Grayson stepped out of the sleek black car and onto the bustling streets of Manhattan. The warm, tropical breeze of Hawaii felt like a distant memory as the crisp March air of New York wrapped around him. He tugged at his coat, adjusting to the shift, both in temperature and in pace. Hawaii had been a brief escape, but now he was back in the thick of it—mergers, acquisitions, boardroom battles, and endless meetings.
The only silver lining? Olivia wasn't too far away.
He hadn't originally gone to Hawaii for a vacation. His friend Daniel had been trying to set him up with a woman named Liv, but fate had other plans. On his way there, he had run into Olivia—the woman who seemed to cross his path no matter where in the world he was. And after that unexpected, electrifying kiss at the airport, followed by their late-night banter that had left him grinning like an idiot, he couldn't get her out of his head.
Yes, Olivia lived in Chicago. But that was just a technicality when it came to negotiations. And with Olivia, there was definitely a deal to be made. She wasn't the type to make things easy for him—her betting game and razor-sharp wit ensured that. But rather than deterring him, it only intrigued him more.
Their last conversation replayed in his head. The teasing. The challenge. The way she never let him off easy.
Grayson: One kiss from you is not enough.
Olivia: Sounds like a personal problem.
Grayson: You sure about that? Because I don't think one kiss would be enough for you either.
Olivia: You always this smooth, or do I bring out the best in you?
Grayson: You? You make me reckless.
Olivia: I don't mind risk. Just prefer knowing what I'm getting into.
Grayson: And if I said it's worth it?
Olivia: Then I'd say you're awfully confident for someone still trying to convince me.
Grayson: Enjoy your dinner, Olivia. Don't think too hard.
Olivia: Tease.
Grayson: Only if you're impatient.
His phone buzzed in his hand as he stepped into the elevator of his New York apartment. His assistant's name flashed across the screen.
"Yeah?"
"Your meeting with the Fairchild Group has been pushed to six tomorrow evening."
Grayson let out a slow breath. That gave him a window tonight—if Olivia agreed to it.
"Got it. Anything else?"
"You have a working lunch with the Ashton firm at one, but otherwise, your afternoon is clear until dinner."
That meant a slim but possible chance to get out for a bit.
"Thanks." He ended the call and immediately pulled up Olivia's number. His fingers hesitated for a brief moment before typing.
Grayson: I know you have a busy life, but would you let me steal you for dinner tonight? I promise not to discuss hostile takeovers. And I promise not to let you win again in darts.
He smirked to himself, hitting send before he could overthink it. Olivia would either say yes or no, but at least he was putting it out there.
The elevator dinged, and he stepped into the quiet luxury of his apartment, shrugging off his coat as he checked his phone again. No response yet. He knew Olivia wasn't the type to drop everything just because he was in town, but damn, he hoped she'd say yes.
The next day was a whirlwind. Meetings stacked on meetings, discussions filled with dry financial projections, and the constant back-and-forth of negotiations. He was in the middle of a boardroom meeting, nodding as Walter droned on about the upcoming quarter's revenue forecasts when his phone, resting face-up beside his notebook, buzzed.
Olivia.
Against his better judgment, he glanced down and saw her response.
Olivia: Wow, dinner? That's a big commitment. Next thing I know, you'll be asking me to split an appetizer. Please, sweetheart, you didn't let me win; you lost because I'm a better dart player than you.
A chuckle escaped him before he could stop it, and he quickly coughed to cover it up. Heads turned in his direction.
He cleared his throat, schooling his expression into something neutral. "Continue, Walter, with the projections," he said smoothly, shifting his attention back to the monitor screen.
But even as the numbers flickered in front of him, his mind was stuck on Olivia. She wasn't making this easy. And that only made him want to chase her more.
Two more meetings followed, each dragging longer than necessary, but Grayson found himself smirking at his phone between discussions. Olivia had a knack for pulling his attention away, and he wasn't exactly complaining.
Grayson: You talk a big game for someone who barely won by two points.
Olivia: Barely winning still means I won. You don't see me making excuses.
Grayson: Is that your way of saying you'll let me redeem myself tonight?
Olivia: I don't know, I think I like having the upper hand.
Grayson: You always like having the upper hand.
Olivia: Exactly. Took you long enough to figure that out.
Grayson bit back a grin, ignoring the confused glance from his assistant as he leaned back in his chair, feigning interest in the latest market projections. He could already tell this back-and-forth was going to last all day, and he didn't mind one bit.
By the time he stepped into the elevator after his lunch meeting, his decision was made. He was done with the back-and-forth. Banter was fun, but he wanted to see Olivia. Tonight.
He turned to his assistant, George. "Book me a flight to Chicago and dinner reservations at Bavette's Bar & Boeuf."
George hesitated, shifting his iPad against his chest. "Sir, you still have meetings scheduled for—"
Grayson looked at him, expression unreadable.
George exhaled through his nose and nodded. "Understood, sir. I'll make the arrangements. Should I book a hotel for you too… or a round trip home?" He flicked his eyes up, but quickly looked back down at his screen before Grayson could answer.
Grayson smirked. "George, you'll be accompanying me to Chicago because we still need to discuss plans for the new London and Italy deals. Plus, I have a meeting with Reynolds from Dallas."
George swallowed. "Yes, of course, sir. I just assumed… Never mind. Yes, I'll get right on it."
Grayson barely nodded, already texting Olivia again.
Grayson: Hope you're free tonight. I'd hate for this flight to be wasted.
Olivia: Oh, I'm free. But just so you know, last time a guy challenged me to a "friendly" game, he ended up deleting his fantasy football team out of pure humiliation. You sure you want to risk dinner?
Grayson huffed out a laugh, shaking his head. Grayson: Well, good thing I'm a betting man. I also now have lady luck on my side and will be winning from now on.
Olivia's response came almost immediately. Olivia: Lady luck? Sweetheart, I am the playbook. And just so you know, I don't believe in underdogs—I believe in winning.
Grayson laughed, a deep, unguarded sound that filled the quiet of his office. He ran a hand down his face, still grinning as he exhaled, shaking his head in disbelief. Olivia always had a way of throwing him off just enough to make things interesting, and damn if he didn't love the challenge. Olivia had a way of keeping him on his toes, and damn if he didn't enjoy every second of it.
Still grinning, he pushed himself up from his chair, grabbing his coat from the back of it. He took a quick glance at his phone once more, as if expecting another quip from Olivia, but the screen remained dark. No doubt she was waiting to catch him off guard later.
"George," he called out as he shrugged on his coat, already striding toward the door. "Let's go. We've got a flight to catch."
George appeared in the doorway, iPad clutched to his chest. "The car is waiting downstairs, sir. I've arranged for the jet to be fueled and ready upon arrival. I also packed a bag for you with everything you might need for the trip. We'll land in Chicago with enough time for you to freshen up before dinner."
Grayson nodded, smoothing his coat as he stepped into the hallway. "Good. And just to be clear, you're not coming to dinner. You'll be staying at the hotel."
"Yes, sir?"
A smirk played at Grayson's lips. "Better brush up on your negotiation skills. The Italian attorney's don't play fair."
George sighed, following behind. "Understood, sir. I'll make sure everything is ready for your return. Enjoy your evening."
The flight from New York to Chicago was just over two hours, giving Grayson enough time to work through a few proposals with George. While his mind was split between business and the night ahead, he remained focused, discussing the finer details of upcoming deals in London and Italy. George, ever efficient, rattled off financial projections while making sure Grayson had everything he needed for the evening. It wasn't until they began their descent that Grayson finally shut his laptop, glancing out the window at the city lights below. Chicago was waiting. And so was Olivia.
Grayson stepped through the heavy wooden doors of Bavette's Bar & Boeuf, immediately greeted by the rich aroma of sizzling steaks and the low hum of jazz drifting through the dimly lit space. The restaurant exuded a timeless charm—dark leather booths, vintage chandeliers casting a golden glow, and an atmosphere that buzzed with quiet sophistication. It was the kind of place where the clink of glasses and murmured conversations blended into a luxurious backdrop, a haven from the chilly Chicago evening outside.
He had taken his time getting ready, fresh from a shower at The St. Regis Chicago, the city skyline stretching wide outside his suite's windows. The long flight, the meetings, the restless energy from his conversations with Olivia—all of it had built up to this moment. Now, dressed in a crisp, light gray suit and a charcoal-gray dress shirt with the top button undone, he looked every bit the confident businessman who didn't just negotiate deals—he won them.
But tonight wasn't about boardrooms or hostile takeovers.
It was about Olivia.
As he stepped further inside, the hostess greeted him with a polished smile. "Good evening, sir. Do you have a reservation?"
Grayson gave a knowing smirk. "Yes. Should be under Grayson Steel."
She scanned the list and nodded. "Of course, Mr. Steal. Your table is ready. Would you like to wait at the bar, or be seated now?"
His gaze flicked toward the bar—a beautiful marble counter lined with premium spirits, the kind of place a man could nurse a bourbon while waiting for a woman who loved to keep him guessing.
"I'll wait at the bar," he said smoothly. "She likes to make an entrance."
Grayson made his way to the sleek marble counter, settling onto a leather stool. The bartender, a seasoned man with a sharp vest and rolled-up sleeves, approached with a practiced ease. "What can I get you, sir?"
"Bourbon, neat," Grayson replied, tapping his fingers lightly against the polished surface. As the bartender poured his drink, Grayson let his gaze drift toward the entrance, anticipation humming beneath his calm exterior.
His phone buzzed in his pocket. Pulling it out, he saw Olivia's name flash across the screen.
Olivia: Hope you're enjoying your bourbon. Don't get too comfortable—I plan on keeping you on your toes tonight.
Grayson chuckled, shaking his head as he took a slow sip of his drink. Of course, she knew exactly where he was. And of course, she had to remind him that she was always one step ahead.
Grayson: You always do, Olivia. Should I be worried?
Her response came quickly.
Olivia: Only if you're afraid of losing. Again.
Grayson exhaled a quiet laugh, placing his phone face down on the counter. He wasn't sure if he was more entertained or intrigued, but one thing was certain—Olivia was worth every second of the wait.
And then, as if the air shifted, as if some unspoken energy signaled her arrival, the entrance to the restaurant opened.
He didn't have to turn around to know it was her.
Enchanting. That was the only word that came to mind as Grayson watched her glide toward him. Olivia was wearing a one-shoulder asymmetrical royal blue chiffon dress, the fabric flowing effortlessly around her. Her nude heels elongated her legs, and around her neck, a teardrop diamond necklace caught the dim light of the restaurant, casting a subtle shimmer with each step she took. Her thick chestnut hair had been curled lightly, giving it just the right amount of bounce as she moved, each wave framing her face with an effortless elegance.
And that smile. Damn, that smile could melt a man where he stood.
Grayson had two minutes—maybe less—to take all of her in before she reached him. But it wasn't enough time.
He took a measured sip of his bourbon, schooling his expression into something composed, but his fingers tightened slightly around the glass. By the time she reached him, he had already decided—he wasn't going to fight the pull she had on him.
Setting his drink down, he stood as she stopped in front of him. Without hesitation, he wrapped an arm around her and pulled her into a hug. It wasn't calculated, it wasn't planned. It was instinct.
What the hell was he doing?
His thoughts barely had time to catch up before his lips found her ear, his voice a low murmur meant just for her. "I told you—one is not enough for me."
As he stepped back, his hand lingered at her face, his thumb brushing over her lips in a slow, deliberate motion. A fleeting moment—one he wanted to stretch into eternity.
Olivia gave the faintest lean into his touch before straightening, her eyes flickering with something unreadable. Then, with a smirk, she echoed her own words back at him.
"And I said it sounds like that's a personal problem."
Grayson chuckled, shaking his head as he tucked his hands into his pockets, his gaze still locked on hers. "And yet, here we are. Tell me, Olivia, do you ever make anything easy?"
She tilted her head slightly, a playful gleam in her eyes. "Where's the fun in that?"
He smirked, nodding toward the table the hostess had prepared for them. "Then let's see just how much fun you plan on having at my expense tonight."
As they walked toward their table, the restaurant's golden glow wrapped around them, the rich hum of conversation blending into the low jazz playing in the background. A waiter pulled out Olivia's chair as Grayson took his seat across from her, the flickering candlelight between them casting soft shadows against her face.
She picked up the menu, but instead of reading it, her gaze flickered up to meet his. "So, tell me, Mr. Steal, was this dinner planned, or did you just wake up today and decide to fly across the country for a meal?"
Grayson leaned back, picking up his bourbon and taking a slow sip. "A good businessman always seizes an opportunity when he sees one."
Olivia raised a brow, clearly amused. "Is that what I am? An opportunity?"
He set his glass down and leaned in slightly, his voice dropping just enough to draw her in. "No, Olivia. You're the risk worth taking."
She studied him for a beat, her fingers lightly tracing the rim of her wine glass. "Flattering. But you do realize risks can go either way, don't you?"
Grayson smirked. "I do. But I've never been one to walk away from a challenge."
She exhaled a quiet laugh, shaking her head. "You really don't scare easy, do you?"
"Not when I know the reward is worth it."
The waiter arrived then, interrupting the charged moment between them. "Have we decided on dinner, or would you like a few more minutes?"
Olivia looked at Grayson before closing her menu and handing it to the waiter. "I'll have the filet, medium rare. And I'll trust your sommelier's recommendation for a pairing."
Grayson handed his menu over as well. "Same for me. And another bourbon."
As the waiter stepped away, Olivia rested her elbow on the table, chin propped against her palm. "So tell me, Grayson, since you're a man who never walks away from a challenge, what exactly is your endgame here?"
Before he could answer, their meals arrived. The plates were set before them—her filet, perfectly seared with a side of buttery mashed potatoes and roasted Brussels sprouts, and his, nearly identical, the aroma rich and mouthwatering. The sommelier returned with Olivia's wine, pouring a deep ruby-red glass of Bordeaux, its scent laced with dark fruit and spice.
For a moment, the conversation paused. The only sounds between them were the soft clinking of silverware and the occasional murmur of diners around them. The silence wasn't awkward, but it left Grayson in his own head.
Had he said too much? Olivia was unpredictable—one second teasing, the next unreadable. He still didn't know where he stood with her. And now she was just… eating. Expression neutral, not giving him a damn thing to go on. Her poker face? Flawless.
He cut into his steak, chewing slowly as his thoughts tangled. He had handled multi-million-dollar deals with less hesitation than this dinner.
Finally, clueless on where to go from here, he cleared his throat. "Umm… how's your wine?"
Olivia looked up at him, her brow arching slightly as an inquisitive expression crossed her face. "My wine?" she repeated, as if tasting the words, then blinked. "Umm… it's great, thank you?"
Then, just like that, she started laughing. It began as a soft chuckle, the kind that bubbled up unexpectedly, but soon turned into a full, rich laugh that had her tilting her head back slightly. Her shoulders shook as she covered her mouth, clearly amused by his sudden awkwardness.
Grayson, caught between confusion and intrigue, watched her with an amused smirk of his own. "I feel like I missed the joke."
Olivia shook her head, still giggling as she leaned forward, resting her chin on her hand. "You? Mr. Always-in-Control, Grayson Steal, are so thrown off by a dinner conversation that the best you could come up with was asking about my wine?"
Grayson exhaled a short laugh, shaking his head. "Well, you're not exactly easy to read. I was trying to gauge if you were enjoying yourself."
She grinned, swirling her glass slightly before taking a sip. "I am. But I have to say, watching you squirm for once? That might be my new favorite part of the night."
With a twinkle still in her eye, Olivia leaned back in her chair. "If we're going to have a real talk, I need dessert."
Grayson smirked and signaled the waiter over. "You heard the lady. Clear the plates, and bring us one of everything from the dessert menu. We must try everything, right?"
The waiter blinked, then quickly masked his surprise with a polite nod. "Of course, sir."
Olivia's smile widened as she rested her chin on her hand. "I couldn't agree with you more."
The moment settled, the flickering candlelight dancing between them. As they waited, Grayson found himself watching her—not just the playful glint in her eyes, but the way she carried herself, the effortless confidence that made it impossible to look away.
He leaned forward slightly, his voice softer this time. "You are beautiful, you know that, right?"
She blinked, caught off guard for the first time that evening. A flush of warmth spread across her cheeks before she offered a soft smile. "Thank you."
But Olivia, ever sharp, wasn't about to let him off so easily. She picked up her wine glass, taking a slow sip before leveling him with an expectant gaze. "Sir, let's not forget my question from earlier. What is your endgame?"
Damn it. What was his endgame?
If this were business, he'd know exactly how to close the deal. He would have already analyzed every variable, predicted the obstacles, and maneuvered his way to a win. With women? That was even easier. A night of mind-blowing sex, a few weeks of indulgence, and then parting ways on good terms. He never pursued. Never chased.
But Olivia wasn't part of the equation. She didn't fit into a formula.
And worst of all? He was the one chasing her.
Marriage? No. Not again. Not after Sasha. He had no interest in returning to a place where promises were broken, where love turned into strategy and every moment felt like a calculated move.
But Olivia… she was different. She was unpredictable, impossible to pin down, yet here he was, sitting across from her, desperate to know what was going on inside that sharp, beautiful mind of hers.
And now? Now she was just eating her dessert, her poker face flawless.
Grayson exhaled through his nose, then leaned back in his chair, watching her carefully. "You don't make things easy, do you?"
Olivia smirked over her spoon. "And here I thought you liked a challenge.""