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?”