CEO Proposes A Fake Engagement Deal, Never Imagining He’d Truly Want The Woman By His Side

The Billionaire’s Proposal and the Public Facade

“Naomi, are you seriously turning down a half-million dollar deal to fake engage a billionaire CEO?”

Her best friend’s voice was shrill over the noise of the food truck crowd. Naomi Maddox blinked, still stunned by what had just come out of the man’s mouth.

Two minutes ago, she was standing on the rooftop of Valkcon Enterprises. The wind was catching her curls as she stared at Gregory Vale.

Yes, that Gregory Vale. He is a billionaire tech CEO infamous for never dating. He was currently offering her $500,000 to pretend to be his fiancée.

“Say something,” he said. His voice was cool and unreadable as he adjusted the cuffs of his tailored navy suit.

“I… I organize charity galas and handle donor lists. I’m not a con artist,” Naomi finally managed, her heart slamming in her chest.

“You’d be doing me a favor and getting paid for it,” Gregory said. His eyes locked on hers, unreadable green-gray and sharp as glass.

“My board is threatening to block the acquisition unless I settle down. They want stability—a family man. You’d be helping me close this deal.”

Naomi folded her arms. “Why me?”

“You’re not after me for my money. You didn’t even know who I was until last week.”

That part was true. She had bumped into him, literally, at a charity event she was working. He had spilled champagne on her clipboard. She had called him rude. He had been amused. Somehow, he had remembered her.

“And now this.” Gregory stepped closer, his voice dropping. “I need someone who can pull this off. You’re smart, you’re poised. You don’t stare at me like I’m a trophy. You’d be perfect.”

Naomi’s stomach flipped. “And what happens when your board approves the deal?”

“We break the engagement quietly. You walk away with the money and a glowing letter of recommendation from me. You can start your own nonprofit or fund ten.”

She looked down at her worn flats, then back at the man. He was offering her a life-changing sum of money with the ease of ordering lunch. She wasn’t stupid; this was insane.

But $500,000 could pay off her student debt and cover her mom’s medical bills. It could finally give her the freedom to start her dream education program for underprivileged girls.

Her voice came out small. “And we’d only be pretending?”

Gregory’s mouth twitched. “Strictly business.”

Naomi took a long breath. “Then fine. Let’s pretend.”

He held out his hand to shake. She hesitated, then took it. His grip was warm and strong. For a second too long, she stared at him. There was a flicker in his eyes, too, something unreadable.

“Let’s get engaged,” Gregory said calmly.

The next morning, Naomi found herself sitting in the back of a black Rolls-Royce. She was wearing a designer dress that had been delivered to her apartment minutes after sunrise.

Gregory slid into the seat beside her. He looked like he belonged on the cover of a finance magazine. His dark blonde hair was perfectly tousled thanks to some expensive stylist. He wore a charcoal suit that probably cost more than her rent for the year.

She cleared her throat. “You didn’t mention a photo shoot.”

“You’re my fiancée now,” his voice was calm, like he was talking about the weather. “The press needs to believe it. We’ll be seen around the city. We will do a few interviews and some charity appearances.”

Naomi groaned. “I hate being in front of a camera.”

Gregory glanced at her. “Then just focus on me.”

It sounded like a throwaway line. However, something about the way he said it made her heart skip.

By the end of the day, Naomi had been photographed with Gregory. They walked hand in hand through Central Park. They sipped espresso on the terrace of a five-star hotel and laughed.

She wasn’t actually laughing. She choked on a macaron outside of a jewelry store. To her horror, that turned out to be a real stop.

“Wait, what are we doing here?” she asked as Gregory held open the door to the gleaming boutique.

“Getting you a ring.”

Naomi froze. “I thought this was fake.”

“It is, but the ring can’t be.” He gestured toward the cases lined with diamonds. “Pick one.”

She blinked. “Gregory, I can’t wear a ring that costs more than my apartment.”

He walked over to the counter and pointed to a cushion-cut diamond set in platinum. “This one.”

The saleswoman’s eyes lit up. “Excellent choice, Mr. Vale. Four carats, flawless clarity.”

Naomi stared at the ring, then at Gregory. “You already picked it.”

He didn’t answer. He just slid the ring onto her finger. It fit perfectly.

The next week was a whirlwind. Naomi accompanied him to a black-tie gala. He introduced her as the love of his life. She nearly choked on her champagne.

He flew her to Boston on his private jet for a charity dinner. While cameras flashed, he leaned in and whispered, “Smile like you’re in love with me.”

She did. For some reason, it wasn’t as hard as it should have been.

They spent hours together learning each other’s stories and practicing their origin tale. They laughed over takeout in his penthouse kitchen when a photo shoot ran late.

Strangely, Gregory wasn’t the cold billionaire she thought he’d be. He was intense, yes, and focused, but he listened when she talked. He remembered everything she said.

He noticed when she was tired. He ordered her favorite tea without asking.

One night, after a long board meeting, they sat on the terrace of his penthouse. They overlooked the city skyline. Naomi wrapped her arms around herself. “You ever get tired of pretending?”

Gregory didn’t look at her. “All the time.”

She turned to him. “Then why do it?”

He looked at her then, his voice softer than she’d ever heard. “Because sometimes pretending is the only way to get what you want.”

Naomi didn’t know what to say, so she looked away. But she felt it—the shift. Something was changing. A line was blurring, and she wasn’t sure if she wanted to stop it.

The next morning, the headline was everywhere: “Gregory Vale’s Fiancée: Who is Naomi Maddox?”

Her inbox exploded. Her phone rang non-stop. Her nonprofit clients were confused. Her mother was overjoyed.

And Gregory? He just handed her a coffee as she walked into his office, calm as ever.

“You okay?” he asked.

Naomi stared at him. “No, I’m not. This is getting out of control.”

He nodded. “I’ll handle it.”

“You can’t just fix everything with money.”

He looked at her. “Then I’m not trying to fix it. I’m trying to protect you.”