Billionaire Needed A Date For Wedding, Never Expected His Assistant’s Roommate Would Steal His Heart
A Business Proposal
The shattering of glass echoed through Nathan Young’s penthouse office as his Italian leather shoe connected with an empty crystal tumbler. He sent it careening across the polished marble floor. His frustration wasn’t aimed at the innocent glassware but at the text message glowing on his phone screen.
His date for his cousin’s wedding, scheduled for this weekend, had just canceled. In the cutthroat world of luxury real estate development, Nathan had conquered every challenge thrown his way. But finding a last-minute replacement for a high-profile family wedding was proving to be his Waterloo.
His insufferable relatives would probe into his personal life. “Perfect timing as always, Vanessa,” he muttered, running a hand through his dark hair as he paced beside floor-to-ceiling windows overlooking Manhattan. The skyline, dotted with buildings he owned, usually calmed him.
Today, it only reminded him of how much control he normally maintained in his life—control that was quickly slipping away. Nathan pressed the intercom button on his desk.
“Melissa, can you come in here, please?”
Moments later, his assistant appeared, tablet in hand, her expression expectant.
“Yes, Mr. Young?”
“Vanessa just canceled for the wedding,” he said bluntly. “I need a date. Someone presentable and intelligent who can handle my family without making a scene.”
Melissa’s eyes widened slightly. “For this weekend? The Connecticut wedding?”
“Yes, the very same four-day extravaganza my aunt has been planning for months. The one where I’ll be interrogated about my personal life by relatives I see once a decade.”
His voice had an edge to it he rarely used with his assistant. “Sorry, I’m not upset with you. This is just inconvenient.”
Melissa nodded, already tapping away on her tablet. “Let me check some options. The usual escort services?”
“No,” Nathan interrupted. “No escorts. My family would see through that immediately. I need someone real, someone who feels authentic.”
A thoughtful expression crossed Melissa’s face. “What about a friend? Someone who isn’t connected to your business circles?”
“All my friends are business associates. You know that.”
Nathan leaned against his desk, loosening his tie slightly. At thirty-five, he’d built Young Development into one of the most successful real estate empires in New York. However, his personal life had taken a distant second place to his ambition.
“Actually,” Melissa said hesitantly, “I might have a solution. My roommate just had a breakup and canceled her vacation plans. She’s taking time off work but has nothing to do now. She’s smart, presentable, and honestly could use the distraction.”
Nathan raised an eyebrow. “Your roommate? What does she do?”
“She’s a children’s book illustrator—freelance. Very talented.”
Melissa’s voice had gained confidence. “She’s nothing like the women you usually date, but that might be an advantage. She feels real because she is real.”
“An illustrator?”
Nathan couldn’t keep the skepticism from his voice. “Would she even be comfortable in that environment?”
“Clare is surprisingly adaptable. She grew up with money before her parents lost everything in the 2008 crash. She knows how to navigate those circles, even if she’s not part of them anymore.”
Nathan considered this as he walked back to the window. His reflection stared back at him: tailored suit and carefully styled hair, the image of success. What would it be like to bring someone completely outside his world to this wedding?
“Fine,” he finally said. “Set up a meeting for this evening. I need to make sure she’s suitable before committing.”
Melissa nodded briskly. “I’ll arrange it. Shall I have the car bring her here, or would you prefer a more neutral location?”
“The rooftop lounge at the Whitney. 7:00. And Melissa,” he paused, “make sure she understands what she’s getting into. Four days with my family isn’t a vacation.”
“I’ll brief her thoroughly,” Melissa promised, already texting as she left the office.
Nathan turned back to the skyline, wondering what he just agreed to. He had built his life on calculated risks, but this felt different. It was personal, unpredictable, and everything he typically avoided.
Clare Fuller stared at her phone in disbelief. “Mel, you can’t be serious. A billionaire needs a fake date to a wedding and you volunteered me? This isn’t a Hallmark movie.”
Melissa laughed, her voice tinny through the speaker. “It’s perfect timing. You were just complaining about spending your vacation alone in the apartment after Ryan canceled your trip.”
Clare flopped back onto her bed, surrounded by half-finished illustrations for her latest project. Watercolor brushes and paint tubes were scattered around her, a riot of color against the white comforter.
“There’s a difference between not being alone and pretending to date a billionaire at a fancy wedding,” Clare retorted. “I don’t even know this guy.”
“You know of him,” Melissa countered. “Nathan Young. He’s actually a decent boss—just intense and focused. He needs someone normal who won’t embarrass him in front of his family, but also won’t try to trap him into a real relationship.”
Clare snorted. “And that’s me? The perpetually single illustrator who spends most days talking to fictional characters and animals?”
“That’s exactly why it’s you. You’re genuine, Clare. And after what Ryan did, wouldn’t a weekend at a luxury estate in Connecticut be better than moping around our apartment?”
Clare sighed, touching the edge of a watercolor painting of a bear and a little girl having a tea party in the forest. Her deadline was coming up, but the work was nearly done.
Melissa had a point about the moping. The breakup with Ryan three weeks ago had left her wounded, especially when he’d immediately started dating the woman he’d assured Clare was just a colleague.
“What would I even wear to something like this?” she asked, a hint of interest creeping into her voice.
“He’ll take care of that. The man has connections to every high-end designer in New York.”
“That’s weirdly transactional,” Clare murmured.
“It’s practical. Look, just meet him tonight. If you hate him, say no. He’s meeting you at the Whitney at 7:00. Wear that navy dress with the silver earrings.”
Clare glanced at the clock. It was 5:30 p.m. “Mel, that’s in 90 minutes!”
“Better hurry then,” her roommate chirped before hanging up.
Clare stared at the ceiling for a long moment, considering what she was about to do. Meet a billionaire? Potentially agree to be his fake date for a four-day wedding? It was insane, and yet she found herself heading for the shower.
The rooftop lounge of the Whitney offered a panoramic view of New York City as the setting sun painted the skyline in shades of amber and gold. Nathan arrived fifteen minutes early, securing a corner table that afforded both privacy and a spectacular view.
He ordered a scotch, neat, and scanned the entrance with practiced casualness. At precisely 7:00, a woman stepped onto the rooftop, pausing to take in the view. Nathan recognized her immediately as Melissa’s roommate, though she looked nothing like he’d expected.
He’d imagined someone more artistic—bohemian, perhaps. Instead, Clare Fuller was polished but understated in a simple navy dress that complimented her auburn hair, which fell in loose waves past her shoulders as she approached.
Directed by the host, Nathan stood. Their eyes met, and he was struck by the directness of her gaze. It was curious and appraising, but without the calculation he was accustomed to seeing in women introduced to him.
“Mr. Young,” she said, extending her hand. “I’m Clare Fuller, Melissa’s roommate.”
Her handshake was firm, her smile cautious but genuine.
“Nathan, please,” he replied, gesturing to the seat across from him. “Thank you for coming on such short notice.”
“Well, it’s not every day I get summoned by a billionaire,” she said with a hint of humor in her voice. “Though I should warn you, I’m still not entirely convinced this isn’t an elaborate prank.”
A server appeared, and Clare ordered a glass of Sauvignon Blanc. Nathan watched her, reassessing. There was something refreshing about her lack of pretense.
“Not a prank, unfortunately,” he said once they were alone again. “Just a genuine predicament. Has Melissa explained the situation?”
Clare nodded, a hint of amusement playing at her lips. “You need a fake girlfriend for a family wedding because your real date canceled. It sounds like the plot of a romantic comedy.”
“I assure you my family is far less charming than any fictional counterpart,” Nathan replied dryly. “The wedding is my cousin’s—four days at my aunt and uncle’s estate in Connecticut, beginning this Friday. It will be intense.”
Clare took a sip of her wine, studying him over the rim of her glass. “Why me? Surely there are plenty of women in New York who would jump at the chance to be on the arm of Nathan Young for a weekend.”
The question was blunt, and Nathan appreciated that. “Precisely because of that. I don’t want someone with ulterior motives or who’s starstruck by wealth. My family is perceptive. They’d see through it immediately.”
“And you think they won’t see through us?” Clare challenged.
Nathan leaned forward slightly. “I think you’re intelligent enough to pull this off without overacting or trying too hard. We don’t need to convince them we’re madly in love, just that we’re dating and getting to know each other.”
Clare nodded slowly, considering his words. “What would this entail exactly, besides showing up and making small talk?”
“Attending the welcome dinner Friday night, various activities Saturday, the ceremony and reception Sunday, and a farewell brunch Monday before departing,” Nathan explained.
“We’d need a basic backstory of how we met—something plausible but not overly complicated. And you’d need appropriate attire, which I’ll arrange.”
“I have clothes,” Clare said automatically.
“Not for this,” Nathan replied, not unkindly. “This is old Connecticut money mixed with new tech wealth. The dress code is specific.”
Clare raised an eyebrow. “And in return for playing arm candy for four days?”
Nathan bristled slightly at the term. “You wouldn’t be arm candy. You’d be my date. As for compensation, I’m prepared to pay you $10,000 plus cover any expenses related to the weekend.”
Clare nearly choked on her wine. “$10,000 for a weekend?”
“Four days,” Nathan corrected. “And yes, your time is valuable, as is your discretion.”
Clare set down her glass, her expression suddenly serious. “I’m not an escort, Mr. Young.”
“I never suggested you were,” he replied, matching her tone. “This is a business arrangement between adults. No romantic or physical expectations whatsoever.”
Clare studied him for a long moment, and Nathan had the distinct feeling he was being evaluated in a way few people dared to assess him anymore.
“I have some conditions,” she finally said.
Nathan gestured for her to continue, intrigued.
“First, I’ll accept necessary clothing, but nothing extravagant or that feels like you’re dressing me up like a doll. Second, I won’t lie about who I am or what I do.”
“If your family asks about my work as an illustrator, I’m going to tell them. Third,” she hesitated, then continued with determination, “I won’t be controlled. If I’m uncomfortable with something, I’ll let you know privately and you’ll respect that.”
Nathan considered her terms. They were reasonable—more than reasonable, actually. Most people would have simply named a price.
“Agreed,” he said. “I have one condition of my own. We present a united front. Any disagreements remain private. My family can be challenging; they’ll exploit any perceived weakness.”
Clare nodded. “Fair enough. Then we have a deal.”
Nathan extended his hand across the table. Clare hesitated just a moment before taking it.
“We have a deal.”
Her hand was warm in his, the touch lingering perhaps a second longer than necessary. Nathan felt an unexpected flutter of anticipation, not for the wedding, but for the company he’d be keeping.
“So,” Clare said, breaking the momentary tension, “tell me what I need to know about the Young family dynasty.”
Nathan’s mouth curved into a half-smile. “How much time do you have?”
