CHAPTER THREE THE GAMBLER

Love has always been a gamble.

At least, that's how Sam saw it most of her life.

While some people dreamed of fairytale endings and soulmates found on dating apps, Sam preferred to keep her feet firmly on the ground (and her phone away from Tinder). Around her, it often felt like everyone was either frantically searching for "the one" or entangled in some exhausting talking stage that could rival a slow-burn romance novel.

Still, despite her jaded view of modern dating, Sam wasn't bitter. In fact, she was genuinely happy for her sisters who seemed to have found their perfect matches. Her older sister, Vinny Alcott, was already engaged to her long-time accountant fiancé, Danny Woodhouse. With wedding bells possibly chiming later this year, Vinny was deep into color palettes and invitation fonts. Then there was their half-sister, Sue Mikhasen, who had been in a solid, drama-free relationship with her college sweetheart, Adam Lyndon.

The only single ones left in the family? Sam and the youngest among their siblings, Ellie Mikhasen. But Ellie had a valid excuse: she was knee-deep in her Master's for Psychology and barely had time to eat a proper dinner, let alone go on dates. Sam, on the other hand...

Well.

"You always make so many excuses," Vinny would say, eyebrows arched, while flipping through wedding magazines.

Love is still elusive for her. No matter how many days passed or how many well-meaning friends hinted at matchmaking, it remained just out of reach like a mirage that shimmered, beckoned, then vanished when approached. She often wondered why humans crave companionship so desperately, as if it were the ultimate prize, the final piece of some puzzle everyone was secretly assembling.

Was it really worth it? Married couples never talked about the mess behind the scenes. Marriage, after all, wasn't just about love, it came with its own maze of complications: compromises, misunderstandings, silent expectations, and the quiet erosion of solitude. And then, of course, came children. Society praised it as the next great milestone, but to Sam, it sounded more like willingly handing over your sanity. The sleepless nights, the endless demands, the constant pressure to be everything at once—nurturing, patient, perfect.

Let alone the daily drudgery: scrubbing floors that would only get dirty again, cooking meals that would be devoured in minutes, and trying to maintain some semblance of self amidst it all. She couldn't help but think, why was this the gold standard? Why did no one admit how exhausting it looked from the outside?

But then, love has many forms for her.

Sam came from a large, complicated, but close-knit family.

Her mother, Sara Tajiri, had been married twice. The first marriage was to Sam and Vinny's father, Joseph Alcott. It didn't last. The reasons were layered, but it mostly came down to deep differences in values and how they saw the future. Joseph was structured and pragmatic, someone who believed in timetables, order, and quiet logic. Sara, on the other hand, was more intuitive, passionate, and emotionally expressive. Over time, their differences stopped complimenting each other and started building distance. The separation wasn't messy—just inevitable.

Still, Joseph remained in Sam's life. He later remarried a woman named Elaine Uyen. By all accounts, Elaine was everything people hoped for in a stepmother. Calm, nurturing, and immensely thoughtful, she brought a sense of warmth into Joseph's otherwise rigid world. And she could bake like it was a calling. Every visit to their home in Long Island meant homemade pastries, fresh bread cooling on the counter, and the quiet comfort of routine. Sam missed that house more than she let on; the quiet neighborhood, the hum of the kitchen, the evenings where everyone sat around and talked without checking their phones every few minutes.

Through that second marriage, Sam gained another sister, Faye Alcott-Enriquez. Faye was younger than Sam and Vinny but carried herself with grace and conviction. She had recently married Romeo Enriquez, a man whose quiet strength and easy kindness made him instantly likable. He treated Faye with a kind of respect that felt both steady and effortless. Like Vinny's fiancé, Danny, and Sue's longtime boyfriend, Adam, Romeo seemed to fall into that same rare category: a walking green flag.

Sam couldn't ignore the pattern.

Vinny had Danny. Sue had Adam. Faye had Romeo.

Each of her sisters had somehow found men who were stable, respectful, and deeply committed. There was no drama in their relationships, no uncertainty. Just a steady kind of love that held up in the long run.

Unfortunately for Sam, finding love is exhausting. She had gone on multiple dates over the years; some good, some awkward, and some that made her wonder if she was being pranked. After a while, the novelty wore off. The small talk, the ghosting, the vague "Let's hang out sometime" texts where it all felt like déjà vu on a loop.

Eventually, she just...stopped trying.

Now, her time and energy were mostly funneled into work, where things were at least more predictable. She can't help but admit that working with Harry Castillo has some perks. His love life was a rotating door of models and the occasional non-existent actress, and yet, Sam couldn't deny it—he made her routine life entertaining.

Between managing his calendar, coordinating meetings, and fending off his flirty texts (half-serious, half-satirical... probably), Sam found herself surprisingly not bored.

At least one thing is constant in her life; her job with Harry Castillo.

Also, the money that goes with it.

"For the love of God, Sam. Just try going. Just once," Mitchel Devlin said, folding her arms as she leaned back in the booth. Her auburn curls were pulled into a loose bun, and her sharp eyes, always observant, always just a little too knowing were fixed on Sam. They'd been friends since college, and Mitchel had long since earned the right to push a little harder when Sam started building emotional walls again.

The topic was an unwelcome guest: Sam's non-existent dating life. Or, as her friends preferred to frame it, her stubborn refusal to give anyone a chance. Tonight's nudge? An arranged date downtown. Set up by Rhiannon, of all people.

Sam sipped her cocktail with calculated disinterest, hoping the drink would shield her from further interrogation. "Arranged dates are archaic," she muttered. "Might as well ask me to write a freaking dowry."

Across the table, Rhiannon Haley let out an exasperated sigh. Rhiannon was the kind of woman who made chaos look curated—flawless even after back-to-back meetings, with an Instagram story always ready. Despite a crushing schedule as a retail Sales Manager, she somehow had a social calendar that would tire a college freshman. Sam had yet to figure out if Rhiannon was secretly powered by espresso or dark magic.

"Oh please," Rhiannon said, raising a perfectly groomed brow. "When was the last time you had sex?"

Sam choked slightly, caught off-guard. "That escalated quickly."

Mitchel snorted into her drink. "That's Rhiannon's version of foreplay. Direct and mildly terrifying."

Both women laugh while earning an eye-roll to Rhiannon.

"I'm not going to discuss my body count here," Sam replied, adjusting the sleeves of her cardigan, suddenly hyper aware of how buttoned-up she probably looked next to her two dazzlingly confident friends.

"You need to loosen up," Rhiannon pressed. "Also, I know your idea of flirting is correcting someone's grammar on a dating app."

"Proper use of 'they're' is sexy, thank you very much."

Mitchel leaned forward, her voice softening. "Sam, look. We love you. We're not saying you need to be with someone. But you deserve something good. A real connection. You've been carrying so much, for so long—you've forgotten how to let yourself want something that isn't safe or practical."

There it was. The weight under the teasing. Mitchel had always known how to hit the nerve gently, like pressing on a bruise just to remind you it's still there.

Sam didn't answer right away. She stared at her glass, then at her two friends — both so different, both somehow still managing to believe in her, in the possibility of more.

She sighed. "Fine. I'll go. But if this guy turns out to be a crypto buyer, I'm holding you both personally responsible."

"Fair," Rhiannon said, raising her glass.

"But if he's hot and reads Murakami? You're welcome," Mitchel added with a wink.

Sam sat perched on the edge of a plush armchair in the lobby of the Aman New York, the kind of hotel where everything whispered luxury. From the hushed jazz drifting through invisible speakers to the champagne-toned light fixtures casting a golden haze over polished marble floors.

Her phone screen was lit up again, tilted subtly so no one could see it. She was staring yet again at the picture Rhiannon had sent her of the date.

The man in the photo, Vincent Schneider, looked like someone cast for a Netflix legal drama: well-fitted charcoal suit, a jawline you could hang art from, and that careless kind of handsomeness only the French seemed to master. According to Rhiannon, he was 5'9", a lawyer, and in his late thirties. Clean, charming, and (allegedly) single. The kind of man Sam would normally side-eye with suspicion.

Still, she'd saved the picture.

Rhiannon had been smug the night before, swirling wine in her glass like a matchmaking villain. Sam had interrogated her, of course.

"Be honest," she'd said, squinting over her stemless cabernet. "Did you go out with him first and it didn't work out? Is this one of your classic 'recycle and reassign' setups?"

Rhiannon had laughed too hard, which wasn't not a confession. "Absolutely not. Maybe. Who cares? You'll thank me later."

Mitchel just let out a hearty laugh. Of course, social cues are not Sam's greatest feat so she still doubts the credibility of this date.

Now, in the lobby, Sam shook her head and smiled in spite of herself. The idea of this date still felt idiotic but it was actually happening. And the man was objectively attractive, a rare enough feat for Rhiannon's setups.

She was so deep in her daydreaming spiral that she didn't notice the glass doors of the conference room swinging open.

"Something bothering you?"

Sam jumped slightly in her seat, phone nearly slipping from her hand. She looked up to see Harry standing in front of her with that signature half-smile that always straddled the line between charming and arrogant.

Sam straightened instantly. "No. I'm fine." She shoved the phone into her blazer pocket like it had personally betrayed her.

Harry gave her a look. One eyebrow raised. He was still in his tailored navy suit from the board meeting, tie loosened just enough to look deliberate. The man could sell sand to a desert. Or, more accurately, negotiate a multimillion-dollar expansion deal while looking like he belonged on a yacht catalog cover.

"You sure?" he said as they started walking toward the exit. "You had that glazed-over look people get when they're deciding between running away or texting back."

"I was reviewing logistics," she lied smoothly.

"For the hotel expansion?"

"Sure." She did not need him to know about her predicament in dating.

As they stepped out into the cool midday breeze on Fifth Avenue, the rhythm of Manhattan life wrapped around them; taxis honking, tourists pointing, luxury storefronts gleaming.

"How was the meeting?" she asked, grateful to pivot. She glanced down at her sleek black leather planner, flipping to today's schedule.

"The board's chewing on it," Harry said, shoulders lifting in a lazy shrug. "They're intrigued by the idea, but no one in the family's ever tried infiltrating Asia. Expansion into the Pacific is... uncharted."

Sam nodded, scribbling a note. "Makes sense. Conservative old-money instinct."

Harry tilted his head. "That's a polite way to say they're scared shitless."

She smiled. "It's a legal record. I'm not allowed to quote you."

They paused at the valet station. Sam scanned the agenda. "You've got the charity auction tonight. 7 p.m., uptown."

Harry sighed heavily,  "Do I really have to go to that?"

"It's for pediatric cancer research," Sam said, deadpan. "You want to be the billionaire who said no to the kids?"

He squinted at her. "You're enjoying this."

"Not even a little," she said. She was absolutely enjoying it.

"Will there be shrimp skewers?"

"If you behave."

Harry smirked and loosened his tie another fraction. "Then I guess I'll show up. But only for the kids. And the shrimp."

Their banter was casual, but Sam felt the usual buzz beneath it; the careful balancing act of personal and professional. Harry is a different kind of boss. He didn't bark orders. He teased her sometimes. He noticed things. He asked questions he wasn't supposed to.

Still, he was her boss. And tonight, after wrangling him through a charity event, she'd be walking into this date with a French lawyer and the kind of nerves she hadn't felt since high school.

Harry stood in front of the tall mirror near his wardrobe, shoulders squared, brow furrowed as he tried for the fourth time to tame the bow tie around his neck. It was the only part of his tuxedo giving him trouble—everything else was pristine: sharp lapels, polished cufflinks, and shoes shined to a mirror finish. But the tie? The tie had declared war.

Behind him, he heard the familiar click of stilettos on hardwood.

His eyes lifted to the mirror.

And for a moment, he forgot the tie altogether.

Sam appeared from the guest room, a garment bag tossed over her arm, but what caught his attention was the sleeveless red dress hugging her frame. It wasn't flashy but in fact, Sam wasn't the flashy type, it was devastating in its simplicity. The kind of red that made a man forget his own name. Her lipstick matched it perfectly, and her dark stilettos clicked sharply against the hardwood floor as she crossed the room toward the bed.

Harry's mouth opened slightly. Then closed.

She walked past him like nothing was unusual, heading straight for the bed where she laid out his gold watch, pocket square, and a pair of cufflinks.

"Still losing to the bow tie?" she asked, tone dry, not even looking up.

"It's defective," he muttered. "Sabotage, maybe."

"Come here."

He turned toward her, obediently stepping closer. Sam reached up, her fingers working with calm precision. She undid the crooked knot, her touch light but sure, her brows furrowed just slightly in concentration.

"You know how to tie one of these?" he asked, half surprised.

"You think I've worked this long and haven't learned how to rescue a tuxedo?" she replied without missing a beat.

Her fingers moved quickly—looping, pulling, adjusting. Her face was close to his chest, her scent subtle and warm, and for a moment Harry forgot what they were even talking about.

He glanced down at her. His eyes wandered to the curve of her shoulder, the delicate gold earrings, the dress that looked as if it had been made with her in mind. She didn't notice. She was still focused, tugging one last loop into place before stepping back.

"There. You're now fit for public consumption."

"I was before," he said lightly, adjusting the sleeves of his jacket.

She rolled her eyes and picked up the gold watch from the bed, sliding it onto his wrist.

"What time do we need to be there?" he asked, checking the mirror again.

"We're leaving at five." She glanced at her phone. "Also, I might need to leave the auction by six."

"Who is the lucky guy?" he asked casually, though there was a subtle curve at the edge of his lips.

She hesitated but just enough to be noticeable.

Harry raised a brow, clearly amused. "Knew it."

"It's not like that," Sam said quickly, smoothing the lapel of his tux. "It's a setup. A friend's idea."

Harry leaned slightly against the side table, arms crossed. "Sounds suspicious already."

"Oh, it is. French lawyer. Late thirties. Sounds like he could either charm me or sell me a timeshare."

Harry chuckled. "At least you look like you're the one doing the interviewing."

She gave a small, self-deprecating smile. "That's the plan."

He offered his arm. She took it without hesitation.

As they walked toward the private elevator, the evening air waiting for them beyond, Harry glanced down at her one more time.

"You know, if it doesn't work out with the Frenchman..." he said casually.

"Don't finish that sentence, Castillo." She knew that it's harmless teasing. As always. She can hear his laughter as the elevator doors slid open.

"Fine. I'll just stand near the shrimp skewers and try not to faint from boredom."

"You'll survive until six." She stepped in beside him. "And after that, you're on your own."

The annual charity auction was the kind of event that existed in magazines—marble floors, a sweeping ballroom lit by a galaxy of crystal chandeliers, and the soft clinking of champagne glasses echoing beneath muted jazz. Wealth was woven into the walls, stitched into every detail from the monogrammed napkins to the gilded bidding paddles arranged like silent invitations.

Harry Castillo and Samorn Alcott arrived just on time. As always.

And as always, Harry didn't even have to speak before people noticed him.

Sam stepped slightly behind him as they entered, instinctively falling into the rhythm of her role. The room shifted the moment Harry walked in who has a subtle current of attention turning in his direction. A few of the women near the silent auction table smiled with too much familiarity. Several of them reached out to touch his arm or lean in too closely under the guise of saying hello.

Sam watched with a trained, neutral expression. She'd seen it all before.

Of course he was surrounded. He is Harry Castillo—a bachelor, a billionaire, and unapologetically charming. If there was a socialite in New York under forty, odds were Harry had dated or slept with. Sometimes both. Sam had no illusions about that. He never lied about what he wanted, and most people didn't care. Not when he looked like that and had that name.

She quietly stepped away toward the front seating area, needing a moment. Her heels clicked softly on the marble as she adjusted her clutch under one arm and scanned the auction catalogue, half pretending to read it, half trying to keep her nerves in check. She had a date later. A blind one. And the closer six o'clock got, the more foolish she felt.

"Excuse me," a smooth voice interrupted her thoughts.

She turned.

A man in his thirties stood before her, handsome in a sharp navy tuxedo and wearing a confident ease that suggested inherited money and boardroom experience. His smile was polite but deliberate.

"Andrew Peppard," he said, extending a hand. "I don't believe we've met."

Sam shook his hand firmly. "Sam Alcott."

"Pleasure. Are you with one of the firms, or just here for the wine and art?"

She smiled lightly. "Here for work."

Andrew studied her. "Let me guess, Castillo Group?"

Before she could answer, a voice came from her side. Controlled. Even. But not casual.

"That's right."

Harry.

He appeared beside her with his usual smooth composure, a drink in hand and a look in his eyes that told her he'd been watching.

"She's my assistant," he said simply, eyes locked on Andrew.

Something shifted between the two men. It was small, but Sam felt it instantly. A stillness. A quiet readjusting of posture—Andrew's smile thinned, and Harry's tone sharpened just slightly.

"Didn't realize you traveled with your assistant to these things, Harry."

"Sam manages my calendar, my press, and keeps the board from setting fire to half my schedule. I'd say she travels exactly where she needs to be."

Andrew gave a half-laugh, the kind that didn't quite reach his eyes. "Sounds like you've got yourself a good one."

Then he turned to Sam again, his smile softening. "If you ever get tired of babysitting billionaires, I know a few companies that would fight to hire you."

Before she could say anything, Harry's voice cut in again; still polite, but with steel underneath.

"Call first."

Andrew nodded, clearly understanding he was being dismissed. "Good seeing you, Harry." And to Sam, more lingering this time: "Until next time."

Sam watched him leave, tension easing just slightly as the air cleared.

"He seemed... intense," she said, watching Andrew disappear into a cluster of donors near the wine tasting booth.

"He's harmless," Harry replied, but his gaze stayed on Andrew a moment too long.

There was something else beneath his words. A protectiveness that didn't quite fit into the usual professionalism he wore like a suit. He was measured, but not cold. Calm, but not indifferent.

Sam checked her phone. 5:58. She swallowed the flutter of nerves in her throat.

"Just a reminder, I'll need to leave by six," she said, glancing up at him.

Harry didn't respond right away. His gaze returned to her, but softer now. Focused.

"Understood," he said. Then after a short pause, "Text me when you get home."

It was said simply, as though it were part of her job. But it landed heavier than that.

She gave him a nod, brushing it off. "Sure."

And then she turned away to find her seat, the red of her dress catching the light as she moved poised, and composed, but quietly unraveling inside.

She had bigger things to focus on tonight. A date. A maybe. A stranger waiting somewhere downtown.

She didn't look back at Harry.

But he watched her go, jaw tightening, the whiskey in his glass still untouched.

anj speaks

so obsessed with them!!!! manip made by me <3