapping your thigh with something glowing in her hand.
You looked down and saw her holding out your phone, screen illuminated in the dark red and purple lights. You crouched, reaching down, nearly tipping over into the table like a baby deer.
“Get down before the night ends up with you in the ER, would you?” Chuck slurred, his shirt completely open now, hair a mess.
“Party pooper,” you grinned, flipping him off and staying right where you were.
But your smile faltered as your eyes focused on the screen.
Harry Castillo was calling.
The music didn’t change. Blair was still letting Chuck mouth something filthy along her collarbone. Zayn and his friends were still laughing across the room. The DJ was still yelling into the mic. But something inside you shifted hollow and cold and furious.
You hit answer.
“Hellloooooo?” you sing-songed into the phone.
“Where are you?”
“Wouldn’t you like to know.” You giggled, letting your hips sway again as a club version of a Doja Cat song rolled over the crowd.
“No need. I see you.”
Your heart gave a sudden, traitorous thud, but your body kept moving, almost defiantly. Another buzz hit your palm, and when you looked down, a Gossip Girl update flashing on the screen with a blurry shot of you mid-dance.
“Don’t tell me you actually signed up for Gossip Girl alerts?”
“It’s the only way to keep tabs on you,” he said, and you hated that you could hear the strain behind it, like he was gritting his teeth through every word.
“Cute,” you said, your voice honey-slick with mockery. “You miss me.”
There was a pause, but it didn’t last long. “Go home, Montclair.”
You laughed once, sharp and humorless. “You know,” you said, letting the words tumble out while you had the false, liquor-induced confidence, “you wouldn’t need to keep tabs if you hadn’t stormed off earlier. Maybe try staying long enough to talk about it next time.”
He veered the conversation left faster than you could catch up to, “You do realize it’s Serena’s wedding tomorrow? You’re going to be hungover. Go. Home.”
You rolled your eyes so hard it made your vision tilt.
“Awwww, sorry, Daddy, but I’m a big girl now. You can't tell me what to do.”
“And whose money are you spending tonight, big girl?”
You didn’t even hesitate. “Article five,” you said, stumbling over your own laughter, “section C—you remember that part, don’t you? About ‘appearance upkeep’?” You dropped your voice into a sing-song again, saccharine and smug. “I’m keeping up appearances, Harry. I’m out here being your stupid, ditzy party dream girl. You should be thanking me. In fact, Rubert fucking Murdauch should be writing me a check for how many magazines he sells with my god damn name as the headline!”
“Watch your mouth,” he snarled, “Stay there, I’m coming to get you.” You didn’t give him the satisfaction of hearing your breath hitch. “Don’t bother,” you snapped, and before the burn of his silence could spread, you hung up and threw your phone into your bag, the music swallowing the moment whole.
You’d drifted over to Zayn’s table not long after, weaving through the crush of bodies and flashing lights, a glass still clutched in your hand. The club had filled to the brim by now, thick with perfume and sweat and flashing strobes that turned everything colorful and electric. You tossed your hair, smiling as you reached their booth, leaning in to thank them for the shots.
Zayn pulled you in for a friendly kiss on the cheek, flashing that sleepy grin of his, and you laughed, your fingers clutching the velvet cushion as you took a seat. You recognized a few of the others lounging in the corner—one had been a few years ahead of you in school, another you’d matched with on Raya weeks ago and never messaged back.
And sitting closest, tall and impossibly pretty in a sleeveless black tee and Cartier around his wrist, was Alton Mason. You’d seen him on the cover of Vogue just last month, styled in leather and lace with a cigarette barely hanging from his lips. He looked just as expensive now, a double shot of Hennessy in his glass in hand, watching you with a smile like he already knew what you were about to ask.
You ended up on the dancefloor with him before you could think hard enough to stop yourself. The music was filthy, the bass rattling your ribs, and the air so heavy with heat and perfume it was practically dripping. Alton’s hands found your waist with an amused little laugh, steadying you as you moved against him, loose and carefree and just drunk enough not to care who saw.
You grinded against him lazily, knowing full well it meant nothing — not with Alton, who’d already told you you were his “favorite girl to party with” ten minutes ago. He was your safety net, cheering you on and letting you have your moment while the crowd pulsed around you and the lights danced across your thighs.
You tossed your head back, caught in the thrum of it, letting the world blur. Let Gossip Girl get their pictures. Let Harry see them.
And maybe he already had—because just then, you felt something. It was an innate human sense, one that prickles the edge of your neck, a tether hooked through your chest, one that knows where to look almost instinctively in the direction of danger.
The sting of a stare.
You held your breath as you met his eyes.
Leaning against the upper railing, he looked like he’d been carved out of stone. Out of place in the crowd, too still, too sharp. Standing as if the night hadn’t touched him at all, was Harry.
His hands rested on the rail, his jaw tight and gaze unblinking. As though the room swelled and pulsed around him, he only saw one thing.
You looked around instinctively, finding that Blair was still in the booth, half-draped in Chuck’s lap again, but she clocked Harry the second you did. She caught your eye: you good? and when you nodded back, she relaxed into your brother.
But Harry was already moving.
He shouldered his way through the crowd like a storm, black coat flaring behind him, the club’s heat parting around him. You didn’t even have time to plant your feet before his hand found your wrist.
“Hey—” you started, but he was already tugging.
He didn’t say a word as he pulled you from the floor. You didn’t resist, exactly, not when the music was deafening and everyone was watching. You only turned to try to give Blair a silent goodbye, but she was already lip locked with Chuck again.
Outside, the night air hit you like a slap. The spring chill was still biting, hanging onto the remnants of winter as it sliced through the heat that clung to your skin. You yanked your arm free and staggered back a step, swaying when he tried to walk you to his black Mercedes.
“Jesus Christ, Harry,” you hissed, hugging your arms around yourself. “You think you can just manhandle me like that?”
He looked down at you, eyes fuming with red, “What the hell was that?”
“Partying. Like I’m allowed to.”
“You were grinding on some kid.”
“Oh, calm down. I’m almost certain he’s not even into girls—”
“I don’t give a damn what he— and you were practically—” he snapped, faltering, but stopped and collected himself with a big breath in through his nose. “You can’t act like that when people are watching your every move right now.”
You opened your mouth, some snarl already half formed on your tongue—but it didn’t come out. Instead, your stomach turned with too many shots and too much sugar. You hadn’t eaten a bite of dinner earlier with your parents, it had all tasted like ash after you'd left the bathroom.
Without warning, you doubled over and threw up onto the curb.
Harry was there in an instant, one hand on your back, the other gently gathering your hair out of your face.
“Hey, hey. Come on, sweetheart. I’ve got you.”
You gagged, wiped your mouth with the back of your hand, blinking tears out of your eyes. “Don’t—don’t call me that.”
He didn’t answer, just waited as you straightened, breathing through your nose. His hand was still light on your back, steady and warm.
“I’m fine,” you muttered.
He sighed, soft, almost tender. “Let me get you out of here.”
You hesitated.
“Please,” he added, and this time, his voice cracked just slightly around the edges. “Let’s just go.”
You acquiesced, the street feeling too loud, the club too far, and your skin too cold to argue anymore.
He opened the car door for you and you slid in, head swimming, chest still burning. He didn’t say another word as he joined you, and neither did you.
Chapter 9: Champagne Problems
Summary:
You wake up somewhere unfamiliar, the night before a blur. There’s a dress waiting, a face to put on, and a wedding to get to. The day unfolds like a minefield with emotions running high, joy and tension tangling together. And when the night ends, it’s not quite what the way you expected.
Notes:
nice loooonggggg chapter for you today. thank you for all your patience and love! I hope you like it!
Chapter Text
You knew immediately something was off.
The sheets weren’t yours, for one. Easily a thousand threadcount, soft and cool to the touch. The scent in the room didn’t belong to you either, a clean, muted blend of detergent and cologne threading the air as you blinked your way awake. A dull ache pulsed behind your eyes, the throb of a hangover pounding like a pendulum through your skull. Somewhere nearby, a clock ticked faintly beneath the hiss of a white noise machine you’d never use.
You opened your eyes to a cream-colored wall, the softness of the light gently wrapping around the edges of the room. Beside you, a dark-stained oak nightstand sat spare and clean: a glistening glass of water and a bottle of over-the-counter painkillers sitting atop it with nothing else. No phone, no chocolate wrappers, no haphazardly thrown bra over the side of it.
Definitely not your room.
You sat up slowly, the movement making your brain slosh in your head. You brought up one hand to rub a fist to your eye, rubbing the sleep away, while the other reached for the water, nearly draining it in one go. But your eyes landed on the pain meds, pausing, realizing that you definitely needed them too, swallowing a couple before downing the rest of the glass.
The gold slip dress still clung to your skin like static, twisted from sleep and sharp against your ribs. You winced, tugging at the fabric, desperate to peel it off. The room, though simple, was elegant in its restraint—clean lines, warm light bleeding through layers of gauzy curtains, the skyline casting golden streaks across the floor. But it was too tidy, so impersonal. The bed was large, too large for only one person, and the lack of…anything else in the room made it clear this was no master bedroom. It bore no character or charm or personality the rest of the home had adorned the last time you’d been here.
You got up when you saw draped over a leather chair in the corner: a crisp, pinstriped shirt, joggers and Comme Si socks, folded neatly. You reached for the note atop the pile, a thick notecard, expensive stock, inked with a sharp scrawl.
In case you wake before I pick up your dress. — H
The worm that had been burrowing into your brain for weeks twitched with something like delight. But you buried it fast, replaced it with a simmering irritation. Who was he to lay out clothes like you were his to dress? To collect your things like you’d already handed them over? Had you? When?
You scowled at the note, but the discomfort of the sequins eventually overruled your pride. With a huff, you stripped out of the dress, letting it fall to the floor in a glittering heap. The shirt was enormous on you, the socks even more absurd, but warm and soft. You left the joggers, hardly needing them with the way his shirt swallowed you.
And when you’d marched to the bathroom, you weren’t even surprised to find an unopened toothbrush and toothpaste waiting for you. Asshole.
Eventually, you emerged into the golden quiet of his apartment, everything still and glowing with that early morning hush. The city beyond the windows glittered behind the curtain’s soft veil, and you wandered past the familiar leather couch, the shallow bowl of change and keys by the door, past the row of records and the open book facedown on the side table. The space didn’t scream bachelor pad, it hadn’t when you’d been here weeks ago. No, it simply whispered its wealth and lived in comfort. Everything felt so thoughtful, masculine, and steady, even in the morning light.
You found yourself scanning the bookshelf before you even realized you'd crossed to it. His collection was less curated than you expected—not just finance and politics, but a handful of weathered novels tucked between hardbacks on famous writers and architects. A copy of Just Kids with the spine broken and dogeared. You brushed your fingers across it, wanting to see what he’d left in the margins.
The elevator chimed.
You turned as Harry stepped through, sharp and starched in a dark suit that looked like it had been tailored around the angles of his body. His hair was neat with a single curl breaking free down his forehead, his hand casually draped over a hanger and a gray garment bag slung behind his back. He paused when he saw you, and for a second, the air between you went very still. You watched as his eyes trailed down over the bareness of your legs, back to the hem of the shirt, up to your face.
Then he blinked and said, “Good afternoon.”
You blinked back. Shit. How long had you slept?
He crossed the room without further comment and laid the bag carefully across the couch, the faint edge of pale yellow satin slipping into view from beneath the plastic.
“You need to be ready in an hour,” he said as he straightened. “Do you need anything?”
You shifted, bare feet curling into the rug, suddenly too aware of the shirt hanging loose around your thighs. “No…well—” You hesitated, hating how small you sounded.
His gaze held yours, patient but expectant.
You hesitated. “Did we… last night, when we got back…?”
The question felt ugly on your tongue, thick and sour. You hardly wanted the answer, but it pushed out anyway.
“You don’t remember getting back?” he asked, concern threading his brows together.
You shook your head slowly, ashamed.
He sighed, “Nothing happened, I wouldn’t do that.”
“I know.” you said softly, and you did. But still, waking in someone else’s place, foggy brained in one of the skimpiest dresses you owned with your heels kicked somewhere you didn’t recall kicking them…it made the back of your throat hollow until he said it plainly. And hearing it from him settled something in your chest. You let your shoulders drop.
“My makeup,” you started, circling back to his question, “my hair…I didn’t—I don’t have—”
“No matter,” he said, glancing back over his shoulder just as the elevator dinged again.
Margot swept in like a gust of spring wind, all smiles and perfume and polished heels. “No green today, I promise!” she sang, racketing your brain around your skull as she pulled you into a quick hug and steered you toward the second sitting room.
You looked back once, just before the door closed behind you. Harry stood at the window, hands at his hips, staring out at the skyline.
“George, I am quite literally begging you,” you said, voice still thick with irritation as you leaned your head back against the buttery leather, “please tell me we can stop for a latte. And a sandwich. A real one—with egg and cheese.”
In the rearview mirror of the town car, George caught your eyes with a conspiratorial grin, his tone teasing and mild as always. “Did Mr. Castillo not see to your breakfast this morning, Miss Montclair?”
“As a matter of fact, he did not,” you deadpanned, though the smile was already tugging at your lips.
“She woke up at one o’clock,” Harry muttered beside you, his voice clipped and even, eyes still fixed on the screen of his phone as his thumb moved methodically, scrolling through something you couldn’t quite see. “We were on a tight schedule.”
George wisely said nothing, though the corners of his mouth twitched, and you watched Harry’s jaw tighten just slightly in response.
“We’ll stop at La Colombe,” Harry added after a beat, not bothering to look up. “It’s on the way. Will that suffice, Miss Montclair?”
You turned toward him slowly, letting your expression fall somewhere between mock gratitude and mild contempt. “Yes. I think it will. Thank you.”
He hardly flinched, just a tick of a mirrored grin as he glanced at you before returning to his phone. The glow of the screen illuminated his jaw, reflecting blue in his otherwise dark eyes. You leaned in just slightly.
“Checking for overdraft fees?” you asked, voice sweet as syrup.
His brow twitched. “With the way you were spending?” he murmured, “Who knows what I’ll find.”
You huffed through your nose and leaned back in your seat, folding your arms across your chest. The dress he’d left for you: pale yellow, silk, delicate as breath draped across you in simple elegance. The thin straps rested gently over your shoulders, the skirt whispering over your thighs as you crossed one leg over the other impatiently.
He tilted the screen closer, sliding on the reading glasses he kept tucked away in the back pocket of the driver’s side, still in their Prada case, awaiting use. “Let’s see…three bottles of Dom Pérignon, each at seven hundred. A round of shots I can only assume must have been laced with gold: three hundred. And what in the hell is this—” he paused, squinting, “two hundred dollars on Venmo to someone named... @/FairyGodFucker27?”
You shrugged exaggeratedly, “She was doing palm readings!” your voice was high, potentially too high, defensive as you added: “She told me she was saving up for a car. I liked her! So what if I gave her a little extra?”
“Did she at least say anything useful?”
You looked out the window, shaking your head in exasperation before pausing, and putting on your more saccharine smile to look at him. “Actually, yes. She told me I’d die at thirty-four, be married three times before then, and that my fake boyfriend is a very jealous, emotionally repressed, big fat meanie.”
Harry was quiet for a moment. Then, looking over at you, he said: “She specifically said ‘fat’?”
You shot him a sharp look, grin dropping, but he smiled—slow and unrepentant.
“Shut up,” you muttered, but your lips curled against your will, and the air between you lightened for just a moment.
By the time George had pulled into the coffee shop and handed you your goods, the caffeine withdrawal headache had begun to fade. The hot sandwich wrapped in parchment was perfectly toasted, and by the second bite, you felt something like human again. The salt and fat and sugar soothed whatever ache still clung to the edges of your hangover, and the silence between you and Harry settled into something gentler.
You glanced at your reflection in the car window, then at Harry’s side profile—the angle of his jaw and the neatly trimmed scruff there, the tension that seemed to live permanently between his brows. You pulled out your phone and shifted slightly closer to him on the bench seat.
“Come here.”
He looked at you, eyes narrowing.
“For Instagram,” you said flatly.
He obliged with no further commentary, adjusting himself beside you, that green ring flashing on his finger as he rested his hand on your thigh. You raised your phone, snapped a few photos with your coffee nestled in your lap, your camera angled just right to catch the morning light across your lap. His thumb moved absently, slowly brushing back and forth across your leg. You reasoned it must’ve been subconscious, he didn’t even realize he was doing it.
Still, it made your stomach flutter in a way that annoyed you.
You scrolled through the photos, settled on one, and began editing. Harry’s hand didn’t move away as he watched you.
“Didn’t Serena say this would be a phone-free wedding?” you murmured without looking up, something tugging at your memory from the invitation.
“Her mother told me they’d be collecting them at the door.” Harry said.
“Geez,” you breathed, adjusting the brightness on the photo.
You tapped ‘Post’ and watched the image go live.
“Well,” you added with mock formality, slipping the phone back into your bag, “I suppose that counts as our weekly appearance.”
Harry gave a small shrug, withdrawing his hand from your leg. “If you wish.”
You turned to say something, but his phone was ringing, and he was answering it—his voice lowered and posture shifting slightly, his attention gone. You looked out the window, coffee cool between your palms, the last traces of your smile fading as the city passed in blurs of steel and stone.
The wedding was beautiful in the way Serena always was — radiant, thoughtful, effortlessly golden. The rooftop was dressed in soft light and champagne florals, the skyline behind the altar glowing as the sun eased across the city sky. Gold chairs, delicate glassware, velvet programs with thick ribbon spines. The ceremony was small, just a few rows of friends and family, quiet and intimate beneath the chandeliers suspended from the tented canopy. You sat beside Harry with Blair and Chuck on one side, both of them a little cold while your parents were on the other, and somewhere nearby, Nate with his mother. Chuck whispered something in Blair’s ear that she didn’t respond to, her look of controlled neutrality pinched with irritation. Your mother, meanwhile, kept making little noises of disapproval under her breath, just audible enough to register. Her eyes flicked toward you anytime Harry leaned close, her discontent barely disguised while your father remained in cool neutrality. Harry held your hand in your lap, fingers laced with yours, the perfect image of a couple unfazed by the tension pressing in around them.
By the time cocktail hour began, the guest list had more than doubled. Familiar faces began to appear as the party opened up to more guests—editors, designers, Serena’s well-groomed Rolodex of socialites and legacy friends. Dan’s people too: old Brooklyn friends, including Vanessa, who gave you a warm but cautious hug and asked about your life with a note of concern in her voice you tried not to internalize. So many people you hadn’t seen in years. Ghosts of that old New York—of highschool parties and drunken brunches that gave the illusion that life would always be gifted and unfolding in front of you.
Harry excused himself to grab you a drink, and you found yourself wandering to the edge of the crowd when Serena materialized beside you in her gown, radiant and breathless.
“I have someone I’d like you to meet,” she said, glowing.
“S,” you laughed, pulling her into a hug, “you just got married. You don’t have to play matchmaker tonight.”
She grinned, pressing a kiss to your cheek. “Don’t worry. It’s not a guy. You and Harry are sickeningly perfect. I wouldn’t dare.”
You raised an eyebrow, letting her take your hand as she led you across the rooftop, pausing to say hello here, to accept congratulations there. But you quickly realized she was on a mission. Her direction didn’t waver. And when your eyes landed on the woman she was approaching, your breath caught somewhere in your chest.
Short, sharp white hair. A cerulean dress, striking in the soft light. A pale gray shawl wrapped delicately around her shoulders. In one hand, a pearl clutch; in the other, a champagne flute. Behind her, a younger woman stood just slightly too close, eyes alert and deferential.
Your mouth was suddenly very dry.
As you neared, the younger woman leaned in to whisper something into the older woman’s ear, but with a lifted hand, she was silenced without a glance, both sets of eyes already on you as you approached.
You reached out instinctively when she extended her hand, cool and precise.
“Ms. Priestly,” you breathed.
“This is my mom’s good friend, Miranda,” Serena announced with a sparkle in her voice, clearly proud of the introduction.
“The wedding is lovely, Serena,” Miranda said, her voice smooth and low and measured, the sort of tone that left no room for objection. “Absolutely beautiful.”
Serena beamed, thanked her, and turned to you. “She runs Runway as you know. I figured it was time you two were properly introduced.”
“I’ve heard all about you,” Miranda said, her gaze settling over you like a weight.
Your mouth parted, a faint breath catching as you tried not to choke. “Y-you have?”
She nodded, barely, her expression reading you like a book. Serena floated off before you could say anything else, leaving you standing alone in front of her.
“You’ve been quite the story lately,” Miranda murmured, sipping her champagne again when your hands fell away from each other. The way she said it wasn’t cruel like the others, more like an assessment.
You could only nod, unsure what version of yourself she’d been told. The nudie plastered on TMZ? The walk in the park with the future mayor? Your boyfriend who was double your age?
“I personally think Vogue shot themselves in the foot,” she said casually, her voice almost wistful in its cool indifference, “wasting an opportunity like that. A pity, but not surprising.”
You opened your mouth, but only a half-formed sentence came out. “I—well, I mean, Anna—”
She held up her glass slightly, as if dismissing the thought. “We’re photographing our summer line…oh, what is it? Next week?” she said, eyes cutting to the woman behind her, clearly some sort of assistant, who gave a brisk nod. “You’d look stunning in that little pink tank top from Westwood— the one with the Marc Jacobs jeans. Yes, yes. You’d photograph beautifully.”
You blinked as the thoughts clogged together in your brain. She was offering you the front page spread of one of the most well known magazines in New York City. Vogue’s direct competitor, high above the limelight of the tabloids.
A smile played at the corners of her mouth, not with much warmth, but also, not mocking. Just amused by your slow realization.
“A thousand girls would kill for it.” she added when you didn’t reply.
Your chest fluttered, equal parts dread and thrill. “That sounds wonderful. Thank you, Miranda.”
“We can talk after,” she added, “about internships in marketing. You seem to have a knack for... visibility. I think you'd fit in just fine.”
The hand that touched the small of your back made you straighten at once. You didn’t have to look to know who it belonged to—the warmth, the steadiness, the smell of his fresh summer cologne… it all calmed the blood rushing in your ears. You reached out to Miranda again, trying to steady your smile as you shook her hand once more.
“Thank you, truly.”
Miranda turned toward Harry as you broke apart again. Her hand lifted to him, palm down, and Harry took it in his, bowing slightly to kiss her knuckles.
“And don’t you look dashing, Harry.”
“You look wonderful yourself,” he replied, his voice dipped in charm. “Talking work outside the office? Now, that doesn’t sound like you at all.”
“I know, I know,” she said, waving her hand as if swatting the idea away. Her smile now was effortless, practiced, gleaming. “No more talk of work. Enjoy the evening.”
And with that, she turned, gliding into the crowd as though the conversation had never happened at all.
You turned to Harry, eyes wide. “What did I miss?” he asked, handing you your martini. It was ice-cold and cloudy with olive juice. Just the way you liked it.
“She— I just… oh my god,” you whispered, the sound catching at the back of your throat before it pitched up into a breathless squeal.
He quickly pulled his own drink back from the danger zone. “Okay, okay,” he laughed, watching you bounce slightly in place. “Tell me.”
“She wants me on the cover for summer! I’m— I can’t even—!”
Harry grinned, full and proud. “That’s fantastic, hon. Seriously.”
You shook your head, amazed, bewildered, covering your mouth and biting back a grin. Overwhelmed, flustered, giddy. You took a sip of the martini just to cool yourself down. It was perfect.
You shook your head, wide-eyed. “I can’t believe it.”
“I can.” His tone was low and easy, his answer immediate. You glanced up at him. He was already watching you, sipping his drink — tequila over ice, as always, clean and sharp.
“She sees the potential they were too short-sighted to notice. She’d be an idiot not to take you.”
Your smile widened. His eyes flicked down to your mouth. He smiled too.
And for a moment, you forgot you were ever annoyed at him at all.
After the speeches and the toasts, the first dances and the photographs, dinner was finally in full swing—and by the time you were sitting at the table with your family, you were ready for the night to end almost as soon as it began.
The ballroom glittered, cast in candlelight and soft music, polished silverware catching the glow like stars scattered across the table. You sat stiffly, your napkin folded in your lap and untouched. The scent of truffle and butter hung in the air, but you hadn’t taken more than a bite. Every word from your mother seemed to land like glass in your wine, dissolving whatever excitement from the afternoon.
She was on her third glass of champagne and already simpering and sentimental, her voice syrupy with nostalgia.
“It’s a shame you and Nate don’t see each other more often. Remember that summer in Portofino?”
Your fork paused midair. “Mom,” you hissed, sharp and low, heat crawling up your neck, but she didn’t flinch.
“I just think he’s such a wonderful young man. They made the most beautiful couple, don’t you think, darling?” She turned to your father, who was still chewing a piece of bread, eyes bouncing from you to Harry and back again.
“He always had such a good head on his shoulders. Thoughtful, kind, came from a solid family.” Her gaze flicked briefly toward Harry, then back to her plate. “Rare combination these days.”
“Jesus Christ,” you muttered, “Can we not do this?”
“I’m just saying,” she replied smoothly, reaching for her champagne, “we should see what the Archibalds are up to when we’re in the Hamptons. I’m sure Nate would be delighted to catch up.”
“Harry and I—“ you began, but you were cut off but a very low, even voice beside you.
“I happen to think your daughter’s perfectly capable of deciding who she wants to spend her time with,” Harry said, his eyes flicking up to look at her.
“Yes,” she replied after a pause, her voice dipped and cold, “that’s what I’m afraid of.”
Silence settled instantly over the table. You looked at your father, quiet as ever, ignoring whatever was festering beside him. Then your mother. Her smile had disappeared, her jaw tight. No one said another word.
You pushed back your chair and got up, the movement sharp. You didn’t look at anyone as you left, heading for the double doors—but then stopped short when you spotted Blair, alone at a side table with an empty chair beside her.
“Seen Chuck?” you asked, leaning down on your palms against the seat.
She hardly even looked up. “Yes, unfortunately. Out on the terrace,” she muttered, raising her flute. “He’s in one of those moods again.”
You glanced toward the open wall of glass, saw the shadowed figure just past the doors, and gave her a silent nod of thanks.
Outside, the city air met you like an exhale. Cool and welcome against your skin, the kind of air that felt private. You drew in a deep breath. Then another.
“You’ve seen better days, sis.”
Chuck’s voice floated from the shadows. He stood leaning against the far wall, a thin curl of smoke rising from his lips, the sweet, herbal scent reaching your nose. His tie was loose around his neck and sleeves bunched at the elbows. As unreadable as ever.
You walked over without a word. He passed you the burning joint from his fingers, and you took it. The two of you stood shoulder to shoulder against the cool cement wall in silence, sharing the stick, trading quiet between drags. The party buzzed faintly behind you, distant music and laughter bleeding out from the closed glass doors, but it felt far away.
“What’re you doing out here?” you asked after a moment.
Chuck’s eyes flicked to yours, then back out to the skyline. “Hate being around all of them.”
“Mom and Dad?”
“Mom and Dad.” he echoed, nodding, “Everyone. All the usual suspects.” He took another drag. “They show up to these things just to remind each other they still matter. Comment on who is wearing what, whose mistress is fucking who.”
You huffed a small laugh, your arms folding across your chest.
“The rest of the world isn’t like this, you know.” His tone softened, like something else was brewing beneath the surface. “When you step outside of it—it’s almost embarrassing how small it all seems.”
You looked at him, but his eyes weren’t on you. They were out past the buildings, far away. Somewhere you hadn’t seen him go.
“I didn’t get it at first. Not when…” He stopped and swallowed. “Not back then. But once I put some distance between myself and the circus, it changed everything.”
He passed the stick back. You took it without speaking, your brows knit as you pulled on it.
“It can happen for you too,” he said, quieter this time, “You gotta get out of that house.”
You turned your head to look at him, and now he was looking at you. There was a sharpness in his features tonight, something sculpted and hard in the clench of his jaw, and it made the softer things about him—the way he had your mother’s downturned mouth, the crease between his brows—feel almost tender by contrast.
You opened your mouth, unsure what would come out, some flicker of reply caught in your throat. But before you could speak, Chuck’s eyes shifted behind you, and you heard the music increase in crescendo before quieting again, footsteps approaching. Turning towards the noise, you saw Harry, his black suit jacket gone, his tie snug around his throat, sleeves pushed up in neat cuffs as he joined you. His eyes were on you, only briefly flicking to your brother to give him a short nod in greeting.
“Well,” Chuck exhaled dramatically, pushing off the wall, “Best leave you two lovebirds to it— don’t do anything I wouldn’t do, sis.” he said, as if forcing his usual humor. But it was dry, borne of saying what was expected of him.
“That doesn't leave me a lot of options.” you called after him quietly in hopes to lighten his mood, and as he pulled the door open with a whisper, the music inside flooding the night air, he turned and smiled at you before disappearing inside.
You smiled to yourself as you took another hit from the joint, eyes facing the cement at your feet before Harry stepped forward, taking it from your hand. You expected him to drop it to the floor, to step on it with the ball of his leather Tom Ford shoes. But instead, he brought it to his lips, sucking on the stick, the tip aglow in the night.
When he exhaled, the plume of smoke escaping his lungs, he merely said, “just at parties.”
You huffed a disbelieving laugh, shrugging without a word, rubbing your palms on your chilly arms.
A few moments passed, him taking a drag here and there, eyes out on the city, back at you, at his feet. He shifted around a lot, almost…nervous. You weren’t sure you’d seen him so uncertain before.
“I shouldn’t have said anything to your mother.” he said quietly, “That wasn’t my place.”
You tilted your head, searching his face. “No, don’t be sorry.” his eyes lifted to meet yours in the dark, “Sometimes I just…I get so overwhelmed by her. Always deciding things for me. And I forget I have a say in it. So…” you sighed, licking your cotton lips, “if anything, it was nice. For you to do that. To…stand up for me, I guess. So, thanks.”
He licked his lips, passing you back the joint as she shook his head, “It’s alright, I don’t need… I just couldn’t stand watching it happen. Flaunting your history in front of someone who is supposed to be your partner. Felt…”
“...wrong.” you finished. His eyes searched yours, chocolate and molasses all warm and inviting against the night sky behind.
He nodded, sighing.
“Do you want to go to the after party?” he said, veering the conversation, “It’ll be at the Ritz Car—”
“Why did you kiss me?”
The question split through the quiet like a snapped string. The music dulled while someone was announcing the cake cutting in a muffled mic. The cars below stopped their honking, your breath caught in your lungs. You don’t know what made you say it, but it was there, on the tip of your tongue all night, behind your teeth, waiting. And now, with your brain up in the clouds and your thoughts swirling like a drain, it was hard to bite it back.
“We have to talk about it,” you continued when he didn’t say anything. It was like he’d been carved from stone, so still, so…serious.
“According to the contract that you wrote—”
“—my lawyer wrote—”
“—that you wrote—” you said again, firmer, “we legally have to talk about it.”
He was still silent, his eyes glossy and beginning to squint from the high spinning his brain into cotton.
“Why would you write it knowing your feelings?” you asked softly.
Now, he was quick to reply.
“I don’t have feelings,” a long pause, “for you.”
You ignored the knife in your throat, the twist of it as the last two words dug it deeper.
“So…what was it, then? Just pretending?”
He didn’t answer right away. Just stared, those dark eyes so infuriatingly unreadable, jaw working, tongue wetting the corner of his mouth like he was holding something back, deciding whether or not to speak the truth of it into existence.
“Isn’t that what we’re doing?” he finally said, voice low and stern like iron. “Pretending?”
You looked away, tongue darting across your lips. You tried to force a laugh, something dry and bitter, anything to keep this from tipping over the edge. But it came out closer to a choke.
“Yeah,” you said, voice flat. “Right.”
He started to murmur your name, but you didn’t let him finish, instead saying: “I wanna go to the afterparty.”
“Okay.” he nodded after a long pause.
You turned toward the door. One step forward, you could do that right now. Swallow the thick lump in your throat and just focus on your steps. Another step closer to the door, to the party. Back to the charade.
But your heel caught. The hem of your dress snagged, slinking silk and ill-placed luck, tangled just enough to knock you off balance. Your hand reached out, fingers grasping for the polished glass handle, but you missed. The world tipped and the breath in your chest stalled. In the space between one blink and the next, you were falling.
The concrete rushed up faster than you could react, knee slamming into it first with a sickening jolt, your palms scraping down to catch your fall, dress pooling around the bend of your hips and down your legs. Your face stopped just short of the pavement.
You heard Harry move before you felt him, the frantic scuff of his shoes across the concrete, the quick skid of his boots in urgency. He didn’t catch you before you hit the floor, but he was there by the time you started to shakily rise, his arms reaching out, steadying, warm fingers wrapping around one of your hands while the other pressed carefully against your waist, holding you upright.
“Are you okay?”
You didn’t answer right away. Your hands were trembling, the sting in your palms burning more than the tears in your eyes. You could feel the blood beginning to seep from your knee, the yellow dress turning patchy red when you looked down at where you hit the ground.
But when you were finally standing, something in you snapped. You wrenched yourself out of his hold like his touch burned.
“Leave me alone.” You hated how your voice cracked, how it made you sound small and girlish and soft. Hated the sting behind your eyes, the wobble in your bottom lip.
“I just—” you choked, then clenched your jaw hard to steady yourself. “I just need a minute, okay?”
You could feel the frustration pouring out of you, irrational and stupid and real. Because it wasn’t just the fall. It wasn’t just the scrape or the blood or the dress.
It was everything.
You felt ridiculous. Embarrassed. Humiliated by everything, everyone. You weren’t a girl anymore, but in that moment, you felt like one. Like a child dressed in grown up clothes, teetering in heels that didn’t quite fit, trying to play at being unbothered, only to end up crumpled on the sidewalk with bloodied knees and a knot in your throat.
Harry was still watching you, stunned, half reaching out again, but you didn’t give him the chance as you shoved the door open and slipped back inside.
Stepping out of the elevator and into the penthouse suite of the Ritz-Carlton, you were met with low lighting, mirrored ceilings, and the bass of a song vibrating against the glass walls. There were already too many people there. Serena sat straddling her new husband’s lap on the velvet settee in the corner, laughing loudly, her heels kicked off and tossed somewhere nearby. Dan sat beneath her, suit jacket missing and looking at her like she was a dream, eyes half-lidded, lips parted, stoned or maybe just happy, and she leaned into it, white bubble party dress she’d changed into riding up high on her thighs. Somewhere across the room, Chuck was draped across a blonde in black sequins—her mouth grazing his throat in a way that seemed performative, like he knew people were watching. You scanned for Blair, but couldn’t find her. They must’ve been off, no doubt broken up over something stupid once again. The ache in your knee pulsed softly beneath your dress even as your skin buzzed with the alcohol in your system.
Harry stood beside you, one hand resting lightly at your lower back, and you didn’t look at him. Hadn’t, really, since the conversation on the terrace. Not a word on the limo ride over either. The tension had crystallized between you into something fragile and bitter.
“Grabbing a drink,” you said, not looking at him, and didn’t wait for a response as you walked off.
You moved through the crowd like you were underwater, the din of voices and laughter blurring around the edges of your muddled, thickening thoughts. The kitchen had been transformed into a makeshift recovery station: catering trays laid out along with boxes of pizza, greasy cheeseburgers, still-warm fries in silver bowls. Someone had poured high-end tequila into Gatorade bottles. A tray of mini wine shooters sat melting in a glass basin of ice. You didn’t have to be some college kid to know a good hangover cure when you saw one.
You popped a few salty fries into your mouth, sipping wine from one of the plastic shooters. The dress itched, your knee still throbbed, your lips still tingled faintly from the way you’d bitten them to keep yourself from crying. You wanted to go home. You wanted to scream. You wanted—
“Hangover cures don’t discriminate,” said a voice just behind you, echoing your thoughts.
You turned slightly, though you knew who it was from his voice. Nate.
“Comfort food is comfort food,” you replied coolly, chewing slowly as your eyes scanned the crowd for Blair again. Still gone.
He moved closer, smiling with all his boyish charm, “You alright? What happened to your leg?”
You glanced down automatically to where your scraped knee was just visible where you held the dress bunched up. The yellow fabric stained darker where the skin was torn. Nate crouched before you like he was still someone you were supposed to marry someday, his fingers brushing against your calf with uninvited ease.
“It’s nothing,” you said, pulling back, but not harshly. “Just fell, I’m fine.”
He stood again, that slow, perfect Nate Archibald movement, as though nothing had changed since prep school. “I can get you something, if you need it.”
You didn’t respond. His presence, though not unkind, clawed at something inside you. Your mother’s voice rang in your head—Nate always struck me as someone who understood the difference between reputation and legacy—and your stomach turned. Before, being near him felt like nostalgia, but now it just felt like stepping into a mold someone else had carved out for you.
“You look like you’re on the hunt for something,” he tried again, lighter this time as he watched you search the trays of food. “What’re you looking for?”
You turned toward him, lips parting to answer, when another voice—lower, darker, just a few steps behind—offered instead:
“Chocolate.”
You froze, for a moment, your eyes threatening to roll, but you bit your cheek to compose yourself.
Harry stepped forward slowly, reaching for the small, wrapped piece of Dove chocolate with quiet precision. The foil glinted in the light as he pulled the foil. He looked so put together, even with his hair a little looser, a few more curls falling into his forehead, his tan skin glowing in the kitchen lights. Your gaze dropped to the chocolate in his hand, and without thinking, you plucked it from him with ease.
It melted slowly on your tongue, the sweetness a stark contrast to the tension building between the three of you. Harry’s eyes found Nate’s, expression unreadable.
“Harry Castillo,” he said, offering his hand in a way that seemed casual.
Nate gave him a once over before accepting. “Nate Archibald,” he replied. “Nice to meet you.”
“She’s told me a lot about you,” Harry said coolly, “Our future mayor.”
“Funny,” Nate murmured, smiling without warmth. “I’ve never heard a word.”
“Nate, this is my—” you started, the word catching in your throat, bitter from earlier, caught between what was real and what was performance.
“Boyfriend,” Harry finished, gaze still trained on Nate.
You swallowed hard, the chocolate thick on your tongue. You felt like you were watching a game you didn’t remember joining, being played with rules you couldn’t change. They still hadn’t let go of each other’s hands.
You were seconds from grabbing another chocolate and walking straight into traffic when Harry let go of Nate, and instead of letting it drop, it found your waist, pulling you in a little closer.
“Ready to go?” he asked quietly in your hair. And as much as you wanted to argue and wanted to give him a hard time, a million excuses stacked on your tongue: We just got here. I want to find Blair. I want to scream at you. I want— I want— I want—
“Yes,” you said, a breath of relief, and you turned to Nate with a small smile. “I’ll see you, Nate.”
“Leaving so soon?”
“Gotta get her home.” Harry said, casual on the surface, but there was something territorial tucked just beneath the words.
“Okay,” you said firmly, pushing your palm into Harry’s side, “Enough.” You chastised him quietly as he chuckled, arm wrapping around your shoulder.
Outside, the air was colder. You folded your arms tight across your chest, holding yourself together against the chill as Harry scanned the street for George in the town car. Without a word, he slipped out of his jacket and draped it around your shoulders, rubbing your arms once, twice, until you stopped shivering.
You looked up at him, your brain still a little fuzzy from everything.
“Sucks that you’re handsome,” you mumbled before you could stop yourself. Stupid head high, stupid wine shooter, making your brain lazy, your tongue too lax. Too willing to spill your honest thoughts.
He huffed a quiet laugh. “Does it?”
You nodded, slightly delayed, like your head was floating.
“Sorry about that, then,” he murmured with a smile on his face. You rolled your eyes.
He kept rubbing your arms until a pair of headlights swept across the sidewalk, casting long shadows against the hotel wall. Harry reached for the door handle as it came to a stop and ushered you inside.
He slid in beside you a moment later, and you exhaled a long, frayed breath as your body sank into the plush leather seat. Harry leaned forward, murmured something low to George, and the privacy shield rose without another word between the front and back seat. You leaned your head back and closed your eyes, unsure what to make of the night, but grateful—at the very least—to be gone from it.
Your eyes began to droop shut with the lull of the engine, the steady drive, and Harry was scrolling through his phone when his voice cut through the backseat.
“How’s the leg?”
You cracked an eye open, mouth tugging into a crooked smile with a sudden boldness. “Why don’t you see for yourself?”
You pulled your hurt leg up and dropped it across his lap.
He gave you a look, half-annoyed, half-something else, and slowly lifted the hem of your dress over your knee. The harsh red of the scrape caught the passing streetlight, glowing faintly in the dark cabin. His hand skimmed along your thigh, fingers brushing carefully around the raw skin like he was scrutinizing it.
You weren’t going to think about how good it felt. You weren’t going to ask him to keep going.
But he did anyway.
“Hurt?” he asked quietly, fingers tracing the back of your knee. Your skin raised in goosebumps.
“A little.”
He hummed, still staring at your leg, and pushed the dress just a little higher.
The wine buzz still curled in your bloodstream, softening everything. Your head felt heavy, your body loose. The night shimmered in the corner of your vision like heat rising off pavement.
Your lips twitched with a teasing glint. Whatever it was folding over you, giving you the confidence to push him just a little more—dark windows, city lights sliding past, his hand still warm on your thigh—it made you feel like you were leaning into something dangerous.
“You gonna kiss it better?”
Harry looked up at you through his lashes, the tension between you coiling tighter.
“Would you let me?” he asked, his voice quiet and serious.
You swallowed thickly. The alcohol had seemed to dull your good sense, the head high of your joint hours ago stripping the edge from your hesitation. Your legs didn’t move. Neither did his hand.
Your breath came slow. Measured.
“Thought we were only pretending?” you asked, only a whisper.
He nodded. You looked over to the front seat, but George was gone from view, the privacy shield up, protecting you.
Looking back at Harry, there was a darkness to his eyes suddenly.
“Is this part of the act too?” you asked, the ball of your foot nudging into the thickness blooming beneath his slacks, your voice caught somewhere between mockery and want.
“Careful,” he said, low and quiet, though his hand hadn’t moved from your thigh.
“Why?” you asked, blinking slowly, head tipped back against the seat. “What are you scared of?”
His hand slid a little higher up your thigh, until the tips of his fingers brushed the hidden slip under your dress. He didn’t look away when he answered.
“You tell me.”
The silence settled again, thick and heavy, lit only by the blinking of city lights slipping past the windows. You let your head loll toward him, a soft smile at the corner of your lips that you weren’t even sure was real.
“I’m not scared” you lied, but still a teasing lilt to the words, “Just don’t start something you can’t finish, is all.”
Harry didn’t smile back. His palm moved, intentional now, pressing against the outside of your thigh with slow, anchoring heat.
“I won’t,” he said simply.
“Will you kiss me again?”
“Are you asking permission or—?”
“I want you to kiss me again, Harry,” it was the truest thing you could’ve said.
And just like that, as if waiting for you just to say those words, he leaned in slowly, like he was giving you one last second to change your mind. His hand slid up your leg again, one resting around the back of your thigh, the other cupping the inner, more sensitive flesh just above your knee. He shifted closer, across the leather bench, until his thigh pressed firm under yours, your legs draped across against his.
His mouth met yours gently at first—like last time, like always—testing the waters with reverence. But the second your hands found his face, threading into his hair, tugging lightly as you tilted toward him, something shifted again. His mouth opened for you, deeper now, tasting you, taking you. You inhaled him, the scent of fresh linen, sandalwood, a hint of sweat from the night as your head spun, lips parting as his tongue slid against yours with sinful, practiced ease.
You let yourself give in. Let yourself melt into him. Let him touch you like he wanted to, as if he had every right to. His thick, broad hands roamed higher, fingers skimming the slope of your thigh, then up—higher still, until your dress began to bunch at your waist.
You let yourself forget, just for a minute, what any of it meant. What it would mean tomorrow. What it had meant an hour ago. You let the night blur into the sensation of the gentle rock of the car, the muted lights streaking by the tinted windows, the privacy of it all. The way his breath hitched when your fingers clutched his hair tighter when his fingers traced the cotton of your panties.
“Harry…” you whispered, unsure if it was a warning or an invitation.
He didn’t stop. He kissed your mouth again, gentle, and you felt his fingertips brushing between the fabric and your skin, just barely skimming there. You gasped against his mouth. His fingers stilled.
“Tell me to stop,” he murmured, lips ghosting your cheek, breath warm against your jaw, “And I will. I promise.”
You shook your head. That wasn’t what you wanted. You were warm and drunk and high and downright aching for him. Everything felt blurred and silken and easy, and the weight of his hand between your legs was the only thing that made sense. Harry kissed your neck, pushing your face with his cheek to reach more of your skin, and your breathless sigh turned into a choked moan as he moved the gusset of your panties to the side and pressed a finger against your bundle of nerves.
Fuck, you heard him whisper against your throat, his fingers slipping as he circled around the little button of arousal, shh, shh, he cooed as your hips twitched, your thighs tightening, don’t want George to hear, do you?
Your eyes squeezed shut. You pulled his face to yours, kissing him harder, messier, desperate. He leaned fully into you, his body covering yours, one of your legs folded high against your chest, the other dropped into the footwell of the town car, spread wide around the hand that worked you open.
The yellow silk of your dress bunched around your waist as he groaned into your mouth, pushing two fingers inside you.
“Oh—oh, ah!” you gasped, jaw going slack as he filled you, curling his fingers slow and deliberate. Harry licked into your mouth, kissed along the corner of your lips, your cheekbone, the shell of your ear.
“You feel so tight, honey,” he murmured, “Clenching around my fingers so good, how’s that feel, hm?”
“S–oh, god–so good, Harry,” you keened, a sob choking out of your throat as he curled his fingers.
“Yeah?”
He pulled away, looking at your face, mirroring your expression of pleasure and pain, furrowing his brow and pursing his lips, “What a good girl,” he cooed.
“You were so mean today,” you said suddenly, your thoughts so easily tumbling out now.
“I know, I know,” he murmured, kissing your lips quickly to stifle your cries of pleasure. “S’okay, baby, I’m gonna make it better.”
You clung to the collar of his shirt, his suit jacket slipping off your shoulders, lost somewhere behind you on the seat. “You’re so—so thick,”
“I know, princess, takin’ it so good, tell me, what about this, hm? How’s this?” he murmured, leaning in to kiss you or to quiet you, you weren’t sure, because at that moment he curled against your velvet walls to the perfect spot and you moaned.
“There she is, honey,” he whispered, maneuvering so his thumb brushed your little clit above, “Wanna see you come on my fingers, come on now, give it to me,”
He kissed you again, wet and open mouthed, tongue sliding with yours. Your body arched into him, his fingers dragging that slow, unbearable pleasure out of you, building it until it was nearly unbearable. Your breath hitched, your thighs began to shake, and you clamped down around his fingers, unable to hold back the sounds climbing your throat.
“Harry,” you gasped, and he groaned like it physically hurt him to hear you say his name like that.
“Come for me,” he murmured, voice like velvet. “Come for me, sweet girl.”
Your eyes rolled back as it hit sharp and unrelenting, your thighs clenching around his hand as you came with a cry you tried too late to muffle. His mouth found your neck again, murmuring soft praise against your skin while his fingers kept working you through it, so steady and measured and coaxing every last wave from you. You were gushing, pulsing around his fingers, your body betraying every feeling you'd tried to keep hidden.
He kissed your cheek. Then your temple. His fingers slowed gradually, drawing it out, until your body gave out, limp and boneless in the seat.
Only then did he ease his hand from between your legs, gentle as ever. He smoothed your underwear back into place with care, the same fingers now glistening faintly in the dark as he brought them to his lips to clean.
You startled at the sudden tapping of knuckles on the tinted car window, the realization dawning that the car had stopped moving minutes ago. The air around you still felt thick with heat, Harry’s body moving away, the silence taut and humming.
Another soft knock on the glass, followed by George’s measured tone filled the silence.
“Miss Montclair? We’re here.”
Chapter 10: Two Truths and a Lie
Summary:
The Hamptons feel less like a getaway and more like a storm brewing offshore. A summer house full of eyes, suffocating luncheons, and your parents’ relentless reminders of who they expect you to be. Nate’s charm fractures under pressure, revealing the strings behind his smile. Harry shows up just in time to pull you away from it all...until a second truth sends you running.
Chapter Text
It was funny, how small your life felt when you were this high above the ground. That was the allure of the tallest buildings in New York, after all—floating above the clouds, watching the city shrink beneath you. From up here, everything seemed so distant, so trivial, even fifteen floors above the chaos. The honking cars, the crowds weaving through intersections, the glare of screens and store signs…it all looked like some distant hum, a life that belonged to someone else. Everyone became ants scurrying through their routines. They called cabs, hailed Ubers, darted into bodegas. Lovers reunited on corners, strangers bumped shoulders and argued over parking spaces, kissed goodbye at red lights.
Through the perfectly clear floor-to-ceiling windows, you could see it all. And yet none of it could touch you up here. You felt disconnected from it all, more so than ever. Like something forgotten or paused. If you squinted, it was easy to pretend you weren’t a part of any of it. Like watching the earth from space, so far away that even people disappear.
“Well, what do you think?”
You turned. Your father strolled through the space with his usual measured stride, footsteps echoing against the freshly cleaned floors. His suit was just pressed, his watch gleaming beneath the cuff of his jacket. His hair was greyer than you remembered, his gait maybe a little slower too. The weight of the years that had caught up with him when you weren’t looking.
You wondered, briefly and guiltily, if any of that gray was your doing.
Looking around, you took in the stunning apartment. Pale cream walls, warm oak floors, seamless white quartz in the kitchen and gold hardware and a fridge disguised behind the freshly painted cabinets. It was still unfurnished, but already elegant. A thousand square feet, at least.
“Seventeen hundred square feet,” he corrected gently, as if reading your mind. “Madison Avenue, so you’ll be close to us. And a walk-in closet—or use the second bedroom for that, knowing you.”
That glint of playful affection in his eyes made you feel like things were almost normal again.
If only.
You smiled faintly. “It’s perfect.”
He raised a heavy iron key, dangling from a Montblanc fob. “It’s all yours, pumpkin.”
You knew this was coming. Knew, the second he invited you here, what this was.
“I—” Your voice caught. Your hand lifted instinctively, but just before your fingers brushed the key, they dropped back to your side. “I can’t accept this, Daddy.”
He frowned. “Of course you can.”
You turned back to the window. The sky was burning gold now, streaked with orange. “I just want to do it myself.” you said softly, nodding to yourself subconsciously, hands tucked beneath your arms across your chest, “You told me I needed to prove it to you that I could. And I need to believe I can… get here without you.”
“I’m just so proud of you.” he said softly. Your tender heart pulled at the way his voice dropped, “That internship at Runway—I never should’ve doubted you. Let me give you this. Please.”
You smiled at the glass, watery and fragile. “I know,” you whispered. “But I can’t.”
The key jingled softly as he dropped his hand. He stepped beside you, both of you staring out at the city, shoulders aligned.
Silence settled. A long, slow moment where you let yourself feel the weight of everything: the new job, the cover shoot, the thrill of being seen. Of being taken seriously. And yet, beneath it all, a hollowness you couldn’t name. Something tugging—no, wriggling—from inside you.
“I’d like Harry to stay with us at the villa next week,” your father said suddenly, casual as if it had just occurred to him.
Your stomach felt like it plummeted down all fifteen floors at the sound of his name. Because the last time you’d seen your fake boyfriend, you were scrambling your way out of his car, tugging your dress back into place with trembling fingers, practically falling onto the sidewalk in your rush to get away. You hadn’t called him. You’d ignored his texts. Hadn’t dared replay the look on his face when you left. Not since that night.
“Oh–” you choked, “you really don’t have to do all of that, I–he—well, I’m—”
“We’ve got the space. And your mother agrees. We’d rather have you both under one roof.” he said, and as if only to himself, he nodded, murmuring: “right under our noses.”
You didn’t respond. You weren’t sure you could.
He looked at you, his expression gentling. “There’s a reason your mother and I have raised our concerns over the past few weeks, pumpkin. It’s not just him. It’s his family.”
You rolled your eyes. Of course that would play a part. You’d known it from the beginning—it was part of the reason you’d chosen Harry in the first place. To rile them up. To twist the knife by following their rules just enough, while sticking it to them with the one person whose name alone might make them choke on their Chardonnay.
It had felt clever, once. Strategic.
But now…now it felt petty, so small, so them.
Stupid family businesses. Stupid power plays and shiny stock portfolios with behind-closed-door deals. You were tired of watching people shake hands over dinner while drawing knives behind their backs, of boardroom drama masquerading as family concern. Of hearing the word “reputation” passed around and expected to smile and sip your wine without having anything to retort. To think that, despite everything, they were still playing the same tired game.
Your father played with the key in his hand, throwing it in the air as he mulled something over, and caught it with a final nod as if his mind had been made up in the matter of that second. “I think it would put your mother at ease. Knowing you’re with us.”
You wanted to ask more, to ask what about him being in private equity had anything to do with your week in the hamptons, why he couldn’t just leave work in the city while you went to the beach. But the knot in your chest tightened, and all you managed was a quiet, “Okay.”
And as you both made your way for the door, he paused, pulling the key back out and placing it in your hand. “If you change your mind,” he said, “it’s here. Waiting.”
“Daddy, I told you—”
“I’ve already bought it.” His smile was soft. “Whether you rent it out, live in it, or leave it empty, it’s yours. I insist. I’m proud of the changes you’ve made.”
You didn’t feel changed. You felt like a disaster. A girl in designer heels, still stumbling through her own wreckage. A mess.
He walked out with a wave, answering his phone as the elevator doors opened. You stood there alone, apartment keys biting into your palm, staring after him.
On the way home, you called Blair for what felt like the fiftieth time that week. She’d been dodging you—her and Chuck alike—though the latter was expected. Blair, not so much. And when her chipper voicemail box sang its apologies again, you sighed, already dreading the sound of your own voice.
“B, I don’t know what’s going on with you, but please answer the phone. I’m sorry if Chuck was an asshole at Serena’s wedding, I cannot be held accountable for how that man acts, you know that. I’m sorry if… if I did anything.” You paused, swallowing, “Please call me. I want to talk to you. Okay, well…miss you, bye.”
You hung up and stared up at the city buildings as you walked past, your feet tired from the walk over. But you needed to get your mind off things. Your mind was abuzz with so many thoughts, each one layered with a different brand of noise. Every time you tried to quiet your mind by thinking of packing—bikinis, sandals, your Prada sunglasses, sunscreen, that Ralph Lauren tote with the stripes, your van cleef bracelet—a different one rose louder. Blair, your parents, the internship you’d start when you got back. Gossip Girl and TMZ and tabloids. And him. Always, maddeningly him. Harry fucking Castillo.
You knew you should text him. Or call him. Or at the very least ask what the hell the deal was with the Gossip Girl post showing him out with Lucy.
But then you remembered—you'd violated the contract too. You’d skipped an entire week’s worth of scheduled appearances, leaving him to fend for himself against press, paparazzi, and the questions buzzing about Lucy now back in the picture. Those stupid articles and letters and addendums felt useless now, but you’d hold fast. If Harry wanted to flirt and flaunt around with an ex…well, you had too.
You’d already ignored the very last rule in the contract anyway. All because your stupid heart couldn’t bear the thought of this ending so soon, so abruptly. Even if Harry refused to talk about his feelings—even if he acted like there were none to name—you were still holding on. Just a little longer.
And now, you couldn’t stop thinking about that night in the car. His mouth. His hands. The way he touched you like he meant any of it or that it mattered. That you mattered.
You needed to exercise him from your system. Whatever spell he had on you—it needed to be broken.
So, you did the only thing that ever worked when your thoughts got too loud: you booked a hot yoga class in your mom’s name, using her credits.
Sweat it out. Purge it clean.
“George, please do not tell Harry you came and got me,” you warned as you climbed out of the car the next morning, fresh-faced, limbs still heavy from lack of sleep.
“Have a lovely class, Miss Montclair,” he said dutifully, the loyal little soldier he was. Not very promising.
You tried not to think about it. You tried not to think about anything as you got into class, bent into new positions to wake up your body, the movement stirring your thoughts almost medicinally.
You wouldn't think of Harry or his filthy mouth or the way his voice went all low when he was whispering praise in the backseat of a car. Not his fingers or the fact that you’d said his name like it belonged to you. Not the way he’d looked at you afterward as he put those said fingers into his mouth, cleaning off your arousal. And his face after. His face as you’d clobbered out of the vehicle into the night air. You wouldn’t think of it.
You focused on your breath instead, sweat slicking your skin as you moved through the heat like you were burning something off. Maybe it was guilt. Maybe it was longing. Maybe it was just plain fucking rage.
Because he didn’t get to touch you like that if he didn’t feel something. He didn’t get to make you feel that way. Like you were wanted, like you were his. And for him just to turn around and act like nothing had happened. Like he didn’t care.
And you were so tired of pretending. So tired of playing girlfriend in public, of playing half stranger in private. You weren’t made for this kind of emotional compartmentalization. You never had been.
And as the class ended and you grabbed a plush towel to wipe the sweat from your face, stepping out into the air, skin flushed, heart beating clean, you thought to yourself: Maybe it’s fine. Maybe it’s better this way. You had a job now, an apartment you didn’t know what to do with. You didn’t need him to be part of it anymore. He surely didn’t need you much longer either.
But then your breath caught.
Because there he was. Leaning against the car, arms folded, posture too casual to be innocent. George stood beside him, looking deeply apologetic.
“Fuck,” you muttered under your breath.
Harry straightened when he saw you, standing, calling your name softly.
Yeah, no. You turned on your heel and started walking.
“Hey,” he called after you. “You’ve been avoiding me,” he added, and you realized just how quickly he caught up with you.
“No shit,” you muttered, quickening your pace in your Lululemon like you were training for a marathon.
“I’m sorry,” he said.
“Oh, you’re sorry?” you snapped, stopping just long enough to shoot him a venomous look. “That’s rich.”
“Yes. I am.” He caught up, his hand catching your arm and turning you with more force than expected. “I’m sorry for what happened. For…for…”
Your eyes narrowed at him.
“I didn’t mean to—” he began, voice faltering.
You couldn’t do this. You started moving again.
“Wait!” he called, trailing behind.
You ducked into your favorite juice bar and let the bell jingle above you. You stood in line, arms folded, jaw locked. Harry wasn’t one to make a scene in public, and you’d use that to your advantage.
He stepped in behind you, his voice quieter now. “I’m sorry for what happened last week, okay, sweetheart?”
The nickname sent a shiver down your spine, but you ignored it.
“Yeah, I am too,” you said, clipped, eyes still on the menu above. You moved up in line.
“No, you don’t understand.” He stepped closer, his hand lifted as though he wanted to brush your hair back from your still-sweat damp face. “I took advantage. I should’ve never… You were drunk, probably still high. I shouldn’t have touched you.”
Your head snapped toward him.
“That’s what you’re sorry for?”
His brows furrowed, confused. “Yes, of course I am. The way I acted when we got in the car and—”
“Don’t,” you interrupted, voice shaking as you squeezed your eyes shut for a moment, the memories threatening to flutter in your stomach. “Please don’t.”
You moved up again.
“I’m not mad at you for that, Harry.”
He blinked, like you’d just thrown him off balance.
And you realized, all at once, the plain truth of it.
“I’m not…even mad at you.” you whispered, and stood in front of the ordering line, getting your favorite green smoothie. The girl behind the counter didn’t seem to notice the tension between you, the way Harry rubbed his jaw like he was trying to ground himself. She looked at him expectantly. He shook his head, then pulled out his wallet anyway and handed over his card, sliding it toward her like it was muscle memory. A small gesture, but still enough to make your stomach turn. You fought the urge to roll your eyes. It was something you’d noticed he always did—tried to smooth things over with little actions when it was the words that were too slippery to grasp.
You found one of the small tables in the corner and sat down, your legs folding in on themselves, your spine curling in. As soon as you were seated, your elbows hit the table and your face dropped into your hands.
“Explain to me,” he said softly. “Please.”
You sat back in your seat. You couldn’t explain it to him. How could you? There were no words how you were feeling, so many drudged up thoughts and feelings that you knew he didn’t share. Or at least, he made it clear to you in the words he used that he never felt that way.
Because you hated how easily he broke through you. That you hated how he touched you like you were precious, only to deny the part of him that clearly wanted you. That you let yourself begin to feel things for a man who insisted on drawing the line and then crossing it, again and again.
You just shook your head and said quietly, “My dad wants you at the villa next week. With us.”
Harry’s brow furrowed, like he hadn’t expected that pivot. Still, he nodded, accepting the shift in topic. “Okay.”
“I don’t know what they expect,” you went on, trying to keep your voice even, detached. “But he wants us both there. Staying in their house. Is that something you’re comfortable with?”
Harry thought for a moment, leaning back, looking down at his watch—the watch you’d gifted him, you realized with a lump in your throat—and then found your eyes again, “Yes.”
You gave a small nod, eyes drifting to the counter just as your name was called. Harry stood, retrieving the smoothie before you could. He set it down in front of you like a peace offering. It was a small, tender gesture, so simple it almost hurt.
He was sweet, sometimes. And that was part of the problem.
“It’s definitely preferable over spending time at my beach house with my parents in tow,” he added lightly, trying to cut the tension.
“They all stay with you?” you asked, brow raised.
He nodded. “Peter, Charlotte too—Camilla when she’s back.”
Your heart skipped a beat at the name.
“Oh,” you murmured, your guard dropped just slightly. “How is she?”
Harry’s adam’s apple worked around something solid and thick in his throat. “Fine. She’s doing just fine,” he said, clearing his throat. “She’ll be joining us next week at some point.”
You took a sip of your smoothie, letting the chill steady you. Slowly, your shoulders began to sink, the ire draining from you as sustenance filled your stomach. The buzz of the juice bar became a kind of dull background hum. Just two people sitting across from each other again.
“I’m sorry,” you said, barely above a whisper. “For…ignoring you. For being difficult.”
Harry shook his head. “You’re not, and I understand. I acted—”
“I just wish you would tell me how you feel.”
He stilled at that. His dark eyes found yours, mouth parting like he wanted to say something, but didn’t know how to start. Finally, he said, low and rough, “I’m trying.”
You didn’t answer. Just looked away as the bell above the door jingled again, another couple stepping in, fresh and smiling and uncomplicated.
“I know you saw me with Lucy,” he said then. The words felt careful, intentional.
You turned back to him as he added:
“She’s just an old friend—”
“—Girlfriend,” you corrected, your voice sharper than you meant it to be.
“Yes,” he said simply, truthfully. “I don’t see her anymore. I wanted you to know that. It’s just…with all this—I didn’t know who to talk to.”
All this.
You wished he’d talked to you. That’s all you wanted, after all.
But then again, you’d been avoiding him, hadn’t you?
Suddenly your phone was buzzing.
You scoffed, scanning the juice bar like you could actually see who’d had the gall to tip off Gossip Girl while you were still sitting in the fucking room. It felt personal—violating, even. A hit while you were down. But all you saw were strangers: sipping smoothies, checking phones, oblivious. No camera flashes, no whispers. Just…normalcy.
It made you want to scream.
You grabbed your cup, suddenly sick to your stomach. The smoothie that was supposed to fix everything felt gluey in your hands, stupid and artificial. You stalked to the trash can and slammed it in, the thud of the bag inside louder than it needed to be. Still not loud enough.
Harry said your name, but you didn’t turn right away. You walked back to the table and stood, jaw clenched, breathing in through your nose, out through your mouth. You tried to count to five like your yoga instructor told you to, tried to center yourself—whatever the hell that meant. But all you could think was how tired you were. Of the show. The whispers. The watchers. The contract. And him.
“I will…” you said slowly, voice tight with the effort of keeping your composure, as you flipped your hair back, normal, be normal, “...see you in a few days, Harry.”
And then you walked out before the anger bubbled over and turned into something messier.
The drive to the beach house was exactly the same as it always was. Same view. Same dull weather. Same backseat silence in your parents’ long town car, your knees pulled up awkwardly while bags were stuffed into the trunk. One year your mother insisted on a second car just for the luggage, and your father responded the following year by buying a bigger car. Because he could. Because they were ridiculous.
They were always at odds, your parents. Always somehow aligned anyway, especially when it came to you. As if being hard to manage was a family pastime they could only agree on when you were the subject.
The closer you got, the more it felt like dread tightening in your throat. The luncheons. The curated brunches and perfectly planned dinners. The tea, the charity bullshit, the polite smiles. The White Party next week that loomed over it all. Nowhere to hide, not even for a minute. Except maybe the ocean.
By the time the house came into view—sprawling lawn, smug little hydrangeas blooming like it was some kind of welcome committee—you were halfway fantasizing about just walking straight into the water and not turning back. You smiled bitterly at the thought, forehead pressed against the glass.
The driver pulled up. You got out. The air smelled good, afterall. A welcome sea breeze inhaled and tension exhaled. Fine, whatever, it was nice.
You didn’t say anything as you went inside, leaving the house keepers to grab your bags. You didn’t need to say anything, to talk to your father as he asked about the wine deliveries and the groceries that were to have arrived the day prior. The house was exactly the same, anyway. You could’ve walked through it blindfolded.
You found your room on autopilot and had just started to head for the closet when your mother’s voice rang up from the kitchen like a siren sent from hell.
Something about lunch, something about Nate joining.
Because even here, nearly a hundred miles from home, you couldn’t escape it.
You let out a frustrated groan, nearly a growl with how you punched your fists down, how you stomped across the room to the dresser to throw it open. You dug through it quickly, picking whatever of last year’s bikinis that would suffice and tugged off your clothes to replace it with the suit and a sheer cover up.
You walked out, half feral, storming down the stairs like a woman possessed.
Out the side door. Onto the deck. Down the steps. Into the sand.
And as the wind caught your hair, the ocean roaring in your ears, you curled your toes into the beach like it might ground you, like it might keep you from screaming.
You picked up your sandals and started walking.
You’d showered before dinner, scrubbing the salt from your skin and raking a comb through your hair until it fell in soft waves around your shoulders. Your sundress was casual—white linen, simple—because your mother’s voice would rattle in your head if it wasn’t at least tasteful. A pair of gold earrings with little mascara, and just enough effort so you wouldn’t be accused of letting yourself go.
The dining room was stunning. Of course it was. Floor-to-ceiling glass doors lined the back wall, flung open to the terrace where a stiff breeze rolled in off the ocean. The air smelled like salt and rosemary, the sky was turning violet behind the pale green sea. A picture perfect backdrop that anyone would kill to enjoy if they weren’t waiting for the next jab to come across the table like clockwork.
And as if right on cue—
“Pity you didn’t join us for lunch, darling. Nate missed you.”
“I’m sure he did,” you said around a mouthful of salad to your mother, not bothering to look up.
You could feel her gaze burning you over the rim of her wine. “Why don’t you seem pleased that he came by?”
You set your fork down with a clatter. “I’ll tell you why, Mother.”
Folding your hands neatly on the table in front of you, you lifted your chin, eyes lifting across the candlelit spread. Your skin was buzzing, your mind full of too many thoughts, too many obligations and expectations, her simpering gestures of backhanded affection wringing your nerves.
“Because you bring him up every two seconds of my life. You talk about him like he’s my boyfriend—which he’s not, by the way. You act like he’s some long-lost love when we very much broke up in college, for very good reasons, mind you. And, last but not least, I have a fucking boyfriend.”
“Hey,” your father snapped, “watch your language when you’re talking to your mother.”
You turned on him without missing a beat. “You’re no better. You let her get away with this. It’s like you both want Nate to swoop in and push Harry out of the way. Like he’s going to ride in and claim your poor, lost little daughter and make her right again—for you.”
He opened his mouth, but your mother beat him to it.
“You know,” she said, voice rising sharply, “I thought after all this time without your credit cards and your store accounts and your drivers, you might’ve learned something about gratitude. But clearly you haven’t learned a goddamn thing.”
Your mouth dropped open.
“You’ve been difficult every step of the way while your father and I have done nothing but try to help you. And frankly? I’m tired of it.”
She threw down her napkin, standing with a sharp screech of her chair, a manicured finger pointing dead at your chest. Your face was burning.
“You will hear Nate out. And you will think very carefully about whether or not you want to be a part of this family. Because without your Amex and your name, sweetheart—you are nothing.”
She stormed out, heels clicking like gunshots on the polished wood floors. Your father stood silently, wiping his mouth with his napkin before throwing it down and following her out.
The candles flickered around you in the ocean breeze, the waves crashed in the distance.
And your appetite was gone.
The next day, you’d joined your family for the annual yacht ride around the bay—your mother’s favorite tradition, one she insisted on preserving no matter how unsteady the waters beneath your relationships had become. Your father had invited a few old friends, business associates you barely remembered the names of, and they milled about on the upper deck, martinis in hand and white collars unbuttoned in the breeze. The sun was high, gilding the ocean in streaks of silver and blue, and the champagne was already flowing.
You’d texted Blair before leaving the dock. No response. She and Chuck would be arriving in a few days, which filled you with equal parts comfort and dread. The two of them had been giving you a headache lately with their back and forth. Serena and her family were due soon after, and you could already feel the strain forming behind your eyes.
Harry had texted that morning. You’d read his text three times, blinking at the screen like it might change. Then you’d locked your phone and tucked it into your clutch, pretending the flutter low in your stomach hadn’t just betrayed you.
Now, you stood at the edge of the boat, a champagne flute dangling between your fingers, its rim damp from where your lips had rested. The wind tugged softly at the hem of your blue and white jumpsuit, the fabric light and bright against your sun-warmed skin. Your shoulders still tingled from too many hours under the sun the day before, and a few freckles had begun to bloom along your collarbone overnight. The ocean stretched wide in every direction, deep and endless and quiet—unlike the house, unlike your parents, unlike everything else.
“Hey, stranger,” a voice came behind you, soft and boyish and warm.
You turned. Nate stood there, all windswept and sun-kissed and grinning like he hadn’t aged a day since college. His hair was still that same honey-blond mess that tickled his cheeks, a little longer than most men would get away with, falling into his eyes the second the wind picked up. His dimple pushed into his cheek as he smiled at you.
You didn’t hate the sight of him. You never had, really. No matter how complicated it all got.
He lifted his glass and tapped it lightly against yours, the crystal ring sharp against the open sky.
“For a minute there,” he said, eyes crinkling as he looked out toward the water, “I thought you were going to spend the whole cruise pretending I wasn’t here.”
You brought your glass to your lips, hiding your smirk. “Don’t tempt me. It’s a long boat.”
He laughed, and he had the kind of laugh that softened things. That filled in the cracks, the way he always had. There’d never been a time when Nate wasn’t charming.
You stood in silence for a moment, both of you staring out at the horizon like it meant something. The sun was high in the afternoon sky, baking the boat and your skin.
“Blair and Chuck will be in rare form this week,” Nate said, still looking out. “Think we’ll make it through one dinner without one of them storming off?”
“I’d give it twenty minutes. Start the timer when the second they step out of the car.”
“Ten if there’s tequila involved.”
You smiled. It was easy, talking to him like this. It always had been. And maybe that was the problem too.
Conversation flowed. The kind that didn’t demand too much from you. He asked about Serena, about your trip to Paris last year, about your parents—though he already knew most of the answers. You slipped into the rhythm of it before you realized it was happening. The kind of talk that felt safe because it wasn’t trying to be anything more than familiar.
“Well,” you said at one point, glancing at him sideways, “it makes sense.”
“What does?”
“Why you’re becoming the next mayor. You’re good at this. Easy to talk to.”
He tilted his head a little, that same crooked grin working at his mouth. “Not sure that’s because of the campaign.”
“No?”
His blue eyes cut back to you, the color impossibly bright against the sunlit ocean. “I like talking to you.”
You looked down, your throat catching on the warmth in his voice. You weren’t used to people saying things so plainly. So sweetly.
“Listen, Nate…”
But he was already jumping in.
“I know things are weird right now,” he said quickly, his voice a little lower now, more serious. “But I think—look, I think we should talk. About us. About what we were. What we could be again.”
You blinked, stunned by the shift, the sudden edge to his tone. Not sharp yet, just purposeful. You could feel him pushing, just a little. And he looked so earnest. So sweet. That fringe falling back into his eyes, that dimple barely showing now. He was still the boy who kissed you on the steps outside the library sophomore year. Still the boy whose hand you’d held under the table when his parents started fighting again. Still the boy who smelled like sunscreen and beer and something like good intentions.
But that was the thing, wasn’t it?
He was sweet.
He was safe.
He was good on paper.
But love had to be on the table too.
“I don’t know.” You said softly, shaking your head as you took a sip of bubbles.
“Why do you act like we’re not a good match?” he asked suddenly, frustration creeping into his voice.
You blinked. “Because, Nate… I don’t…I don’t love you like I once did,” you said truthfully. “It’s different now. Harry is—”
“Please.” His smile vanished. “I can’t believe you’re bringing him into this.”
“Nate,” you said, startled by the sudden shift in him, “What’s going on with you? Why—?”
“He’s twice your age. And he’s got nothing to offer you. You think that’s going to last? He can’t give you what I can. I could give you everything. A ring, a family. You wouldn’t have to work again unless you wanted to. We’d have houses in Malibu and here in the Hamptons and home in New York, right by Central Park like you love. You’d never have to lift a finger. You could be First Lady one day if my campaign goes well.”
Your mouth parted, stunned.
“I don’t want that.” Your voice was quiet but steady.
He flinched. “God, why do you have to be so difficult?”
There it was.
That word.
That fucking word.
You scoffed, “Screw you, Nate.”
“I don’t get it,” he muttered, shaking his head as you stood. “I’ve done everything your parents asked. I’ve shown up, I’ve played the part. I’ve tried.”
Your brows knit. “What do you mean, asked?”
He hesitated, suddenly realizing what he’d said. He looked away out into the bay again.
You felt the shift, cold and swift, slicing through the warmth of the evening.
“What did you mean by that?” you demanded.
He rubbed the back of his neck, sheepish now. “Nothing.”
“Nate.”
“I just meant… it wasn’t like that, okay? It’s not like I didn’t want to see you. I did. But yeah—your dad might’ve… donated to my campaign if I… Well, he wanted us to spend time together again. Thought it might jog something.”
Your chest went tight. “He paid you?”
“I wouldn’t put it like that—”
“I would.”
He winced. “Look, I didn’t take it because of that. I took it because I wanted to see you. I thought maybe we could fix things. I thought maybe…” He trailed off, then tried again. “You were everything to me once. I thought that mattered.”
You stood, your movements stiff, the champagne glass clinking as you set it down.
“I want you gone, Nate. We get off his boat, you’re going home. And I don’t want to see you at the party next week. I don’t care what your excuse is. You’re sick, your dog died, I don’t care.”
He stood too, hands lifted like he could rewind it all. “Come on. Don’t do this.”
“Don’t follow me,” you warned, your voice low and shaking. “And don’t come near me again. Tell my dad it’s over. Because we are.”
Your skin burned for the rest of the yacht ride, the fire of it crawling over your shoulders and neck where yesterday’s sun had lingered too long, left you raw and tight-skinned. The backs of your thighs stuck to the slick seat cushions, and every gust of sea breeze felt colder than it should’ve—briny and sharp, like it was cutting straight through you, chilling your ribs from the inside out. Even with the sun still bright in the sky, your body had gone cold. Your stomach twisted, tight as wire, and eventually you stumbled down the narrow stairs, clutching the polished rail as you made your way to the bathroom where you retched into the sink, hands braced on either side of the porcelain.
The taste clung to you. Nate’s words clung worse.
You were so tired of everything being out of your hands. Of being chosen for. Of plans being drawn behind your back like blueprints to a life you never asked for. Of conversations had behind closed doors—what’s best for you, what you should be doing, who you should be with. You couldn’t keep swallowing it down anymore. And so, for the rest of the ride, you’d stayed alone at the bow of the boat, arms wrapped around your waist, hair snapping in the wind like a flag of surrender. You stared into the endless blue of the bay and begged the salt air to scrape your skin clean, to drown out every last voice echoing in your head.
By the time the yacht was back at the dock, your limbs felt numb, your eyes heavy. You weren’t sure if it was the seasickness or the fight or the shame of a plan being laid out for you and finding out a boy you once loved played a part in it. You just knew you needed out.
So you ran.
The second the ropes were thrown over the cleats, your sandals slapped the gangway, arms pumping at your sides, just needing to move, needing to outrun the last few hours.
But then you stopped dead.
At the top of the dock, leaned casual as anything against his car—his car, not the towncar with George, but his own black Mercedes that he must’ve driven all the way here by himself—was Harry.
Your heart skipped. Then tumbled end over end.
The early evening sun was behind him, casting long shadows on the wooden planks, and he looked soft in the light, his silhouette hazy at the edges like something you might’ve dreamed. His casual buttoned shirt was wrinkled at the sleeves, pushed up around his elbows and the top few buttons undone, exposing the edge of his collarbone, that familiar little hollow you sometimes thought of mouthing at in secret. His curls were loose but slightly glossy, like he’d half heartedly run mousse through them and then tousled it all away. And his eyes…molasses-dark and wide beneath the longest lashes you’d ever seen on a man, watching you with something like hope and something like worry and maybe even something like longing, too.
It felt like déjà vu. And yet…this time, you weren’t walking out of hot yoga simmering in your rage. You were frozen.
And three things became clear in an instant.
First: The contract. The image. You had been ignoring him, yes, but this was still your agreement. You had to smile. You had to walk into his arms and pretend none of the messy parts mattered—not for the press, not for your parents, not for the cameras you couldn’t see but always suspected were watching. It had to look like you were in love.
Second: You were angry, that was the truth. Mostly. Because you were furious with him for not saying what you knew he felt, for staying silent while you twisted in circles wondering if it was all in your head. He’d looked at you like it was something. He’d kissed you like it was too. He’d even held your face with those hands like you were precious. And still, he said nothing. The push and pull, the pretending like this was only business when you knew it wasn’t. When he looked at you like that and smiled like he missed you, and still insisted he didn’t.
And third—damn your heart: You missed him. You’d missed him more than you wanted to admit. Even in your silence, even in your anger, you had wished he would show up. Wished he would say something, anything. And now he was here, smiling that shy smile, waiting like he always did. Like he would.
So two out of three won. And before you could stop yourself, you were running again.
You barreled down the dock like a storm, the wood groaning under your footsteps, your hair whipping around your face, your jumpsuit catching the wind behind you. And when you reached him, you didn’t slow down. You leapt into his arms with the full weight of your exhaustion, your rage, your longing.
He caught you with a grunt, his back slamming against the car with the force of it, his hands gripping your waist instinctively, pulling you into him further. His chest rose and fell fast against yours, and he laughed softly in your ear as you wrapped around him like a lifeline.
You reached up to press your lips to his ear.
“Kiss me like you missed me, Harry,” you whispered.
And God, he listened.
His hand slid up your spine, fingers weaving into your hair as his mouth met yours, open and warm and tasting faintly of salt and summer and something sweeter underneath—like honey stirred into tea. He kissed you like he was breathing again after holding it in too long, his thumb brushed beneath your jaw, tilting your face just so, and the rest of the world blinked out around you.
The cold you’d carried all afternoon began to thaw in his arms, the trembling in your shoulders finally slowing. And somewhere deep inside your chest, a new thought bloomed hot and urgent.
You would make him see it.
Whatever walls he was hiding behind, whatever rules he thought he had to follow—you would shatter every one.
You would make him feel. Because if it was true, if Harry was truly a hopeless romantic, you would make him admit it.
When you pulled back, he let you go with one last brush of his thumb against your lower back. His gaze shifted behind you, and you turned just in time to see the small crowd approaching from the yacht. Nate. Your parents. Their coworkers. All of them descending in crisp linen and golden tans, eyes flicking toward the scene you’d made. The only one that kept his eyes averted as you glared back, was Nate. Good.
You straightened slightly, but didn’t move from Harry’s side. His arm stayed firm at your waist, his presence a quiet wall between you and the rest of the world.
Your father was the first to reach you. He extended a hand toward Harry, who took it with measured calm.
“We’re looking forward to having you at the villa this week, Harry.”
Harry gave a short nod, his voice smooth but cool. “I’m sure it will be… memorable.”
You huffed a soft laugh at that, barely catching it in your throat. Your chest, still sore from the pressure of the day, finally loosened enough to let some air in.
Your father’s eyes turned to you. “Coming home?”
The dock beneath your feet felt steadier now, but the idea of climbing back into a car with them made your skin prickle again.
“I’ll ride back with Harry,” you said, voice even.
There was a pause, a beat too long. But then your father gave a single nod and moved on, trailing your mother toward the waiting convoy of black cars.
You didn’t look at them again.
Instead, you turned toward Harry, who opened the car door for you like it was the most natural thing in the world. You slid into the passenger seat, the leather already warm from the sun, the scent of saltwater and his cologne curling in the air like something that might even feel like safety if you let it.
He rounded the hood and climbed in beside you, and as the door shut with a soft click, the outside world disappeared. It was quiet. The kind of quiet you didn’t realize you’d been starving for.
You looked over at him, your hand still buzzing from where he’d held it. “Memorable, huh?” you echoed, eyebrows raised.
Harry glanced at you sideways, a little smirk ghosting across his lips. “We’ll just have to wait and see.”
The smile you gave in return wasn’t quite full, but it was there, just quiet and lingering. You looked at him for a long moment, studying the soft curve of his mouth, the golden edges of his eyes in the late sun, how the teasing charm on his face began to slip. His mouth relaxed, the smirk gone, replaced by something closer to concern.
“You okay?” he asked, his voice lower now.
You nodded reflexively.
He didn’t seem to believe you as he slowly reached across the console, his hand moving with deliberate care. Your breath caught as his fingers brushed over yours where they rested limply in your lap. The contact was gentle, barely there, like he was afraid too much pressure might break whatever peace had been made between you in the last few minutes.
“You looked…” he began, searching your face. “Like something happened.”
The warmth that had begun to collect in your chest flickered out. The boat. Nate. The sting of it all rushed back up your throat like seawater.
You turned away from him, angling toward the window as you shook your head. “I don’t want to talk about it.”
He didn’t press. Just a soft, “Okay,” as he withdrew his hand and started the engine.
The car hummed to life, but neither of you moved to speak again. You stayed quiet, letting the silence fill the space between you. This kind of silence, you didn’t mind. Because it didn’t feel like absence. It felt like understanding.
As soon as Harry set his things down back at the house, you told him to meet you by the back door after you’d changed. When he found you a few minutes later, changed into something more pool friendly, you took his hand and led him out of the great glass doors, through the terraces that unfolded like chapters—dining tables scattered with posh little iron chairs, garden paths winding past citrus trees and lavender pots—until you reached the farthest edge of the estate. Just beyond the stone walkway, nestled against the hedges that separated your family’s property from the curve of private beach, the pool lay waiting.
It was quiet here. You could still hear the hush of waves and the distant murmur of conversation from the house behind you, but it all felt far away, like the world had dulled its edges for you. Sunlight slanted low across the water, casting ripples of green and blue against the striped lounge chairs and the pale linen umbrella that shaded them. A lavender and cream pool float bobbed gently at the edge, its reflection caught in the glassy surface.
“I just want to be away from them all for a little,” you said quietly, spreading your towel across the nearest lounger and letting your cover-up fall from your shoulders. The cotton caught the breeze for a second before pooling at your feet.
“I understand,” Harry said, voice low and even. He settled into the other chair beside you, setting his sunglasses and magazine on the small table between you. He’d changed into navy swim trunks and a loose-knit polo that skimmed his collarbones and made his arms look even broader. His skin looked golden in the sun.
You sat together like that for a while, letting the quiet grow around you. It was a silence you’d grown used to with him. Unburdened, unfilled. You didn’t need to explain yourself, didn’t need to press. Even with all the things unsaid between you, it felt easy just like this. Like maybe, for a few minutes, you didn’t need to have all the answers.
You flipped your Cosmopolitan closed with a soft sigh. The pages were hot beneath your fingers.
“So,” you said, pushing your sunglasses up the bridge of your nose. “I found out something truly enlightening today.”
Harry folded his magazine closed and looked towards you, his expression unreadable behind his lenses, but the crease between his brows gave him away. “Oh?”
“My father has been paying Nate,” you said flatly, “to steer me away from you.”
You couldn’t see the cogs behind his eyes turning, but you could tell he was letting that thought digest, mulling it over. Then, he just leaned back against the cushion and tilted his head slightly, lips parting like he’d been waiting for the punchline. “Suppose that explains a great deal.”
You looked down at your thighs, still faintly marked by the indentations of your towel. The silence started to stretch again.
“How did it make you feel?” he asked after a moment, voice low.
You blinked. The question was simple, but it landed like a stone in your stomach.
You weren’t sure what to say at first. How to explain the feeling of being constantly steered. Of having your life orchestrated down to the syllable, only to be left fumbling when the sheet music ran out.
“The same,” you said softly.
“About?”
“My parents. It’s like… like they have this whole blueprint for my life, you know?” You shifted your sunglasses up again, this time to rub at your eyes.
Harry didn’t interrupt, only waited, like he knew there was more.
“I saw this little girl yesterday on the beach,” you said, gaze still on the sky, your mind’s eye far away in memory, “She was so cute. Floaties, a sunhat that kept falling down over her face. She was so excited—running for the water, skipping across the sand. And then her mother ran up behind her and started scolding her. For getting her expensive swimsuit wet. For getting sand in her shoes.”
Harry made a quiet, understanding hum as he nodded, just listening, and you kept going. Finally given the space at last to let out all the thoughts you’d been stewing in on that stupid boat all afternoon.
Your throat went tighter, “Did you know,” you pivoted, “when I was in school, I wasn’t allowed to play any of the sports I wanted?” Harry was just looking at you, studying you. “My mom said only poor kids played team sports. That my choices were tennis and horseback riding. Expensive sports. I had an image to uphold and a reputation to proceed.” You shook your head, a thick laugh forced from your lungs, “Everyone else got to play soccer. Even Blair and Serena were on field hockey for a while.”
You looked at him, tears rolling now. You couldn't quite stop them.
“Everything about my life has been told to me, planned for me, step by step. I went to the college they wanted, got the degree they wanted. And then…after all of this…they just expected me to know how to handle my life without them guiding me. Set me loose when I graduated and thought I’d follow in the family footsteps. But I….I think I kind of…I got lost in it. In the sudden freedom I had.”
Harry was reaching for you now, but there was a sudden fluttering sound, the flashing of bulbs.
Your head snapped up, the rush of reality slamming into you. Somewhere beyond the hedges, just through the bunches of hydrangeas and tall bushes, you could see the cameras peeking through.
“Fuck,” you hissed, wiping the back of your hands over your wet cheeks. “How the hell did they even get access over here?”
You made to stand, already half out of the chair, but Harry caught your wrist.
“C’mere,” he said, gently.
You hesitated. But he opened his hand, palm-up, and waited.
You let him pull you into his lap, one knee slipping on either side of his, your body curling into his chest. You pressed your face into the soft knit of his shirt, and he just held you—arms wrapping around your back. His hand stroked a slow line down your spine, then up again. His mouth pressed to your temple, warm and steady.
“Don’t let them see you cry, honey,” he murmured. “They don’t deserve those tears. And neither do your parents. I’m sorry.”
When your breath finally evened, you pulled back slightly, looking down at him. Your reflection caught in his Prada sunglasses, warped slightly by the curve of the lens.
You slid them off and set them aside.
“Why don’t we give them something else to talk about instead?” you asked, a shy smile curling through the last of your tears.
Harry’s brows rose, amused now. “What did you have in mind?”
You huffed a small laugh, and he smiled back, his thumbs tracing slow circles on your bare skin as you dipped your head down, pressing your lips to his.
The kiss was wet with tears and summer heat, the salt of the ocean still lingering faintly on your lips. What started as something soft, bittersweet and tentative, quickly deepened under the crescendo of camera shutters in the air. You pushed into him harder, your tongue slipping past the seam of his mouth, tracing the swell of his upper lip until he gasped and let you in. His hands tightened around your hips, dragging you down against him, giving in like he’d been waiting all day for permission.
You kissed him harder, your fingers threading through the curls at the nape of his neck, your lap rolling instinctively against his. He let out a low groan, just as the sharp voice of a housekeeper rang out near the hedges, shouting at the paparazzi to move along.
You pulled back, suddenly breathless, watching the lenses retreat behind the bushes, disappearing into the sunlight.
Harry looked up at you, his mouth kiss-bitten, a dazed smile playing at the edges. “Think they got their shot?”
You gave a soft, disbelieving laugh, brushing a hand back through his hair. “If they didn’t, they’re useless.”
Then, your smile curled into something knowing. Your hips tilted just slightly, pressing down on the hardening line beneath your thighs. You bit your lip at the feeling of it—so close, just the thinnest layers of swimsuit between you.
“Looks to me like you enjoyed that, Harry,” you teased, your voice syrupy and light, but there was heat bubbling underneath it.
He chuckled, low and rough, fingers flexing gently at your waist. “I’m just a man, sweetheart.”
“Excuse me, Miss Montclair?” came a small voice, tentative but polite.
You turned, face going hot. It was Gloria — one of the housekeepers — short and stout with a crown of pale blonde curls and a sweet smile spread wide across her round cheeks. Her hands were clasped tightly in front of her, and she hesitated as her eyes flicked between the two of you... then dropped to where your laps connected before snapping quickly back up.
“Um—your father would like you both to be at dinner in an hour,” she said, cheeks turning blotchy pink. “I thought I’d just let you know. So you can go shower and get ready.”
“Thank you, Gloria,” you said quickly — polite but firm, giving her an easy out.
She nodded, grateful, and disappeared just as fast as she came.
You sighed, looking back down at him.
His smile had softened, the pads of his thumbs still skimming slow, grounding circles against your hips. “What do you want to do?”
“Honestly?”
He nodded, humming in assent.
“I want a gigantic, greasy pizza,” you said, voice a little hoarse from the leftover tears. “And I want to eat it by the ocean.”
You paused, then added, quieter: “And then I want to sneak in the back gate and not have to look at any of them for the rest of the night.”
Harry laughed, the sound full and warm as it shook through his chest and into you, making you bounce lightly in his lap.
“I think we can make that happen” he said.
A few hours later and a much fuller stomach, you strolled along the beach next to Harry, the sun dipping low behind the estate lined horizon, casting a golden glow across the waves. Your feet sank softly into the cooling sand with every step, the hush of the tide filling the quiet between you.
He was talking, still, about some work hiccup earlier with a portfolio company, something about a board call that didn’t go how he wanted.
“Honestly,” he muttered, glancing out at the water, “if I wanted to spend my week off babysitting the CFO of a failing skincare brand, I could’ve just stayed in the city.”
You gave him a look, amused. “That bad?”
“No, it’s just…” He trailed off, shaking his head. “He asked if he could delay layoffs another quarter because he’s ‘feeling optimistic’ about Q4. I said unless he’s planning to personally finance payroll, optimism doesn’t mean shit.”
You grinned, biting down a laugh.
“And of course my brother decided to chime in with some 'holistic' suggestion about team morale. As if that’s the problem.”
You laughed again, watching the way his jaw tensed slightly, the edge of annoyance softening the longer he talked.
“He says I take things too seriously. That I’m too clinical.” Harry glanced sideways at you. “But if I don’t take it seriously, we lose money. And I don’t really enjoy losing money.”
You tilted your head at him, amused, letting your eyes skim across his profile.
He glanced at you, eyes softening “This means nothing to you, does it?”
You laughed, a quiet little snort. “Not really.”
He stopped walking, his hand still holding yours, and looked at you for a long moment. His expression shifting with fondness.
“It’s all boring anyway.”
You shook your head, lips tugging into something soft. “I like hearing about your world. Really.”
But as you said it, you saw his molten chocolate eyes drop to your lips. His head tilted, beginning to dip toward you. It all felt so fucking romantic. Every girl’s dream: a quiet beach walk at sunset, your favorite greasy comfort food still warm in your belly, idle conversation with someone you could either talk to for hours or sit with in silence and be just as content.
But your brows furrowed as you remembered.
Harry Castillo was a hopeless romantic. But he wasn’t willing to admit his feelings. He didn’t trust you enough to let you hold them. And he sure as hell wasn’t willing to say any of it aloud.
You pulled your hand back fast, stepping away.
“No.” Your voice came out low, rough. “No, Harry.”
He opened his mouth to speak, surprise flickering across his features.
“You don’t get to keep doing this to me. Telling me you have no fucking feelings, then trying to kiss me. Fingering me in the back of your stupid fucking car. Hugging me while I cry. Coming to stay with me and my family. You don’t get to do all of that if you’re gonna keep pushing those feelings down. The ones I know you have but don’t have the balls to say out loud.”
Harry’s brows furrowed, his face hardening.
“Don’t,” you snapped, holding a hand up between you. “Don’t even say it—‘I don’t have feelings for you, Montclair.’” You mocked him in a low growl. “‘Does it matter what I feel about you, Montclair?’ Yes. Yes, it fucking does, Harry. Because you put in that stupid fucking contract that we were supposed to talk about these things.”
“What do you want me to say?” he asked quietly. Coldly.
“I want you to admit there’s something here!” you shouted. The sound of it felt too loud in the open air. Your skin burned. Your throat clenched. Everything about you was on fire.
“You know what?” You scoffed. “Just forget it. There’s only a few days left anyway, right?”
You started to turn when he caught your wrist.
“Stop.”
Your lip curled at where his fingers wrapped around your wrist. Your eyes stung. Your throat felt scraped raw as you held back another flood of tears.
“It’s not that—” he started, taking a breath. “I just don’t know how… or if it’s even possible for us to—For you to even— I feel so dumb,” he said softly. “And with Chuck involved, it makes things—”
“Chuck?” you cut in, confusion shoving the anger aside. “The hell does my brother have to do with any of this?”
He hesitated, his eyes widening, then narrowing. His head tilted slightly. “What do you mean?”
“What do I mean?” you echoed, your voice rising. “Why are you bringing Chuck into this? He has nothing to do with us.”
Harry’s eyes searched yours, something cautious flickering behind them.
“You really don’t know,” he said after a moment, like he was still processing it himself. “I thought… I thought everyone knew. At least our families. It’s why I drafted the article in the—I thought you knew.”
Your heart thudded. “Knew what?”
He didn’t look away from your eyes, watching you carefully as he said, quietly, “Chuck… he’s a Castillo.”
You stared at him for a long moment.
“Okay. No. Don’t try to twist this around because I’m mad at you,” you said, shaking your head, voice shaking right along with it. “Is this some desperate tactic to distract me? Really?”
“It’s not,” he cut you off, glancing around for any onlookers, his features very serious now, “I wasn’t sure why you’d agreed to all this in the beginning. Seeing that your brother and I…well, my half brother—”
You took a step back.
“No,” you said, firmer now. “Chuck is a Montclair. He’s always been a Montclair.”
Harry’s voice stayed low. Careful. “Your mom and my dad… they—Chuck was born before she married your father. That’s why—”
“No,” you said again, the word slipping out before you could stop it. “No one ever said that. He is my brother.”
“He is,” Harry said gently. “But not by blood. Not by your dad’s blood.”
Your breath caught. All at once, pieces that never made sense started aligning like teeth in a zipper: Chuck refusing to use the family name on certain documents. Skipping every Montclair Foundation gala. Never sitting at the head table. That one time, years ago, when you overheard a whisper about 'mistakes' and 'scandals' and thought it was just rich people gossip.
“I’m sorry, I thought you knew—I’m so sorry, honey—”
You were running.
Running from the waves, from the glow of the water, from the burn in your chest. Blood roared in your ears, in your lungs, as your feet hit the pavement, your breath breaking, tears streaming. This couldn’t be true. There was no way this was real. Chuck was your brother. A Montclair. Through and through.
No one ever made it seem like he wasn’t. Not until a few years ago, when he exiled himself—only showing up to events for his friends, never the family. He said it was because... he said...
The house came into view faster than you expected, and you bolted up the steps, through the front door, veering hard left.
Down the basement stairs. Toward the room that had always smelled like cigars and whiskey, expensive cologne and old playing cards.
You threw open the heavy door.
And stopped dead in your tracks.
Chuck, Mr. Castillo, and your father. Like the start of an awful, terrible joke.
All seated together in a booth.
Chapter 11: Confessions of a Castillo
Summary:
Secrets come undone when the truth finally hits the table, leaving you reeling and unable to get out of bed for days. Late one night, a quiet exchange sheds new light on the story you’ve been told.
Notes:
warning: mention of ED later in chapter (not fmc)
Chapter Text
It was your father who spoke first.
“Pumpkin, what’s going on? Are you o—”
“Here’s what’s going to happen,” you cut in, your voice low and shaking with fury as you marched to their table. The three men hardly looked rattled. Chuck leaned back with a burrowed brow and twisted mouth, not even looking up at you. Your father’s surprise curdled into sternness. Sr. Castillo showed almost nothing at all, just the faintest crease between his brows.
“You’re going to tell me every ounce of truth you’ve got.” You jabbed your finger down at the circular wooden table, where their sweating cocktail glasses ringed the grain. The light was dim, casting deep shadows on their face. “Starting with why I’m only just finding out you’re not even my full brother.” Your hand snapped up, finger aimed straight at Chuck’s face.
Chuck’s brown eyes finally met yours. Your father blanched. Sr. Castillo’s mouth curved into a small frown.
There was a long, heavy pause.
“Sit down, Miss Montclair,” the eldest Castillo said with a sigh, almost gentle.
“No thanks,” you bit out, heat rising in your chest, your teeth grinding in your jaw.
“Sit. Down.” Your father’s voice cracked like a whip, the sternest you’d ever heard it.
You glared at all three of them before striding to the next table. Gripping the back of a chair, and you dragged it across the hardwood, the scrape shrill as nails on a chalkboard. You hauled it in front of them and dropped into it with a huff.
Both Sr. Castillo and your father looked to Chuck. He exhaled slowly, like it was all inevitable, then slid out of the booth. At the bar, he grabbed a crystal decanter of amber liquor, reached for a small glass, and carried both back to the table. Setting the glass in front of you, he arched a brow.
“I don’t want—” you began, defiant.
“Trust me. You will.” Chuck poured a finger for you, more for himself, then eased back into his seat with the decanter in the center of the table. “Father, why don’t you start us off?” His mouth curled. “Mr. Castillo, I mean.”
Sr. Castillo didn’t even react to Chuck’s teasing. He just swirled his whiskey, studied it, then said, almost idly, “I met your mother when she was about your age. She had no money, came from a poor family, and was looking for work. I gave her a position at my company.” He shrugged, as if the story had long since dulled for him. “We spent too much time together, got carried away, that’s all.”
Your stomach curdled.
“You knocked her up and threw her on the streets,” your father said flatly. Rage glinted behind his calm.
Sr. Castillo waved a hand, dismissive. “If she would’ve told me—”
“She did tell you, you—” Your father sat straighter, jaw set, then stopped himself. He scrubbed a hand down his face before turning to you. “Your mother can tell you the full story. Best to leave it to her. Or else I might end the night with assault charges.”
Sr Castillo only chuckled, Chuck was smiling into his glass too.
“So...how did she…” you asked, confused by the timeline. “How did you end up with her after that? I’m only a couple years younger than Chuck.”
“I met her a few months along,” your father said. “You know that story. I was on my lunch break, running late, rushing to keep up with what my father left me of his company. I barreled into her at a coffee shop, spilled it all down her blouse. I insisted she let me replace it and fell in love with her right then. Coffee stains and all. Bump and all.” His hand rubbed at his forehead, self-soothing. You’d never seen him like this before, not just a father, or a CEO, but a man with a past. A man who’d fallen in love.
Chuck snorted. “How sweet.”
Your father shot a look at him before going on. “I took her in when she told me what happened. We married quickly, let everyone think it was a shotgun wedding. I didn’t care. I loved her. She gave birth to Chuck and I gave him my name. And then you came a few years later. No one the wiser.”
Your palms pressed into your clammy cheeks, elbows on the table. You stared at him, your voice a broken whisper. “This is insane.”
Your father nodded slowly. “Everything was fine for so long. We were able to keep the truth behind closed doors, keep everyone in the dark—”
“Even me,” you cut in darkly.
He didn’t argue. Just nodded again, his eyes heavier now.
“And then Camilla got herself in a situation,” Sr. Castillo grumbled, shaking his head. “We had a family meeting to smooth things over. To decide what was best.”
“Which is where you come in, sis.”
Your ears perked. You turned to Chuck.
“I happened to see you and Harry at the bar that night, as I was leaving.”
“You were there?” Your eyes narrowed. You tried to rewind the memory—martinis, the hum of voices, Harry sliding into the stool with his solemn brow, ordering himself his pick of poison, and then the moment he offered you a deal. A fake boyfriend, neat and simple. But he’d said it himself: it had been a family meeting that night. You just hadn’t realized family meant your own brother, too.
You pressed your fingers to your eyes, rubbed hard against the confusion. “So you were at this Castillo meeting? Deciding what to do with Camilla?”
“We needed to keep her out of the papers, off social media,” Sr. Castillo explained. “And make sure no one dug deeper into the family. Our past.”
Chuck swirled the liquor in his glass, looking pleased with himself. “And then I saw you and Harry, hand on his shoulder, all sweet and simpering like you do best. It got my Chuck senses tingling.”
“Chuck senses?” you huffed.
“Spidey senses, Chuck senses—same thing.” He smirked. “I texted Blair to check in on you. We weren’t exactly talking at the time, but now you know why.”
“And what exactly does that mean?”
“That our breakups weren’t because of some cosmic fate, sis. Blair was always pissed at me for keeping the truth from you. Every few months she’d cave, realize why we couldn’t tell you, but then she’d flip again. She didn't understand that you were a liability. That there was a chance you’d spill to Gossip Girl the first chance you got. And when you started seeing Harry? She said it had to be fake, a setup to help with Camilla. Said he wasn’t your type. She wanted me to come clean so you’d finally give into Nate’s pursuits.”
You rolled your eyes, but bile rose in your throat. Blair knowing. Blair knowing everything when you didn’t...it made your skin crawl. Everyone knew but you.
Chuck went on, unbothered. “It didn’t matter to me, though. My hunch was confirmed by your soft launch the next morning, and again at Serena’s bridal shower when she couldn’t keep her mouth shut. Not too hard to put together.”
You stared at him, ice sinking down your spine.
“I told the family,” Chuck continued, “but they said you were free to date whoever you wanted. That you and Harry had nothing to do with Camilla, nothing to do with protecting the name. But Blair and I saw it differently. You were the perfect cover. You wanted the spotlight? Fine. Better you than me.”
He tipped his glass toward you, like a toast. “So I kept feeding it. Knew you’d be at the Met Gala, didn’t know if Harry would show. And you know I don’t do the black tie philanthropy thing anymore. Got real tired of it. So I went to the afterparty instead. Harry had arrived before you, which was perfect. I saw the opportunity and I took it.”
“The…opportunity?” you asked, though the answer was already sinking in, and you whispered: “The bartender.”
Chuck’s smile was infuriating. “You’re catching on. Amazing what people will do for a crisp Benjamin.”
Your hands curled into fists on the table. “Why does any of this matter? We wanted Gossip Girl to see us, anyway.”
“It was helpful that you’d been plastered all over from your topless debacle, but I knew we had to keep the momentum up, that people might lose interest with how fast scandals cycle now. So I made sure I was there every step. Sending people I knew to snap photos and send to Gossip Girl, I had friends at TMZ and Murdoch’s papers plaster your pretty face all over Instagram and print. Keep you trending while also keeping Camilla and me out.”
“But it didn’t work all the time." you said, shaking your head, "Camilla still showed up in the headline, that one day after I saw Nate.”
Chuck shrugged. “Yeah, that was the one time we slipped up. As you know by now, Nate didn’t just happen to show up. Your father wanted him there. Thought maybe some nostalgic schoolboy charm would snap you back into line. You, being the eternally difficult child—his words, not mine—never went with the plan.”
You laughed, brittle. “Oh, please,” you shook your head, scoffing at the indignity of it, “I always went with the plan.” you looked at your father, “I’ve been following your life plan for me since I learned to walk. Sorry that I grew up.”
Your father’s eyes hardened just a fraction, but he didn’t correct you.
Chuck went on, “But you’re correct, Camilla’s nurse came forward with some gossip from the rehabilitation center, and we didn’t catch it in time. Whatever it was seemed juicier than your run in with Nate, only because of the headline. She didn’t give anything worthwhile after all. But everything collided. We needed to keep things neat and tidy again. A girl I’d been with the night before—don’t look at me like that, Blair and I were on a break again—sent me pictures of you and Harry over coffee—” he mimed signing in the air—“some contract, I presume? You need to be more careful about your meet up locations—and then kissing goodbye. But I paid her a good sum to keep her mouth shut about whatever it was you were signing, and Gossip Girl still got her blast of you two smooching.”
Your head shook, disbelief clawing at your throat. “But how? How did you even know where we’d be?”
“My son,” Sr. Castillo piped up smoothly, draining the last of his whiskey, “is predictable. His secretary keeps his calendar color-coded, updated by the hour. Whenever you two were scheduled to meet, I had it sent to me. Passed it along to Chuck.”
You leaned forward, gripping the sweating whiskey glass that your brother poured for you from the beginning, and swigged it down in one gulp, the burn welcome. “So… so you’ve been watching me like—like a marionette. Every choice, every move I thought I made—”
“Strings were already tied,” Chuck finished, unbothered.
You slammed your glass back onto the table. “Why? Why did any of this matter so much to you?”
“I thought you were doing it to get under my skin." Your father admitted, voice low, "That I was going to have to watch you make the same mistake your mother made. It’s why I got Nate involved. Thought, if anyone could, he would set your head straight.”
“I saw the same pattern I’d already lived through once. I wasn’t about to let another scandal drag my name through the dirt.” Sr. Castillo said with a dismissive shrug.
Chuck grinned. “And for me, it was simple. You were the perfect cover, as long as I kept the strings in my hands. I didn’t care why, I just cared that it worked. Until I realized Harry was starting to catch real feelings that night at the club.”
You sat back, arms crossed tight. “Feelings.”
Chuck's grin turned cheshire. “A man knows when another man’s gone soft, sis. It was written all over him. And you were getting close. Sooner or later he would’ve told you why he couldn’t actually be with you. That you share a brother, that history was repeating itself. But he was falling hard. No doubt.”
Heat crept into your cheeks, though you hated yourself for it.
“Luckily, the wedding was the next day. No phones, no evidence of Blair icing me out or you and Harry fighting outside” He smirked. “All neat and tidy.”
You wanted to crawl out of your skin.
Chuck leaned back. “Which leads us now. When's the gig up, by the way? Was Blair right all along?”
You gripped the edge of the table, knuckles white, ignoring his smug questions. “How…” Your voice cracked, and you swallowed hard. “How much does Harry know?”
For once, Chuck didn’t answer immediately. He set the glass down, turned it slow against the wood.
“Harry doesn’t play these games. He hates them. I think he hates me." his voice had gone low, losing all its swagger, "I think he saw his father having an affair with our mother and never wanted anything to do with me." you glanced over to the Sr. Castillo who was impossible to read, his deep dark eyes on your brother, "So, no, he was never part of it. He keeps his head down, sticks to business. That’s why he was so easy to use. Predictable. A schedule, a habit, a lunch or dinner date with you every week at. Reliable as clockwork. But no—he didn’t know. Not then. Not ever.”
Something in your chest cracked open, but you kept your composure. You wouldn't let them see you break, even after everything.
Chuck leaned back, studying you with something that almost looked like pity.
“Don’t look at me like that, sis. I didn’t make the rules. I just know how they work.” a sad little smile began creeping back onto his lips.
“I’m Chuck Castillo, after all.”
You didn’t leave your bed for the next two days. The curtains stayed drawn, the air in the room gone stale, heavy with salt from the sea and the faint perfume of a crumpled dress still abandoned over the chair. Time blurred into shadows shifting across the wall.
Gloria came by more than once, balancing trays with steaming coffee, buttered toast, your favorite pastries from the café down by the boardwalk. The smell drifted in warm and sweet, but you turned your face to the wall. You wouldn’t eat. You wouldn’t talk.
“Miss Montclair,” Gloria called softly, her knuckles rapping gently before she eased the door open. Her voice was careful, delicate.
You didn’t move. Your eyes were raw and swollen, lids so heavy it hurt to blink.
“Miss, Mr. Castillo is asking about you.” She stood at the edge of the bed, her weight dipping the mattress as she leaned down, bringing the faint scent of starch and lavender with her.
You didn’t answer at first. You pulled the covers tighter, as if the duvet could shield you from the sound of his name. But at the mention of Harry, your mind betrayed you.
You saw him again, clear as if he were still standing there on the beach: the way his face had crumpled when you’d turned and fled, how his hand lifted like he might stop you, only to fall back to his side. His mouth parted, but no words came, only that look in his eyes: stunned, wounded, searching for you even as you disappeared into the dark.
Your throat closed. “Please leave me alone, Gloria,” you whispered, sounding so small, muffled into the pillow.
Gloria lingered, sighing softly, her hand almost resting on your shoulder before she thought better of it. You heard the padding of her feet retreating towards the door. Leaving you alone with swollen eyes, the salt-sting of your tears, and the image of Harry’s face burned against the dark behind your lids.
Once night cloaked your room that evening, you decided you’d had enough of your own tears. The air felt heavy, damp with salt and memory, your sheets clinging with the sweat of restless hours. You pushed out of bed, silk shorts and tank whispering against your skin as you padded barefoot down the hall. The grandfather clock ticked in the dark, its hands marking one o’clock as you crossed the main hall.
In the kitchen, your hands moved before your mind caught up, tugging open cabinet doors, searching blindly. A groggy fog still clung to your head after a day spent horizontal, eyes raw and swollen. You trailed your fingertips along the shelves, across jars of pasta, spices lined like soldiers, boxes of cereal you had no appetite for. Your nose stung, your fingertip catching another tear before it could fall. Everything felt upside down, as if the floor had shifted and no one had warned you. You didn’t know what to believe anymore, what to trust. Everyone spoke in riddles, pulling strings you hadn’t seen. You were tired. You felt impossibly small. A child lost in a house that suddenly felt too big, too empty.
“If you’re looking for the chocolate, I’ve got it.”
The voice made your heart leap into your throat. You spun, pressing back against the tall oak cabinets, only to find your mother perched on the counter, her robe tied close around her waist, silvered hair soft around her shoulders.
“You scared me,” you hissed.
She only smiled, holding out a bar of dark chocolate like a peace offering.
Cautiously, you crossed the kitchen and climbed onto the island beside her, your legs dangling, toes brushing the cabinet doors. The bar was warm from her hand when you took it, and when you bit into it, the richness flooded your mouth, bittersweet and grounding. You hadn’t realized how starved you were until then.
“Guess it’s genetic,” you muttered around a mouthful, trying for lightness.
Your mother’s smile tilted, weary and tender. For a while, the only sound was the crack of chocolate breaking between your teeth, the hum of the refrigerator filling the silence.
“When you were little,” she said finally, “I used to hide all your Halloween candy.”
You scoffed softly. “I remember.”
“I didn’t want you to end up like me,” she said. “I was terrified you'd… struggle the way I did with food. With how you looked. With how people looked at you. I didn’t come from a family with cooks or meal plans. My mother never told me no, and I thought that was the problem. So I overcorrected.”
She sighed, glancing down at her hands.
“It was selfish. You would scream your head off and I’d pretend I was standing firm, but really, I just didn’t know how else to protect you. I was trying to control the one thing I could.”
“I would get so angry at you,” you said, voice quiet.
She smiled, the kind that held regret. “It was always my favorite and most feared time of year. That bucket of candy felt like it had a hold on both of us.”
There was a long pause, the chocolate melting slowly in your mouth.
Then, softly, she added, “I’m sorry. I didn’t realize until much later how much of my own fear I was projecting onto you. I thought I was protecting you. But I see now how wrong I was.”
“It’s my one vice now,” you said with a little smile around the candy bar, “this and Gucci shoes. I just can’t help myself.”
She smiled a little at that as you passed the chocolate bar back to her. She took a small bite, then sighed and handed it to you again.
“I’m sorry,” she said quietly.
“I know, Mom,” you whispered.
“I should’ve told you everything. I was just… so afraid.” Her voice wavered. “When I met Harold, it was all such a whirlwind. I thought it was love. I thought he was in love. That he’d leave his wife and we’d be together.”
Her eyes drifted to the stovetop, glazed over, focused on something far away. “But he was older. So much older. And I didn’t understand yet… how men like that could be.”
You reached an arm around her shoulders, and she leaned into it just slightly, like it had been years since anyone had held her without needing something in return.
“Then I got pregnant,” she continued, voice barely above a whisper, “and everything changed. He showed his true colors—kicked me out, blocked my calls. I never heard from him again.”
She paused to steady herself. “And your father… he found me when I was at my lowest. Alone and scared and pregnant. I knew my family would disown me for the pregnancy, for being with a married man too. But he was so good to me. Truly. I know you don’t always see it, but that man has more heart than anyone I’ve ever known. He took me in, pregnant with another man’s child, and never once treated Charles as anything less than his own.”
She sniffled, taking a tissue from her pocket. “But your brother always knew. Maybe not at first, but deep down, he felt it. There was a tension between them, something… chemical. Like two bulls in a ring, always clashing.”
Her voice broke, but she kept going. “And when we finally told him the truth, it was all he needed to start pulling away. He started using. and shut us all out. Everything we hoped for him, everything we built for him—he just walked away from it.”
You could feel her breath hitch beside you.
“I was terrified the same thing would happen with you. That if you found out, you’d spiral too. That I’d lose you both. So I held on too tight. Tried to control everything. And in doing that, I hurt you. I see that now. I’m so sorry, honey.”
She dabbed at her eyes again, the tissue trembling slightly in her fingers.
“It isn’t just that Harry is Harold’s son,” she said softly. “It was… everything. The way he carries himself. The way you talk about him like he’s untouchable.”
You stayed quiet, her words wrapping around something tender in your chest.
“He’s older,” she continued, her voice thinner now. “Just like Harold was with me. And I know how easy it is to confuse that kind of attention with love. To think you’re being chosen for who you are, when really—it’s about control. About power.”
She looked at you then, and it felt like she was seeing you for the first time in years, her eyes full of something raw and aching.
“I was scared, sweetheart. Scared you’d go down the same path. That he’d take advantage. That you’d wind up pregnant and alone, just like I was. That you’d wake up one day with everything you wanted pulled out from under you, and no one left to help you pick up the pieces.”
You felt her hand move to yours, tentative but firm.
“I wasn’t trying to punish you. I swear to you. But I see now… I was projecting. I let my own mistakes get in the way of trusting you. And I’m so sorry.”
You put the chocolate onto the counter and turned toward her, your knee brushing hers as you reached out. She came willingly, folding into your arms, her head dropping against your shoulder.
It felt strange at first—the two of you perched on the counter like children, clinging in your nightclothes. But then her arms wound tighter, and you felt the shake of her breath against your collarbone.
“I’m sorry, sweetheart,” she whispered, voice breaking. “For all of it. For the things I said, the things I tried to control. I hope you know I never meant any of it, not the way it sounded. I was only scared for you. Always scared.”
You pressed your cheek into her hair, the silver strands warm and soft against your skin. Your own tears slipped quietly, salt tracing the corner of your mouth. “I know, Mom,” you murmured. “I know.”
For a long moment you just stayed there, holding each other while the refrigerator hummed and the clock in the hall ticked away the silence. The kitchen felt suspended, like the rest of the world had gone still so you could finally just be mother and daughter, nothing more.
When at last you pulled back, your eyes still damp, you blinked… and froze.
Because standing in the doorway was Harry, bed-headed and rumpled, a dark t-shirt clinging to him, charcoal sweatpants hanging loose on his hips. His eyes were heavy, tired, and fixed on the two of you.
Your mother’s head turned, following your gaze. And for the first time, she smiled at Harry.
“Come in,” she said quietly, sliding down from the counter. “I’ll leave you two to talk.”
She brushed her hand over yours one last time before padding toward the hall, her robe trailing softly behind her, leaving you alone with him in the hush of the kitchen.
“Hi,” you said, your feet kicking idly. Childish, feeling caught.
“Hi,” he whispered as he came closer, stopping just short of the counter, like he wasn’t sure if he was welcome. His hair was mussed, his jaw shadowed with stubble, and he smelled faintly of sleep and the salt air drifting in from the ocean.
For a moment neither of you spoke.
“You should be sleeping,” you murmured, picking at the wrapper of the chocolate bar in your lap.
“I couldn’t,” he admitted. He tilted his head to try to meet your eye, but you just kept your gaze down on your hands. “Haven’t been able to since we last…since I…” he shook his head, “Are you okay?”
Your throat tightened, heel dragging against the cabinet door below you, and your words came out as a hoarse whisper. “I don’t even know.”
You could feel his burning gaze on you as he took a step back to lean on the counter opposite of you. “That’s okay, you don’t have to have the answers now.”
A long pause rented the air, the hum of the fridge the only thing between the valley of space between you until he closed it again, restless, stepping closer, the hem of his shirt brushing your knee as he stood beside you.
“Talk to me,” he said softly. “Please.”
Your body felt so heavy despite the hours you’d wasted in bed, every muscle aching with the kind of exhaustion that had nothing to do with the lack of sleep.
Eventually you looked up and studied his face in the dim kitchen light — the soft shadows along his jaw, the mussed hair falling over his forehead, and those eyes. Brown and wide, worn with fatigue, but still warm. Eyes that had always looked at you in a way that made your heart clench.
They found you now, those puppy dog eyes, unguarded, and you felt yourself falter. For a moment you just stared at each other, the silence drawing long and thin, like a thread pulled too tight.
Once, you’d believed you could make him see it. You believed you could make him feel it, make him say it all out loud. But now, with him standing here, you weren’t sure of anything. You didn’t know what lived behind his careful looks, or if there was anything at all. Pretending had gone on so long you couldn’t tell where the act ended and the truth began. Nothing made sense anymore, nothing felt like it meant...anything.
You smiled then, a small, sad thing that barely lifted your mouth. “There’s nothing to talk about.”
He tipped his head, pleading without words, and stepped a fraction closer. “There is.”
You shook your head. The motion felt like a small, stubborn defiance. “I don’t want to talk anymore.” You dragged a slow breath down your ribs and willed the burn from your throat, the sting of your eyes, focusing back on your hands in your lap, “I don’t want to hear how hard I am to be around.”
The words seemed to hang there. He didn’t move, but you could feel him watching you, something unreadable flickering in the pause. When he finally spoke, his voice was low and steady, “I never said you were.”
You were hardly listening, squeezing your burning eyes shut, your words coming out wet and throaty. ‘I can’t keep waiting for something that isn’t there. For you to finally admit what I already know you’ll deny.’”
You waited as he tried to form the right words, as if holding himself together like glass. He opened his mouth, closed it, and then tried again, softer. “I—”
But he didn’t finish. The pause was not clumsy; it was a choice. Something unspoken folded back in on him.
“Let’s just…” you slid from the counter, wiping your eyes, “let’s just get through the White Party tomorrow, and we can be done. Camilla will be home, my dad said he’d give me back my credit cards and my store credit and my driver and my life will…will go back to normal.” you rushed it all out, trying to breathe, forcing a smile onto your tear-streaked face, “You can be done with me. No need to worry about me acting out or being…” your throat felt like it was closing up, “being difficult.”
Harry said your name softly, shaking his head as his hand reached up to touch your arm, but you pulled away.
“It’s okay, Harry. Waiting for you has hurt worse than anything they’ve ever said about me. I can’t do it anymore.”
Chapter 12: She's All That
Summary:
The White Party sparkled with linen and champagne, but under all the shine things begin to unravel. By the evening, it's just you and Harry, the noise fading until there was only the two of you and the truth.
Notes:
warning! this chapter contains smut
second warning: this chapter contains talk of attempted suicide (not harry or reader)
third warning: if you plan on or haven't finished watching gossip girl, the Big Spoiler is in here
(See the end of the chapter for more notes.)
Chapter Text
When you saw Harry the next morning, it was at the breakfast table, chaos pressing in from every corner. Housekeepers hustled through the dining room with armfuls of flowers, drapery, and blindingly white linens. Your mother held her teacup aloft like a queen while barking instructions, her scrambled egg whites left cold on the plate, half eaten. Your father hid behind the wide spread of the paper, coffee cooling at his elbow. Chuck hunched over his espresso, dark circles carved beneath his eyes.
Harry sat across from you, phone in one hand, coffee in the other. He looked tired too, but his gaze kept straying back to you, a constant nuisance to the semblance of peace you were trying to achieve over your breakfast. You pushed food around your plate, refusing to meet his gaze for long.
“Gloria, the peonies belong on the tables outside, not in here,” your mother scolded, pointing sharply. “Dorota, throw that cloth away—I don’t want to see it again.”
The noise gave you cover. With her voice filling the room, no one else had to speak.
But soon, you’d had just about enough, and you pushed away from the table, leaving your untouched food: “Think I’ll go get ready.”
Harry looked up, standing and said, “Me too.”
You rolled your eyes, but didn’t argue.
The two of you moved together through the storm of staff. You did your best to ignore his hand that brushed against your back, guiding you around trays of glasses, lengths of white chiffon, the slam of doors.
Then the front door opened, and five men muscled through with a gleaming ice sculpture, Fortuna herself tilting precariously as they moved her through the frame. Harry pulled you out of the way just in time, your chest hitting his, your breath knocked loose as the statue passed inches from your shoulder.
Now pressed up against him at the bottom of the stairs, your heart jumped wildly in your chest. By the time the sculpture disappeared down the hall, you found yourself looking up at him, too close, too aware of your pulse that thudded in your ears. He smelled like musk, like sweat and coffee and—
You pulled away fast, starting up the stairs.
Harry called your name.
“What?” you asked, blanking your face into neutrality.
His hand rested against the mahogany railing, gleaming from a fresh polish. “Would you stop running from me?”
You scowled down at him. “I’m not running. I have to get ready. So do you. You stink like the gym.”
There was a spark in his eyes now, amusement breaking through the heaviness. He stepped up one stair closer.
You instinctively stepped one step back.
“See? Running every chance you get.”
You scoffed. “What are you trying to do here, Harry?”
His smile widened, showing teeth. “Make you smile.”
You gave him a flat look, “I’ll see you in a few hours,” you said, already turning and moving back up the stairs.
“See you then.”
You barely glanced back as you called, “I’ll be the one wearing white.”
The estate had been transformed into something out of a lifestyle spread with every inch of the backyard veiled in white. Billowing drapery caught the ocean breeze, balloon arches rose like pearly gates at the entrance, and every table gleamed with pressed linen and crystal stemware. Platters of oysters glistened on ice, servers swept past with trays of white wine spritzers, and your mother stood beneath the grand tent with a glass raised, speaking of the children’s hospital in Manhattan in an off the shoulder champagne-white silk gown. Guests nodded along, dazzling in their dresses, sharp white tuxedos, all of them tailored and styled for the occasion. An endless tide of perfection.
You smoothed the front of your white top, the linen pulled together by two loose knots at your chest, the only things holding it closed, and lifted your chin as if that could anchor you. Your long white pants shifted in the breeze, but no matter how carefully you folded yourself into the tableau, the hollowness clung. Everyone else seemed so sure of their place, while you drifted at the edge, untethered, watching the world move without you.
Your eyes caught him before you could stop them. Harry was across the yard, standing with a man who looked like an associate, his posture relaxed but assured, that easy charm settling over whoever had his attention. The late sun kissed his shoulders, the ivory of his suit glowing despite matching the crowd. He leaned in slightly as the man spoke, listening with the kind of patience that always amazed you. You knew you were looking too long, the noise of the party dimming, your glass sweating in your hand as if all that was left in the world was the line of his jaw and the way the salt air ruffled his hair. And just as that sixth sense must've been getting to him, that innate feeling of being watched tickling his neck, making his gaze shift towards you, someone sidled up beside you.
“You’re staring.”
The voice was sharp but amused, and you turned to see Blair, radiant in a sheath of white satin, her eyes big and brown, her ruby red lips a little sad as she looked at you. She slipped seamlessly into place beside you, a living reminder of another life, another version of yourself.
“Hey, B.” you said softly, looking away from her and into the crowd again.
You saw the pout she gave you out of the corner of your eye, “I’ve been avoiding you. I know. And before you say it—yes, I’m the worst best friend in the world. Maybe ever.”
You arched a brow, bringing your glass to your lips. Before you took a sip, you said, “That’s one way to put it.”
Her shoulders dropped, the sarcasm dissolving. “I wanted to tell you. Trust me that much. But it wasn’t my secret to spill. It was Chuck’s. And every time we fought, every time we broke up over it—that was why. I couldn’t stand keeping it from you, but I couldn’t betray him either. So I avoided you. I knew if I saw you now, with everything going on, I would spill. I couldn’t do that to him.”
The sting came all the same, sharp and familiar as you looked at her finally. “You don’t think I would’ve understood?” you asked.
Blair flinched. “You’re right. I should’ve trusted you. I just—” her hand fluttered, useless in the space between you, “—I didn’t want to lose both of you. You’re my best friend. He’s…well, he’s Chuck. And I was terrified of being stuck in the middle.”
You swallowed hard, your throat tight. “He told me everything, B. And all I could think was how long everyone else had known. How long I was the only one in the dark.”
Her eyes shone, wide and earnest, her red lips trembling at the corners as her mouth softened. “I’m sorry. I am so, so sorry. You didn’t deserve that. You deserved me choosing you.”
For a moment, neither of you moved. The music from the lawn party carried faintly on the breeze, laughter from strangers who had no idea that your entire world had shifted these past few days. Then Blair reached for your hand, tentative, her usual poise cracked wide open.
You let her take it.
“I hate that I hurt you,” she whispered. “More than I hate these tacky paper lanterns your mother insists on every year.”
A laugh broke out of you, watery and unwilling, and Blair’s face lit just a little. “There she is,” she teased, thumb brushing against your knuckles. “I missed you.”
The ache in your chest loosened. She had betrayed you, yes, but she was still Blair. Still the girl who knew how to make you laugh through tears, who knew every secret you’d ever buried. And maybe that counted for something. It had to.
“I missed you too,” you said, and when she pulled you into her arms, you let yourself sink into it, the smell of her Hermès perfume achingly familiar.
When you pulled away, she was still holding you, her hands resting in the crook of your arms, steadying you, studying your face with those sharp, narrowing brown eyes.
“I know that look,” you said with a wary smile. “What’re you up to?”
“I’m still trying to figure out how the hell you went full Anna Nicole.”
“Blair!”
“Oh, come on!” she rolled her eyes, “I knew it was fake from the start. We used to call old men who preyed on college girls pervs. And look at you now!”
“I’m not a college girl anymore. And besides, those weirdos were, like, alumni hanging around frat parties. Total pedos.”
A grin spread across her face, and suddenly it felt like slipping back into something familiar.
“Well, shit, Montclair, never thought I’d see the day,” she said.
“Blair!” you squealed again, smacking her arm, “Who even are you?” Blair Waldorf saying a curse word still felt like a rare celestial event—you remembered the last time had been eighth grade, when she’d called Mrs. Fowey a bitch.
She shook her head, letting out a little laugh as she looked at you fondly. You mirrored her look, happy to have your best friend again, but the longer you looked, the more your heart began to ache again.
“He’s a good man, B,” you said then, soft, as if admitting it out loud might change something. You looked across the lawn for a long moment, watching him talk and laugh with partygoers, “He doesn’t treat people like pawns, he doesn’t see me as a headline or a bargaining chip, at least…not anymore. He’s not like any of the other guys in our world with narcissist egos the size of Manhattan.”
Blair arched a brow, lips twitching. “Oh god, you are down bad.”
You rolled your eyes, but she was already laughing, finally letting you go. The two of you stood shoulder to shoulder, gazes sweeping the sea of white linen and silk.
“I’m so ready to go back home.” she grumbled after a little pause between you. “All this open air is fine for a weekend, but I miss the skyscrapers. And shopping.”
“Hear, hear,” you agreed, lifting your glass for another sip, only to pause when your eyes snagged on someone else walking up the stairs to the lawn.
In the crowd, surrounded by kids her age, walked a thin figure with dark hair and caramel skin, her chin tilted high above the slim white scarf wrapped neatly around her neck. Her dress was plain linen to the knees, sleeveless, unadorned, and somehow that made her seem even more effortless.
Camilla had arrived.
You watched from across the party as she stood with a small cluster of girls. At first it looked normal, a bunch of polite smiles, perfunctory chatter, but then the body language shifted. Shoulders squared, eyes narrowed across the group. Hands that had been brushing hair now tugged at it, fingers snagging at the scarf at her throat. Even with the band playing and champagne glasses clinking, you could feel the tension coil tight.
Blair clocked it too. “Well,” she murmured, slipping her arm through yours, “looks like the Junior Met Steps committee is holding court.”
You shot her a look but followed her across the lawn. As you neared, the argument rose above the music.
“Come on, Camilla,” one of the girls was saying, her tone syrup sweet with an edge. “Two months away and you won’t even tell us why?”
“What was it, coke? Pills? Both?” another snickered, fingers grazing Camilla’s arm.
“Didn’t know they admitted people for a White Claw overdose.”
“Or what? Did you go too far? Try the hard stuff and not tell us?”
Camilla’s voice was small, defensive. “No, it’s not like—”
“It’s not like you go to rehab for good grades, Cam, come on, tell us,”
But they were already circling, toying with her hair, snagging at the linen of her dress. One tugged too hard at the slim white scarf around her neck and it came loose, fluttering to the grass.
There was a collective gasp. The band faltered, then stopped. In an instant it felt like a movie. The crowd froze, staring, while Camilla clutched at the angry purple mark around her throat. People began to lift their phones and point them at her.
No, no, no, no.
You and Blair began to run as quickly as you could, you on her heels. The moment you were close enough, Blair was grabbing Camilla by her shoulders, the girl’s hands held up around her own neck to hide the marks she bore, as Blair pulled her through the lawn and into the house.
“B!” you said, looking around at all the phones pointing at you.
“Come on!” she yelled, hauling the teenage girl away.
You glared at the other young kids, hissing, pointing your finger out into the air, “Get the fuck out.” You caught the eye of Chuck, of your family, and then finally, Harry, before turning to run after your friend.
Blair didn’t slow until the three of you were through the double doors, down a side hall, into a darkened guest room. The blinds were drawn, muting the sound of the party. Camilla collapsed onto the bed, sobbing, clutching at Blair’s dress. Blair’s brown eyes found you at the door, sharp and wet at once.
“Those jerks,” she spat.
“Yeah, well, I know you’re only just getting started on our foul-mouthed career,” you said, sitting on the edge of the bed. “So I’ll say it: those motherfuckers.” You turned to Camilla. “Are you okay?”
Between hiccupped breaths, Camilla managed: “I thought…I thought if I came back it would be fine. That they wouldn’t care, that we'd all be okay and just ignore why I'd been gone. But they just kept asking and asking. Saying horrible things. Pulling at me like—” She broke off, burying her face in her hands.
Your phone vibrated in your pocket.
You stared at it, a realization coming to your mind. Gossip Girl was behind. It should’ve been posted right away about the marks, about her neck, about the true reason Camilla went to rehab in the first place. So Gossip Girl didn’t know yet.
Which meant there was still time…
“B…” you whispered, showing Blair your screen.
Camilla caught sight of it and gasped, "Oh god,"
"She's delayed," Blair said as if reading your mind, "We need something to keep her from posting anything else."
And then, with something sparking like fire in her eyes, she met your gaze.
“Do it,” she said.
Camilla sniffled between you, lifting her head just enough to look between you.
“Are you sure?” you whispered.
“Set him free,” Blair whispered, holding Camilla tighter.
You were on your feet before you’d fully decided, phone already to your ear as you left the room.
It only rang twice.
“Hello?”
“How’s Paris, Lonely Boy?” you said quickly.
“It’s… great, going well." he said a little suspiciously, "Would prefer to be enjoying it without interference but here we are,” there was gentle laugh, but when you didn’t chuckle back, he paused and then said. “...What’s going on?”
Through the receiver you caught a muffled second voice, feminine, curious. You could almost see the way her blue eyes would flicker, questioning, as she asked who it was.
“I have a proposition,” you said, forcing your tone steady.
There was a pause, longer this time, then the single word. “Okay…”
“Don’t post anything about Camilla.”
The silence that followed seemed to stretch into eternity, the muffled voice on the other end hissing again, a door closing somewhere far away before he returned.
“What do you mean?”
“Cut the shit. I know. I’ve known for a long time and never said anything. Now can we skip this part? Are you going to listen?”
Another pause, heavier this time before you heard his voice again, tighter. “Talk.”
“Don’t post about Camilla,” you repeated. “Not now, not ever.”
“And why,” he said slowly, “would I do that?”
“Because I’ve got something better for you,” you said, biting your lip. “If I give you this, you won't post about Camilla. You’re probably getting tips right now, but I want you to ignore them.”
He almost laughed, a short exhale. “Doesn’t sound like much of a deal to me.”
Your voice sharpened, the words like a blade in your mouth. “Oh? Should I hang up and tell your beautiful bride the truth? That the only reason you wormed your way into our lives all those years ago was by inventing a snarky little gossip column to get into her bed?”
The silence that followed was brutal. You could hear nothing but your own heart, pounding, each beat dragging your breath thinner and thinner.
Finally, at last, he spoke. “Fine.”
You exhaled, your chest trembling, the air leaving you all at once.
“This better be goddamn groundbreaking, Montclair.”
“Oh,” you said, your grip tightening on the phone. “It’s earth-shattering, Humphrey.”
You went back into the bedroom, your skin jittery, your stomach turning and your heart thundering so hard you felt it in your ears.
There were more people now. Peter and Charlotte had arrived, their presence filling the room with a strained quiet. Harry stood near the window with his arms folded, the sliver of light from the drawn curtains catching on the edge of his jaw. Camilla sat hunched on the bed, Blair beside her, holding out a handkerchief. The young girl's tears had slowed, but her face was blotchy, her hands twisting nervously in her lap.
You crossed the room and sat down on the other side of Camilla, the mattress dipping under your weight. She glanced at you briefly, her eyes glassy, before leaning back into Blair’s shoulder. For a moment you only sat there, one hand resting lightly on the blanket near hers, steadying yourself in the closeness of the two girls.
Peter crouched in front of his daughter. “This has gone on long enough,” he said, quiet but sharp. “You can’t keep carrying on like this. You need to pull yourself together.”
Camilla’s chin trembled. “I just want to go home,” she whispered.
Charlotte shifted beside him, her hands smoothing over her skirt. “You belong here with your family, darling, not hiding away.”
You leaned forward slightly, your voice softer, meant only for Camilla. “You can stay in here until the party is over. No one will bother you.”
Her eyes flicked toward you, brimming again, a small smile of thanks on her lips before she looked back to her lap. Her parents were already speaking over her, talking about appearances and strength, words that pressed heavy without touching what mattered.
Your phone buzzed in your pocket. You ignored it.
A sharper sound followed, Harry’s phone chirping from across the room. You lifted your head as he pulled it from his jacket, and he looked at the screen once and then stilled. When his eyes rose to meet yours, they were wide and unblinking.
Before you could move to answer or explain yourself, the door opened wide. Your parents swept in with Chuck on their heels, his tie loose, his chest rising like he’d run up the stairs. His gaze cut across the room—at Camilla, at Blair, at the cluster of parents—before landing on you. And when it did, the smallest smirk tugged at his mouth.
“Is everything all right in here?” your mother asked, already sliding to Charlotte’s side, hands gripping her shoulders as if she might crumble. Your father crossed to Peter, their voices hushed and urgent.
Chuck ignored them all, moving closer to you. He dipped his head, voice low but carrying. “Good job, sis. Can’t believe you beat me to it.” His hand flicked against your chin in a rare, almost affectionate gesture.
A shaky sigh escaped you before you stood and pulled him into a hug. For a moment, he held you tight, one hand firm at your back, a rare show of closeness that steadied you more than you expected.
“You’re not mad?” you whispered.
“No,” he whispered, and then, making your heart clench, he dipped his chin into your neck, lips at your hair as he said: “Thank you.”
When he pulled away, he turned to the room, smoothing his white tie with a flourish. “Well,” he said, his tone carrying, “it’s official now. The world knows I’m a Castillo. So what do you say? Shall we get this party really started for my grand coming out?”
The words landed like a dropped glass. Heads turned, and voices suddenly rose.
“Wait—what do you mean the world knows?” Peter snapped.
“Who leaked it?” Charlotte demanded, her face paling, "How? How could anyone find out?"
The room buzzed with panic, everyone talking at once, while Chuck only smirked, enjoying the chaos. And then the eyes turned on you.
Harry was still watching you from the window, phone in hand, waiting.
It would have been easy to stay silent. To let the confusion whirl around you, to let Chuck take the blame or keep the mystery alive. But you found yourself standing, spine straightening, chin high.
“I did it,” you said, "I sent it to Gossip Girl."
The room fractured. Voices crashed into each other, shouts and accusations.
“You little snake—” Charlotte spat.
“How dare you—” Peter started, eyes flashing.
But before their words could sink their teeth into you, you realized something happening that you hadn’t expected. Your parents’ voices were angry, unflinching, but...not at you, but at Peter and Charlotte.
“Don’t you dare speak to my daughter like that,” your mother snapped, pointing across the room.
“Keep your mouth shut about my family,” your father growled, “the way I’ve kept mine shut about yours.”
Charlotte reeled, clutching her pearls. “And what’s that supposed to mean?”
The uproar swelled, shouting, snarling, the whole room boiling over until Harry’s voice cut through it, sharp as steel.
“Enough.”
He stepped forward, placing himself squarely beside you, his presence cutting through the chaos. His voice was iron. “She's had more guts than all of you. I’d bet every cent to my name she did it to protect that little girl.” He pointed toward his niece. “Something none of you would do given the chance. You’d all rather throw her back to the wolves than protect her."
Silence fell like glass shattering.
Harry’s jaw set. He looked around the room, then back to you. “We’re leaving.”
Harry’s hand found yours as the room fell into dumbfound silence. You didn’t even remember walking away until you felt him guiding you, his grip steady at the small of your back. He pushed through the tangle of voices and bodies with quiet authority, ignoring your parents’ questions, ignoring Chuck’s arched brow. The next thing you knew you were out of the bedroom, down a narrow hallway, the murmur of the party a distant hum.
He opened a small side door and ushered you into the butler’s kitchen. It was cooler and dimmer in here, stainless steel gleaming under soft light, the smell of lemons and polish sharp in your nose. He shut the door behind you, the click loud in the quiet.
For a moment neither of you spoke. You were still trembling, your back to the counter, your fingers pressed flat against the edge of the sink like you might slip through the floor. Harry stood across from you, jaw tight, still catching his breath.
“What happened?” he asked finally, his voice low and gentle.
“I—” Your throat closed. “I couldn’t just let them—I didn’t want them to see her like that. Camilla, her–her neck.” You blinked fast, tears prickling your eyes, your voice shaking, “I can't believe, I thought—I mean, everyone thought—it was drugs, not...not that. Oh god, and those people…they’ll take anything they can, Harry. They take and take, and they don’t care who they destroy. She’s just a story to them. They’ll eat her alive.”
You were gasping for breath, your hand coming up to your throat as tears rushed down your face. God, would you ever stop crying?
He stepped closer, his hands coming up to frame your face. “Hey, look at me.” His voice had softened. “It’s okay. I’m not mad at you.”
Pressing your cheek into his palm, you clutched at Harry's wrist like it was the only thing holding you up. “I know I make everything worse,” you whispered, the words tumbling out. “I know I shouldn’t have. But they’re so cruel and she’s so young. I didn’t want her to—to suffer like... didn’t mean to be so...oh god—I’m so sorry, Harry.”
His thumb brushed your skin, slow and steady. “You’re not difficult,” he said, quietly filling in the word he’d known you’d say. “You’re not broken. You’re not… You're perfect.” His eyes searched yours, as if willing you to believe him.
But the words only made your throat tighten worse. “I am difficult, though,” you rasped, your fingers curling in the fabric of his sleeve. “Everyone sees it, everyone knows. They tell me any chance they can.”
He flinched at that, just barely, as though the thought of it cut deeper than he could show. “No,” he said, firmer now. “That’s what they want you to believe. But I see you. All of you.”
The silence pressed in again, broken only by your ragged breathing. You tried to look away, but his hand slid to the back of your neck, grounding you.
“Harry…” your voice cracked on his name, fragile, unsure.
“Listen to me. Listen," he insisted when you began to shake your head, "I didn’t understand… I didn’t know how to feel, how I really felt,” he went on, his forehead lowering until it nearly touched yours with a sigh. “I didn’t know what to call it, didn’t know if I was allowed to, with the way our families were. But I should've known what it was, and I should’ve told you. I should’ve said it every day since. I’m sorry.” His voice thinned, almost a whisper.
“I love you, sweetheart."
The words seemed to knock the air from your gut. A sob escaped, sharp and aching, as your tears blurred everything—his curls, the circles under his eyes, the softness of his gaze. But his hands stayed firm, steady, keeping you with him.
A throaty laugh suddenly broke through your tears, small and watery. “You’ve only been fake dating me for eight weeks, you weirdo. You can’t love me already.”
That earned the faintest smile from him, a quiet huff of laughter in his chest. His other hand slid from your cheek into your hair, so his fingers clung there like he couldn’t help anchoring himself to you. “It’s the easiest thing I’ve ever done,” he murmured, his gaze dropping to your lips before finding your eyes again. “Being with you, wanting you, loving you. It doesn’t feel fast. It just feels right.”
Before you could answer, his mouth was on yours. Gentle at first, a little brush, and then deeper, steadier as he pushed into you. His lips were so soft, the taste of salt from your tears on the soft pucker of his top lip. When he pulled back, his smile lingered. “All I want is to be around you. All the time. You've made me crazy these past two months."
Your hands clutched at his white suit, pulling him in again, kissing him harder. His hand dropped to wrap around your waist, warm and broad, spanning your back and hauling you flush against him. The lapels of his jacket bracketed your body, shutting out the rest of the world. Your tongue slid past his lips and he took it greedily, fingers tightening in your hair as he devoured you. He smelled like crisp linen and pine, like a clean summer morning after rain, and it was dizzying. He pushed you back into the counter, teeth catching your lower lip until you gasped, his groan vibrating against your mouth.
The door swung open, and Gloria stood there, cheeks flaming, turning around. “Oh! I—I’m sorry, Miss Montclair, Mr. Castillo, I just—needed—oh heavens—”
“It’s fine,” you managed between giggles, tugging Harry’s hands from your hair, keeping one in your grasp. “And Gloria?”
“Yes, Miss Montclair?” she squeaked, spinning towards you, her cheeks still crimson.
“Don’t tell my parents you saw us, please.”
Despite her blush, Gloria smiled wide. “Of course, Miss Montclair. Everyone’s gone back outside now.”
You winked at her, then dragged Harry across the kitchen and toward the stairs. He was right behind you, hands slipping over your waist, spinning you to the banister halfway up and stealing another kiss.
“Harry, we need to get to the room before someone sees,” you whispered, breathless as his mouth trailed hot, open kisses along your neck.
“Oh, for once you don’t want an audience?” he teased, lips brushing your pulse.
You giggled, shoving lightly at his chest. “Shut up.”
He caught your hand, grinning, and pulled you up the last steps. In the next breath, you were hauled up off your feet, his arms sliding around your thighs with a grunt. You squealed, clutching his shoulders, laughing into another kiss as he carried you toward the bedroom. His smile pressed against your mouth, his low moan curling into you as your fingers buried in his hair, tugging hard at the thick curls at his nape.
Carrying you across the threshold, the door clicked shut behind him, before he lowered you to your feet at the end of the bed. You landed softly in front of the bed frame, your heart still running wild, lips tingling from his kisses.
For a moment, he didn’t touch you. He just...looked. His curls were a bit disheveled, brushing over his brow, his chest rising and falling beneath that immaculate white suit. His eyes drank you in like he was memorizing every inch.
Then, with a quiet exhale, his hand lifted. He didn’t grab or rush, only brushed his knuckles along the fabric at your waist before finding the first knot that held your shirt together. His gaze flicked to your face, searching, waiting for any sign you wanted him to stop.
You didn’t.
Slowly, carefully, he tugged the knot loose. The fabric loosened, the tie dangling free, and he paused like unwrapping a gift he’d waited his whole life for. Then his hand found the second tie, pulling just as gently until the shirt came open and you slipped off your shoulders, sliding it down your arms in a soft whisper.
Harry’s breath caught. His deep molasses eyes moved over you, drinking in the sight of your bare chest before climbing back to your face. His lips parted as if he might speak, but no words came—just a deep, steadying sigh.
When he did find his voice, it was hushed, almost broken with how much he meant it. “Jesus,” he whispered, “You’re so fucking pretty.”
You smiled as his hand rose to trace lightly along your ribs, thumb brushing the swell of your breast, making you shiver. He was looking at you in a way that had you trembling for an entirely other reason, a look you’d seen before but didn’t know what it meant. But now, seeing him like this, you knew. He was looking at you like you were the only thing in the world worth looking at.
You slid his jacket from his shoulders, fingers going to his shirt buttons, but he caught your wrists gently, not to stop you, only to still you. “Why don’t you get on the bed for me?” he murmured, low and steady.
A sly smile curved your lips, and you saw the answering twitch of amusement in his brow. You sat down, crawling slowly and sinking back against the pillows at the top of the bed. You slid your linen pants down inch by inch, watching how his gaze followed every movement, the fabric pooling at your ankles before you kicked it aside, legs parting to reveal the lace clinging to you. Your fingers dragged up the inside of your thighs, and Harry stilled completely, shirt half undone, just watching.
“Gonna join me or just stare, daddy?” you teased, smiling.
He nearly choked on his shirt collar, “What was that?”
You giggled, winking. “Just wanted to see how you’d react.”
His laugh was low, rough in his chest as his shirt hit the floor. He tsk’d, “Such a filthy mouth on you, gonna need to fix that.”
The late sun poured through the gauzy curtains, lighting his skin in gold. Strong but soft, thick muscle covered by a belly that came with age. With or without clothes, it was clear Harry took care of himself, but the way his chest was dusted with dark hair that trailed down his stomach, disappearing beneath his slacks… you had to shut your mouth before any drool pooled out.
You sighed, trying to get yourself to settle, letting your head fall back against the pillows. Harry’s eyes followed your hands as you let them drag to your chest, cupping your breast, a gentle roll of your nipple before they pressed down your tummy, down beneath the waistband of your laced panties.
“Really gonna make me wait?” you pouted.
Harry pushed down his white slacks, his briefs tented beneath, “Never,” he whispered, beginning to climb up the bed to you.
He was so warm as his body eclipsed yours, finding home in the cradle of your hips. You whimpered, the thick swelling of his cock right up against where you wanted him most. Your hips rocked against him in need.
His hand brushed your hair back tenderly. “I’m sorry it took us so long to get here, sweet girl.”
You nodded, pouting again, your hands finding his thick banded arms, sliding up until you wrapped them behind his neck, pulling his thick hair, “You’ve been so mean,”
The words tugged at a memory—the car, when you’d said it before. Things had been jagged then, the air thick with silence and sharp edges. You’d been hurt, angry, and he’d been closed off in the way only he could be. But still, his hands had found you, he’d kissed you again, and even in the middle of all that hardness he had made you unravel. It wasn’t just lust you remembered—it was how desperately you had wanted him even when you knew you shouldn’t. Thinking of it now, your chest ached and your skin flushed all at once, that moment still alive inside you, proof of how long this pull between you had been waiting to break open.
“Didn’t mean to be.” His mouth traced along your jaw, your chin, brushing your lips, kissing your nose. “Wanted this for so long. Wanted you for so long. I should’ve told you.”
“Yes, you should’ve,” you bit his thick bottom lip when he kissed back down to your mouth.
He groaned, low and rough, answering by sucking your top lip into his mouth, holding it there until your breath stuttered. His wide hands slid higher, cupping your breasts fully, thumbs teasing over the sensitive peaks until a sharp gasp escaped you.
“You have no idea what you’ve done to me,” he said, as he released your lips with a pop, “Messed my head up. Got me feeling things I never—” He broke off, shaking his head, kissing you harder, deeper. His tongue pushed past the slant of your lips, molding to yours, key in lock, puzzle pieces, sealing together. You moaned, pulling on his hair as he pinched your nipples, his broad hands everywhere.
And then he released your lips to continue to map your skin, your breath heaving beneath his assault of kisses, giving you so much and yet never enough. You mewled, fingernails digging in his scalp, his nose nudged between the valley of your breasts, until his lips closed around your nipple, suckling it into his mouth, teeth coming down and biting, making you moan out loudly.
“Love the little noises you make too,” he said, “let me hear you, pretty girl,”
“Harryyyy…” you mewled, back arching, “you’re killing me,”
He removed his mouth, pouting back in mock sympathy, “What do you need, hmm? Tell me,”
“You,” you begged, voice cracking. “Anything, please. Please, please, please.”
“Okay, baby.” His laugh was low, fond, as he shifted down the bed, folding your thighs over his shoulders. He kissed your hip, the curve of your thigh, then the softer skin inside. “Haven’t stopped thinking about this pussy since the last time,” he murmured, pressing his mouth to the lace covering you. His eyes lifted, brown and blazing. “Tasted so sweet, took my fingers so good. Think she’s ready for more?”
“Yes, yes, yes,” you chanted.
His smile was sinful as his fingers hooked the waistband of your lace underthings. He tugged them down, letting your legs close around for a heartbeat before you kicked them off, and then he spread you open again, hunger written in his face.
Harry leaned in, no longer teasing or hesitating, and dragged the flat of his tongue through your folds, slowly, savoring the taste of you. The sound he made was nearly a growl, a deep rumble of satisfaction that sent shivers through your spine. His hands pinned your thighs apart, unyielding, as if nothing in the world would pull him from between your legs.
“God, baby…” he murmured against you, his breath warm, mustache brushing your sensitive skin, “Fuck, you taste so sweet, just like I remember,”
You whimpered, head tipping back into the pillows, your fingers tangling tight in his curls. He licked deeper, circling you, teasing before finally closing his mouth around your clit and sucking hard, hungry. Your body jolted, a strangled moan slipping out as your hips rocked against his mouth.
“Ah ah ah!,” you gasped, thighs trembling against his shoulders.
His eyes flicked up, locking with yours, dark and molten. He pushed a thick finger into you, slow, letting you feel every inch. The stretch made you gasp, your walls clenching greedily around him. “That’s it,” he rasped, curling it just right, “fuck—you’re so tight. Gotta get her ready for me, don’t I?”
Another finger followed, filling you, stretching you more. He pumped them in and out, steady and firm, his mouth never leaving your clit, his tongue laving over you in long, hot strokes. Your body clenched and fluttered, pulling him in deeper, welcoming him, needing him.
“Jesus Christ,” he groaned against you, the vibration making your toes curl. “The way you clench around me—your sweet pussy knows me, doesn’t it? Remembers my fingers, huh?”
You cried out, watching him as he looked up at you, his lips and mustache glistening as he growled up at you, “C’mon, right there, yeah that’s it,” he groaned, “that, right there, that’s mine now, isn’t it? Say it. Come on my fingers again and say it.”
“It’s yours, Harry, oh fuckfuckfuckfuck—it’s all yours—” your hands twisted in his curls, dragging his face closer, your hips rolling down to meet the thick press of his fingers. His mouth closed over your clit again, tongue flicking mercilessly, the sound of it obscene, wet, desperate.
You shook, thighs tightening and trembling as your back bowed, eyes rolling, that familiar crest approaching quickly, galaxies bursting behind your eyes. Your vision went white, sparks bursting behind your eyes, your body seized around his fingers. The sob ripped out of you as you clamped down, coming so hard you couldn’t even hold the sounds back.
He didn’t stop, not right away, but he kept you riding the wave, dragging it out until you were gasping, until the aftershocks made you kick against the sheets. Only then did he slow, easing his fingers free with a slick pull, kissing your clit once more before lifting his head.
His mouth was swollen, his chin shining with you, his eyes hot and tender all at once. He licked his fingers clean, groaning low in his chest, and shook his head with a small smile.
Harry kissed his way back up your body, lingering at your stomach, your ribs, the valley between your breasts. Each press of his mouth was unhurried, reverent, even as it latched around one nipple then the other, his tongue hot and wet against your pebbled skin. His fingers trailed with him, sliding across your skin, spreading the wetness he’d pulled from you.
When his lips finally reached yours, you tasted yourself on him, the kiss hot and unsteady, both of you greedy now. His hand cupped your jaw while the other fumbled at his briefs, pushing them down. The thick weight of him pressed against your hip, hot and slick.
“I need you,” you whispered, needy and trembling.
“I know, baby,” he muttered, kissing you harder, his voice rough with restraint. “Gonna take care of my sweet girl.”
Your thighs parted wider for him, and he guided himself to your entrance, the head of his cock slipping against you, catching in the mess of your arousal. The first push had you gasping, the stretch sharp and sweet, and he groaned low in his throat as he sank deeper.
“Jesus,” he hissed, his forehead pressing to your temple. “So god damn—taking me so perfect—”
The pressure built until he was fully seated, his hips flush to yours. As he bottomed out, he sucked in air through his teeth, baring them down at you.
“Ohhhhh Harry,” you mewled, your eyes rolling, your hips squirming to seat him, bearing the stretch of him.
“Please honey, I need you to be quiet,” he said, chest heaving, eyes screwed shut like he was barely holding himself together, "just for a moment—"
“You’re so—oh—you’re sooo b—hmppph—” The rest of your words were cut off by his hand clamping over your mouth, fingers spreading wide, swallowing your cries with ease. Your own digits found his wrist, clinging, moaning against his palm.
“Shut up, shut up,” he groaned, the sound fraying. “I’m sorry, I’m sorry, baby, can you be quiet for me? Jesus. S’just…this is not gonna last long if you keep—god, fuck, you just feel so fucking good.”
His voice broke on the last word, his breath catching. He blinked down at you, then lifted himself to look lower, his gaze fixed where your bodies joined.
You followed it, your own eyes going wide at the sight of him—so thick, it was nearly obscene that it all fit—pulling back a few inches, both of you moaning when you saw the thick length of him slick and creamy. He was covered your arousal and come, glistening all the way up to the dark tuft of hair above.
He thrust back into you slowly, the wet squelch depraved, the stretch so deep and heavy you thought you might split apart. Your eyes rolled, a broken moan tearing free from your chest as your body clenched down around him.
“That’s it, angel,” he murmured, voice hoarse with awe as he leaned down into you, his arms circling your body to keep you up against his chest. “Let me in. God, you’re perfect. You’re so perfect.”
Each word made your chest tighten, your eyes burn. You tilted your face into his, catching his mouth in a kiss that was more teeth and gasps than grace. Tongues pushing together, your own whimpers were eaten by his groans.
He drew back only to breathe, his nose brushing yours. “My girl,” he whispered, thrusting deeper, his pace quickening just a little. “You’re mine, sweetheart. Such a good girl for me. Always so good.”
Your walls clenched around him, your head falling back, and he followed your throat with his mouth, kissing down the line of it, nipping gently at your skin. He only lifted enough to slide one hand between you, finding your clit, his touch soft at first, then firmer as he felt you shudder.
Your hands wrapped around his shoulders, clutching, pushing, the feeling too intense, “S’too much, too much, Harry, oh oh oh—”
“That’s it, princess,” he said, only the shapes of words had his lips brushing yours. “It’s okay, feels good, doesn’t it? Give it to me. Wanna feel you come again, want to feel it on me—let me have it, baby. Let me take care of you.”
The rhythm of his hips grew heavier, his body pressing you into the mattress, his weight solid, grounding. The sound of your bodies together was wet and desperate, your moans mixing with his low groans as he kept praising you, every word sinking into your chest as much as the pleasure did.
His fingers circled your clit with a steady pressure that had your breath stuttering, your whole body tightening beneath him. Every thrust sent him deeper, his hips grinding against yours in a rhythm that made you ache, made you shiver.
“Sweet girl,” he whispered, his voice raw. “You feel so good, I don’t ever wanna stop. You’re everything, you hear me? Everything.”
Your thighs trembled, the heat rising, and you clung to him like he was the only thing holding you together. “Harry—” you gasped, your voice breaking, “I can’t—”
“Yes, you can,” he urged, forehead pressing to your temple, “You can, angel. Let go for me. Be my good girl and let go.”
The way he said it broke something open in you. Your body clenched down on him, sharp and blinding, and the world spun out of control as the orgasm ripped through you. You cried out, sobbing his name, and he groaned, guttural, his thrusts faltering as your walls clamped tight around him.
“Jesus, baby—fuck—” His face twisted, his hand coming up to grip your jaw as he buried himself deep, holding there as he came with you. His breath shuddered against your neck, hot and uneven, his body shaking as he spilled into you.
For a long moment, the world was nothing but the two of you clinging together, gasping, trembling, your hearts racing against each other’s sweaty chests.
He kissed your cheek, the corner of your mouth softly, reverently, his lips brushing your tear damp skin. Then he eased out of you, slow and careful, and you felt the warm spill of him follow, the evidence of it slipping between your thighs. He settled beside you with a heavy sigh, his arms reaching for you instinctively.
You rolled with him, curling across his chest, hands tucked under your chin as you looked up at him. He was smiling, soft and lazy, his eyes half-lidded but still bright as he brought you closer, pressing you tight to him.
You tilted your face and pressed a kiss to the rough thicket of hair along his chest. “Tell me a secret,” you whispered.
“A secret?” he chuckled, low and hoarse.
You nodded.
He blew out a long breath, his eyes flicking up to the ceiling like he was searching for something. “If I tell you my darkest one, you’ve got to promise not to tell.”
“Never ever,” you said quickly. “Scout’s honor.”
That earned you a crooked smile. “Highly doubt you ever did Girl Scouts.”
“It’s a turn of phrase, Harry,” you teased, nudging him. “C’mon now.”
He sighed again, fingers drifting lazily over your shoulder, trailing patterns on your skin. His voice was quiet, stripped bare, “Alright. A real secret, then.”
You tilted your chin into his chest, curious, waiting.
His eyes flicked down to you, soft but weighted. “I lied that night, when we were at my apartment. When I told you I didn’t know how to love.”
Your stomach flipped, but you waited.
“Maybe didn’t lie, but…I…I was already starting to feel it, something for you.” he admitted, his voice rough, uneven. “And I was so fucking scared.” his fingers were tracing your skin the entire time he spoke, “I’ve never been good at this—you know that by now. Love has always made me feel like a child. Foolish. I’d watch people fall into it so easily, and I just…couldn’t. As a kid I felt everything so strongly, and as I got older… I don’t know.”
You swallowed hard, remembering that night on his couch, the way he had looked so far away when he said those words, the defeat that had clung to him.
“I believed what I told you then,” he continued, his thumb brushing gently across your neck. “That I was incapable of it. That I was wired wrong. But the truth is, I was already falling, and it terrified me. Because for the first time it didn’t feel heavy, or complicated, or transactional.”
His mouth twitched like he was searching for the right words, eyes flicking away before landing back on yours. “It still makes me feel like a kid, but not the way it used to. Not dumb. Not...broken. With you, it’s different. With you, I feel… excited. Giddy, even. Like I get to start over. Like I finally understand what everyone else has been talking about all this time.”
Your chest ached, the sting of tears threatening again. You pressed closer to him, turning on your side so you could be as close as possible, nudging your head into the crook of his neck.
“Harry…” you whispered.
He gave the smallest, tenderest smile, turning to kiss your nose. “That’s my secret. That you make me feel like I’ve never missed a thing. Like I didn’t waste all those years after all, because they led me here. To this, to you.”
For a moment you couldn’t speak, your throat too tight. You hid your damp eyes against his neck as his hand smoothed over your back, steady and sure.
“Let me apologize again,” he murmured after a long beat, shifting so he could see your face, leaning over you with that earnestness in his eyes. Your head hit the pillows as you sniffled.
A small, wet laugh slipped out of you. “You already said sorry.”
“I want to say it again,” he insisted, voice low but firm. “I’ll say it every damn day until you believe me. Until you forgive me.”
Your heart throbbed painfully at the conviction in his tone. You shook your head and reached for him, pulling him down against you, your arms winding tight around his shoulders. “I do forgive you,” you whispered, your lips brushing his as you spoke.
His exhale shuddered against your mouth, and then he was kissing you again—slow, gentle, as if forgiveness was something he needed to taste to believe.
“What…what changed today?” you asked when he moved to kiss the corner of your mouth, your cheek.
He paused, eyes flicking over your face before dropping to the space between you. “It wasn’t today,” he said, his voice rough. “Truth is, I’ve been carrying it around for weeks now. Wanting to tell you, to try. I just…I didn’t know how. It’s my fault it’s dragged on this long, my fault you’ve been hurting. I hate it.” He pressed another kiss to your nose, tender, apologetic, it was like he was making up for all your lost time, the way he made sure to press his lips to every inch of you. “The difference tonight was seeing you run after Camilla. Watching you put yourself out there for her, knowing what it might cost you. You didn’t even think about yourself, you just…you just did it. And it hit me—I couldn’t keep holding it back. Not anymore.”
His words lingered, heavy and sweet, and you tucked yourself closer, pressing your lips to the hollow of his throat just as the faint buzz of your phone lit up the nightstand. A second later, Harry’s chirped too.
You groaned, flopping back again, rolling your eyes, “Here we go. Cue Gossip Girl.”
He reached across you, silencing his phone without even looking, and when he settled back, his arm draped over your waist. “Let her post. Let the whole damn city talk if they want. We’ll face it together like always.”
You turned your head to look at him, his brown eyes soft but steady.
“Do you want to see each other more seriously?” he asked suddenly, his voice quieter than before, almost shy, as if he wasn’t Harry Castillo but some boy testing the waters.
Your mouth curved into a small smile, the first laugh since tears had threatened again. “More seriously than you confessing your love for me, Harry Castillo?” you teased, brushing your nose against his. He huffed a laugh, shaking his head before kissing you again, deeper this time. You kissed him back harder, your lips still trembling with a smile as you climbed on top of him, knees bracketing his waist.
The phones buzzed again on the nightstand, but neither of you reached for them.
Notes:
a lot of readers on tumblr were wanting me to give harry a daddy kink so I gave you ONE daddy in here hahahahaha hope you enjoyed!!
Chapter 13: You Know You Love Me
Summary:
Leaving the house proves harder than it seems when Harry can’t keep his eyes off you.
Notes:
(See the end of the chapter for notes.)
Chapter Text
Harry, 1.5 years later
Harry gave one last flourish to the paper in his hands before setting it down on the coffee table. Bold type and glossy photos of his half-brother’s engagement sprawled across the front page, but he couldn’t bring himself to linger on it. All the noise of that world had grown tiresome, headlines that used to matter now paling against the quiet in his own home.
The quiet…and you.
From where he sat, he had a perfect view through the doorway of the main bathroom. You were bent toward the mirror, lips pursed as you fixed your gloss, tapping gently on your plush lips. The motion seemed so practiced he wondered if you even knew you were doing it. The dress you wore was one of those pieces designed to torment men like him—sheer chiffon that shifted every move you made. It bared more than it covered, high at the neck and scandalous everywhere else, the hem skimming the tops of your thighs. He thought you looked like every temptation he’d ever tried and failed to resist, like sin itself.
You’d worn things like this before, but back then you had worn them for the world. Now you wore them in his apartment, with your coat on the back of his chair, your perfume on his sheets, your laugh spilling through the halls.
He should have been used to it by now. Used to you leaving your trail everywhere, makeup scattered across his sink, your heels lined up beside his shoes by the door. But at forty-six, he still found himself staggered by the sight of you, twenty years younger and entirely unbothered by the hold you had on him. The truth of it hit him harder each time, as if it was sheer luck that he ended up here, with you. That he didn’t really deserve all this, this…peace, this happiness. Yet here you were, swaying slightly to the music you’d put on, catching his stare in the mirror like you’d known it was there all along.
His mind flicked back, uninvited, to all the times he’d tried to make love work. When he was seven, red-faced and clumsy, trying to win over Penelope Evans in his second grade class. Lucy, later, who he’d liked but never truly loved, but he’d tried to make it fit anyway, like forcing the wrong piece into a puzzle until the cardboard bent. The crushes in between weren’t much better—fleeting, shallow things that were quick to flare up and quicker to burn out. He had always been bad at that part.
But sitting here, watching you now, he knew every wrong start had led him to this. And he’d do it all again if it meant finding you that night at the hotel bar, when you had been coming apart at the seams, the papers ripping into you, your picture plastered everywhere. Anyone else would’ve said you looked ruined. But to him, you’d never seemed more alive. Sad, yes, broken even, but still burning underneath it, as if fighting to stay yourself while the world tried to strip you bare. He’d always thought you were pretty, sure—anyone could see that—but he hadn’t really seen you until then. The way you carried yourself, the way you’d surprised him by being kind in a world where kindness had gone scarce. Looking back, he knew that that was what made him want to strike the deal with you.
And now, contract forgotten and shredded, his eyes found yours in the mirror, your mouth tilted in that devilish little smile that always got to him. He rose before he knew he’d made the decision, the couch sighing beneath him as he pushed up and crossed the floor. His reflection appeared behind yours in the mirror as his hands slid easily around your waist. You fit against him like you’d been made for it, perfume lifting from your skin—Roja Haute, the one he’d given you, roses and jasmine warmed into something richer by your body’s heat. He buried his face against the curve of your neck, kissed the skin there because he couldn’t not.
“Harry, we’ll be late,” you said softly, amusement in the words even as your head tipped, giving him more.
“Let ‘em start without us,” he muttered, voice rough against your ear. His hands weren’t behaving, sliding up your body, brushing the sheer fabric, greedy for the warmth beneath.
“And miss my best friend’s engagement party?” you teased, though you turned in his arms anyway, hooking your fingers at the back of his neck.
He kissed you before you could say more, hard enough to smudge the gloss you’d been so careful with. Your lips parted, murmuring against his, “You’re going to ruin my makeup.”
“There’s a lot I’d like to ruin here,” he said, low, hand slipping into your hair, tightening just enough to tilt your head back.
You hummed, eyes fluttering shut, and that sound alone had him half gone. “Okay…” you whispered at last, lips brushing his around the words, “I wouldn’t be opposed to being fashionably late.”
Your laugh was still in his mouth when he slowed the kiss, softer now, taking but still gentle lingering. You leaned into him, warm, easy, gloss gone and not caring.
There was a time you would’ve been dragging him out already, eager for the party, for the eyes, for the proof that you were wanted. He remembered those long days and longer nights, remembered how you used to glow beneath the lights, soaking up every flash. But here, with your makeup scattered across his sink and your clothes shoved into his drawers, you looked brighter than you ever had out there.
He kissed you harder, backing you against the vanity until he lifted you onto the counter, your legs opening around his hips as his hands framed your face. His tongue pushed into your mouth, your moan breaking against him, and it sent his pulse into a reckless sprint.
“Let’s get married,” you breathed against him.
He stilled for half a second, heart skipping in its gallop—then huffed a laugh. “Should we announce it at the party tonight?”
Your eyes went wide, like maybe you’d expected him to shut you down, and then you giggled as his lips dragged down your neck, his fingers pulling at the neck of your collar to kiss your clavicle.
“Blair would kill me,” you murmured, head lolling as you welcomed his touch, but still a teasing lilt to your raspy voice. “We can wait ‘til tomorrow to tell her.”
Harry dropped lower, kissing down the line of your covered chest until he was sinking to his knees on the tile. He hiked one thigh over his shoulder, mouthing at the soft skin there. “And what kind of ring would you like, sweetheart?”
You brought your finger to your lips, teeth catching playfully as you looked down at him, wicked and sweet all at once. He began pushing your dress up higher, higher, a slow torment for the both of you.
“If I said I want an oval cut, ten carats, diamond band?” you teased, your voice pitching as his mouth pressed to your knee. “Or maybe an emerald. I’ve always liked—oh—”
Your breath hitched as his lips brushed the inside of your thigh, the heat of you filling his head, the scent of you dizzying him. He could’ve died happy there, kneeling at your feet.
“—I’ve always liked green,” you finished in a sigh.
“Done,” he muttered against your skin. “Anything you want.”
Your laugh turned into a shiver. “Just like that? You’d marry me?”
Harry’s mouth curved into a grin as he kissed higher, voice rough and low. “Sweetheart, I’d marry you right here on this floor if you asked.”
You whimpered when his lips brushed the crux of your thigh, cotton underwear already sticky and damp for him. His brain felt scrambled, drunk on the smell and heat of you. He rested his head against your thigh, kissed the rise of your mound, your dress rucked high around your hips.
“How about this one for now?” he asked, tapping your leg with the hand that always wore the gold band with its deep green emerald.
When he looked up, you were smiling through your breathlessness. He grinned back, lifted his head, nipped lightly at your skin, then tugged the ring free. You held out your left hand, and he slid it on.
It was too big, slipping sideways immediately, and you both laughed.
“I’ll get you one that fits,” he chuckled, lowering himself back between your thighs, one finger hooking the cotton aside to bare you to him.
Your fingers slipped into his curls, tightening just enough to hold him there, to make him lift his head and meet your eyes. Not rough or commanding, just a quiet insistence that he look at you. He didn’t care that you’d muss his hair, didn’t care about the gel he’d have to fix later. He was putty under your touch, waiting, watching, his breath catching as you kept him close.
“I don’t need anything else,” you said softly, “Just you.”
For a moment he only stared, chest rising hard, eyes searching yours, memorizing, cataloging how stunning you looked right now, bare to him, him bare to you.
“You’ve got me.” he croaked, “Always,”
You let go of his hair, delicate fingers petting down the side of his face as you lifted your thigh higher, resting your foot on the bathroom sink, spreading yourself open to him. His hands slid up to steady your hips, mouth lowering, breath hot against your skin. The perfume in the air mixed with the sharper scent of you, the room humming with nothing but your breaths, your pulse.
And there was nothing else that mattered. Not Gossip Girl. Not the tabloids. No audience, no eyes, no headlines. Just the two of you, hidden away, finally untouchable.
Notes:
Thank you to everyone who has loved and supported this fic from the very start! To my friends who looked things over for me, to those who talked me down when I was anxious, and to all of YOU for reading, commenting, and reblogging, I’m endlessly grateful. Truly, I couldn’t have kept writing without your encouragement.
Thank you for loving this fic as much as I have, for riding along on the wild Gossip Girl rollercoaster, and for letting me share this crazy idea with you. I hope to write these two some more in maybe some baby one shots. Okay, anyway, I LOVE YOU AND THANK YOU AGAIN!!!
xoxo, may
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