A/N: I was completely blown away by the response to the first chapter. Thank you so so much to everyone who read/reviewed/shared, I really do appreciate it. It makes me even more excited to finally commit to and post this story. As always, I hope you enjoy and let me know what you think.

"Babe, I need you to slide over a little more."

"Babe? Olivia."

Two Days Earlier

"I'm telling you, Abby, if he doesn't stop trying to control everything all the time, he's going to give himself a heart attack – or at least a pretty bad ulcer." Olivia readjusted the phone sandwiched between her shoulder and ear, leaning down to remove her heels.

"Well, that's Cyrus for you." Her friend spoke with a mouthful of what she could only assume to be something sweet and fresh out of the oven. "At least now he has you to ease some of the burden."

"Oh joy." She rolled her eyes playfully. "Let me know if it starts looking like I might blow steam out of my ears at any given second."

"You mean like anytime you're in a room with a certain someone's parents?"

She groaned, sinking back into the couch. "Please don't mention it, or them – or him."

"Sorry," Abby mumbled, and Olivia could practically see the insincere grimace pasted on her face. "Should we talk about another certain someone? Your good friend from the bar, perhaps?" She asked.

Olivia tried pointlessly to stop the wistful smile that tugged at her lips at the mere mention of him.

Fitz.

He was…amazing. She had been struck by his laughter first, and his good looks second. He was a gorgeous mass of man, with a strong build made even more captivating by his well-fitted suit. She had tried hard not to stare, but that damn stray curl falling just above those beautiful blue eyes made it entirely too difficult.

His voice was deep with a near dreamlike quality, lulling her into a heavier daze of attraction every time he opened his mouth. And the conversation between them was so easy. They didn't get too personal, but it certainly felt like they had. She didn't even know his last name, and yet it was as though they had been friends for years.

And when he touched her – the way he touched her – it made her feel alive in a way she had never known to be possible. It was thrilling, and overwhelming, and so unbelievably satisfying…

"Liv? Hello?"

She shook her head to clear her thoughts. "Sorry, I'm here."

Abby let out an amused laugh. "I see he's still got you all worked up."

"It's just…" she considered her words for a moment. "He was…special."

"Obviously," Abby responded immediately. "He must've been if you almost fucked him in the bathroom of a bar."

Olivia laughed despite herself and pinched the bridge of her nose. "I don't even know what happened. One second we were talking, and the next – it was like all this tension just exploded, and it felt…right. Is that weird to say?"

"No," Abby spoke with another mouthful. "Which is why I don't understand why you ran out, instead of grabbing his sexy ass and running to the nearest hotel."

Olivia sighed. She had been turning the moment over in her mind ever since it happened. That night, she battled several hours of restlessness before finally grabbing a glass of her favorite red to put her mind and body at ease. She woke up with a headache and a dazed sense of disbelief about the night before.

She mulled over it for two days when yet another dream of him led her to bare her soul to her best friend. There were simply too many emotions to work through on her own – guilt, regret, longing.

"I told you," she spoke lowly, as if sharing a secret not intended to fall on too many ears. "Something reminded me of Dean, and I just, I couldn't do it."

Abby huffed. "Even after all those hours we spent getting you ready. You were supposed to get laid, Liv, remember?"

She did remember. It had been a little over two weeks since she was last in direct contact with Dean, and, sensing her friend's growing annoyance at his constant attempts to reach out to her, Abby deemed that Friday Olivia's "one day for a one night stand." After much arguing and resistance, Olivia agreed, acknowledging that it had been far too long since she had a fun night out just for herself.

She had decided to take the name Alex for the night as a final, innocent deviation from the usual. For just one night, she wanted to pretend – pretend that her personal dealings didn't give her regular migraines, that she didn't feel as though the world was constantly resting on her shoulders, and that all she needed from life was smooth liquor and a handsome stranger.

But things with Fitz felt real – too real, and he made her not want to pretend anymore. It was what had driven her to share her real name and to act more recklessly than she had since college. In that moment, she truly wanted him with everything in her.

But then he pulled out that handkerchief, and all she could see was Dean, and she was instantly flooded with guilt.

Though things hadn't ended on good terms by any stretch of the imagination, there seemed to be so much unfinished business between her and Dean. He had visited her apartment more than once, called regularly and left sad, desperate phone calls begging for her attention. And even through all her anger, she couldn't help but feel bad for not giving him the time of day.

Yet, admittedly, when she woke up the morning after, still in a fog of semi-recovered memories, she hadn't felt nearly as bad on his behalf as she did for Fitz. It seemed unfair to tangle him in the messy affairs of her personal life beyond that night. And something told her if they had gone any further, they would have had much more than one shared night between them.

"I honestly think you should just tell that man to fuck off," Abby continued after a moment. "Especially after how he's acted in the past two months alone."

Olivia closed her eyes, knowing immediately where this conversation was going.

"I mean, he spends weeks trying to talk you out of taking a promotion you worked your ass off for, and for what reason? Because he thought it'd be 'too much to handle' – bullshit!"

Olivia jumped as she yelled into the receiver.

"He didn't want you to take it because between his parents' outdated beliefs and his own ego, he couldn't take that you'd be making almost just as much as him. And then when Daddy handed him the keys to the kingdom, and he realized you had no intention of being Suzy Homemaker, he proposed in front of all his pretentious, fuddy-duddy co-workers just to show off how much of a 'power couple' you'd be – after you told him you weren't ready to get married, might I add."

Just the reference to the incident, alone, made Olivia roll her eyes.

It had been a complete mess of a night – an office party turned full ambush when her oh-so-lovely boyfriend of just over two years got down on one knee.

She originally thought it odd when he suddenly become so proud to share her newly acquired position during the night. She hoped it was because he finally got his head out of his ass and stopped swimming in the shit stream of his father's particularly unbearable brand of misogynoir.

But then, as he pulled out a ring and made some grand speech about their years in college together, their reconnection just a few years earlier and their currently rising business prospects – especially with her handling Red Giant Jets' very own PR account over at her firm – she knew exactly what he was doing. He was making a spectacle of their relationship and turning it into a chance to boost his own image. He was proving a point to investors and to the few particularly defiant brown-nosers who had dared to question his adequacy following his recent appointment to CEO in the wake of his father's retirement.

Of course, his naysayers hadn't been entirely wrong, given that his father would still be running things; only this way, he'd get to do so from whatever island he ran off to with his wife (or one of his several mistresses), while his precious son would finally get to put that barely-earned business degree to use. And if said son was to share a marital bed with a direct line to one of the company's most important assets, well, there couldn't be too much said of his powerlessness.

When he finished speaking and all eyes fell on her, she found herself too shocked and too embarrassed to deny him. She nodded silently, tears of anger – mistaken for those of joy – building in her eyes.

She welcomed any and all congratulations with as much sincerity as possible, and mustered up enough of a farce to engage with Dean throughout the rest of the night. However, the moment they slid into their Uber, the smile fell and she could immediately feel her face heat with rage.

She still didn't entirely remember everything that was said, but she did recall the look of embarrassed shock on his face and amusement on that of their driver. They pulled up to her apartment not a moment too soon, and she threw the ring at him, slamming the car door in his face without looking back.

"I don't know, Abby." By now she had removed her blazer and tucked her feet under her legs to settle further into the couch. "We've been together for almost two-and-a-half years, and to just throw that away after one fight?"

Abby scoffed, and Olivia knew it sounded just as ridiculous to her as she thought it did the moment it left her own mouth.

"That wasn't one fight, Liv. That was every fight – every problem you guys have had since you first started dating, every reason why you don't want to marry him."

She knew this to be true, and yet, she couldn't bring herself to just consider that the end of them. She had invested far too much time and energy into making sure they stayed afloat for it all to sink at once.

When she didn't respond, Abby groaned into the receiver.

"One date."

"What?" Olivia scrunched her eyebrows in confusion.

"Agree to go out on one more date with him, and if things don't go well, you end it officially, for good."

She nodded at the idea. It was good, and seemed like a fair enough solution to everything.

"Ok," she agreed. "One date."

Present Day

"Mathew told me to try the salmon, but I was thinking of the – Liv?"

She snapped her head in his direction.

"Huh?"

He grinned. "You ok? Or have I lost my touch already?"

Though his words were playful, she could see the nervousness behind them. He was genuinely trying, but she still couldn't bring herself to give him her full attention.

She had spent the last twenty minutes staring out the window, her mind running a mile a minute – all the while, he attempted valiantly to navigate the rough waters of polite, if not slightly tense, conversation.

"No, no you're good." She smiled, figuring she could at least give him that much. "This is nice…I think I might actually try the salmon."

He nodded and returned his attention to the menu, while her eyes drifted once more to the window.

She wasn't sure where he had gone after they got out of the car, but something in her hoped to spot the black Lincoln, and more importantly, to spot him in the driver's seat.

She had been in complete shock when she met the gaze of a familiar pair of blue eyes through the rearview mirror, her own eyes practically burning a hole in the back of his seat during the ride to the restaurant.

She and Dean shared pleasantries in the backseat – her words failing her more often than not – and he eventually took to recalling random stories he had heard from coworkers since their last time together. But she barely heard any of it. She was entranced instead by the profile that had started to appear regularly in her dreams, by the trimmed curls that had slipped seamlessly between her hands, by the calloused fingers gripping the steering wheel that had fit so perfectly –

"We'll take your finest bottle of Pinot Blanc."

She blinked, once again bringing herself back to the present moment.

When the waiter retreated, Dean folded his hands and leaned onto the table.

"So how have you been, Liv, really?"

She looked away, smoothing over the napkin on her lap before answering, "Like I said, I've been good."

"You forget how well I know you." He looked at her pointedly. "You've been distracted all night, and you didn't even listen to their wine selection. So what's wrong?"

His remark made her smile briefly, and she finally met his gaze. "I just have a lot on my mind right now."

He nodded. The waiter returned to fill their glasses, and as they ordered, she could feel his eyes still focused intently on her.

When they were alone again, he raised a single brow and asked, "Is it the job? Is it too much for you?"

And there it was.

She glared at him. Hard.

He immediately leaned back, swallowing thickly.

"I'm sorry, I shouldn't have – you said you hated when I did that, and I'm sorry."

Her gaze softened and she crossed her arms, inviting him to continue.

"I was listening to what you said that day, Liv. Really, I was, and you were right about all of it…" He tugged on his ear, a telltale sign that he was actually nervous. "I should be supportive, and not just when it benefits me. And I was wrong that day to pull the stunt I did – but I do want to marry you, just…when you're ready."

She nodded. It was certainly a step up from his past apologies, usually a string of mildly apathetic variations of "Babe, I'm sorry, ok?" followed more often than not by a company-issued gift basket or – when things got really bad – something expensive with lots of diamonds.

He sighed, and she knew he could tell she still had a foot out the door.

"I've screwed up a lot, I know. But, Liv," he was pleading now, his eyes wide, "I don't know how to do this thing without you by my side. I can't – I don't know how to function when there isn't an us. These past few weeks have been worse than finals junior year."

She was moved by his earnestness and allowed herself to giggle softly at the memory.

"I had the flu, you had food poisoning and Cheryl sent us the wrong study sheet."

"I swear, if you didn't have those professors in the palm of your hand –"

"I still would've been fine, but you might've graduated a semester or two late," she finished, and they fell into easy laughter for the first time in what seemed like forever.

He was smiling when they quieted, and she could feel her guard start to let down.

"I don't know what I would've done back then without you."

She shrugged. "Simple. You would've failed."

They laughed again, finding humor in the truth of her statement.

During their days at Georgetown, sometime after she had completely decimated his argument during the first week of intro philosophy, he had taken up a one-sided rivalry against her. However, when it became obvious he wouldn't get anywhere trying to best her, he decided to instead seek out her help. Though she was known to be the youngest in their class by two years, she had one of the sharpest minds, and her tutoring lifted his tragic GPA, saving him from inevitable failure and wasted tuition money.

At first, she was entirely unimpressed by him. She was young, smart, and fiercely independent – a necessity following her mother's death several years earlier. She had no time for air-headed sons loaded with far too large trust funds to carry them through life, especially not ones who tried pathetically to challenge her.

But then, when she relented and began tutoring him, they started spending extensive hours outside of class together. And even amidst all her academic aspirations, she was still a young woman who appreciated attractive young men; and Dean Shaw, with his chiseled jaw, and sandy brown hair and hazel eyes was a sight for sore eyes.

They became good friends, surprising almost everyone in a ten-mile radius who knew anything about them. As it seemed, the law stood that opposites attract. She was studious, determined and every professor's dream; he was unpredictable, unfocused and a ball of explosive energy. She taught him to study, and he introduced her to an impressive array of liquor. She helped him keep his head out of the clouds – or from in between a girl's thighs – when midterms came around, and he warded off the ever-present flock of guys vying for her attention, citing always as an excuse: "They're too old for you, babe."

Things were fun with Dean. By junior year, they were best friends, best flirty friends who always seemed to teeter on the edge of something more. But then graduation came the next year, and they lost contact and that was the end of that.

That is, until they ran into one another at a work conference in Kentucky of all places. They spent hours catching up and became so wrapped up in their conversation that she missed her late flight back to New York. Upon learning that they both shared a home state, he promptly invited her to ride with him on the private plane he had borrowed from his father's company – the same company he was looking to take over in the near future.

He spent much of the flight commenting on how excited he was to be reunited with her, how he believed fate was giving him a second chance. And then, finally prompted by her curious gaze, he admitted that he had been in love with her for who knows how long during their time in undergrad. He continued, admitting that nearly every month of their senior year he swore he would ask her out, and every month he chickened out until it was too late.

She was shocked, to say the least, and eventually admitted her own infatuation with a laugh and a shake of her head.

"I would've said 'yes' if you asked, you know. I liked you, too… a lot."

His face lit up immediately, and he didn't waste a second, asking her out right then and there.

She was surprised again by his forwardness and told him she'd think about it, grateful the plane had just begun its descent. They exchanged numbers, and in true Dean fashion, he hunted down her apartment and sent her flowers every day for nearly two weeks before she finally relented, and the rest was history.

At the time, she loved how being with him made her feel – like they were back in his dorm, eating cold pizza at 2 a.m., imagining all the possibilities that lay ahead at daybreak. But, as time went on, his youthful charm started to seem more like masked immaturity, and she found herself wondering if, at thirty-four, he was really any different than he had been at twenty.

"Alright, here we go." Their waiter returned, placing their food down on the table. "Enjoy."

Dean didn't bother looking at his plate, his attention still focused solely on Olivia.

"Liv," he reached over the table, taking her hand in his, "I know I don't have a right to, but I'm just asking for one more chance."

His face was serious, his voice desperate and she considered him for a long moment, a surge of emotions rushing through her.

He was an absolute idiot at times, and a complete pain in the ass when he wanted to be, but this was Dean, her Dean – the first real friend she let in after things like death and abandonment had stolen her innocence and hardened her to life. And as her longest relationship to date, he was one of the only constants in her life.

So why, as he was laying it all on the table in hopes of holding them together, was she so tempted to say no? Even worse, why was she still fighting off thoughts of a pair of piercing blue eyes and an enticingly deep baritone voice?

"Please, Liv," he begged once more. "I meant what I said that day on the plane. I love you, and I'll do anything it takes to show you."

She took in a deep breath and closed her eyes, trying to focus only on the here and now.

"Liv?"

"I'm so sorry about this, Liv. Are you sure you don't want me to tell them I can't come in?"

She smiled sympathetically at his worried expression.

"It's ok, I promise. Besides," she paused as he opened the car door for her, "I like to see you taking care of business."

He grinned, following her into the car.

"You do?"

She nodded, biting down on a smile as he wiggled his eyebrows playfully.

"Well maybe I can show you how I take care of other business…"

The sound of a throat clearing interrupted them, and she could almost immediately feel her body go rigid with realization.

"Where to, Mr. Shaw?"

She looked up, meeting his eyes once again in the rearview mirror, his stare hard and locked intently on her.

"Oh, I need to head back to the office to take care of a few things, but can you drop Liv off afterwards? Thanks." Dean placed his arm around her shoulder and leaned into the seat.

As they pulled off and made their way to his office, she found herself unable to relax into his touch. Back in the restaurant, when she agreed to give them another go, she tried her best to be fully present with him. By the time he received an emergency call on his work phone, things almost felt normal between them again.

Almost. Because, as Dean encouraged her to try some of his meal, her mind drifted off to thoughts of a glass of scotch replacing her bourbon – of the thrill of tasting that same scotch on Fitz's tongue an hour later. And because, as Dean ran a hand through his hair, she realized she had never felt compelled to reach for it in a moment of passion, like she had with Fitz.

And even now, as she sat with Dean, she could feel Fitz's presence filling the space between them. It was impossible to ignore, and she could sense the sinking feeling of regret settling in the pit of her stomach.

"I don't know how late I'll be there, but I think I might stay at Dad's penthouse," Dean spoke.

She knew he was waiting for her to invite him over to her place…or to invite herself over to the penthouse. But, aside from being in no mood to actually sleep with him any time soon, she couldn't deny that spending the night with him in any capacity felt wrong.

And agreeing to do so in front of Fitz felt especially like betrayal.

She shook her head at the thought. Logically, she knew it didn't make sense; she had only known him for a few hours, and they were two consenting – and, at the time, single – adults who had engaged in what was little more than a romp easily rivaled by most teenagers.

Yet, somewhere in the back of her mind, she also knew it certainly felt much more serious than her tryst with Jonah Elliot at boarding school, and more intense than anything she had experienced with Dean.

"Do you wanna go out for breakfast in the morning?" He questioned when she didn't give him the response he was looking for.

"I can't," she replied before she could even remember why. "I'm…meeting Abby. We're brainstorming new promotional plans for the bakery."

"Oh." She didn't miss the slight annoyance on his face at the mention of her best friend. "Well, what about lunch, or maybe dinner?"

She was relieved when the car came to a stop in front of his office.

"I'll let you know," she offered as an answer.

Just as he started to get out of the car, he turned to peck her lips.

"See you later, babe."

She fought the urge to wipe her mouth, growing embarrassed as she realized Fitz was watching them through the mirror.

The air shifted immediately once the door closed, and she willed herself to look at anything other than him. He, on the other hand, turned so that he was looking directly at her.

"Home, Ms…"

His prompt encouraged her to finally meet his gaze.

The moment she did, she sighed. "Fitz."

"You can call me Mr. Grant, Ms. –"

"Pope," she finally finished, admittedly thrown off by his professional demeanor.

He nodded. "So home, Ms. Pope?"

She sighed again and turned to look out the window. "Yes, please."

The ride was unbearably tense, so much so she considered walking the rest of the way after only ten minutes. Her eyes drifted to him often. She took in the slight clench of his jaw, the way his fingers seemed to grip the steering wheel extra tightly. And at nearly every red light, she found that – despite herself – she'd look for his eyes in the rearview mirror. Not once was she disappointed.

When they were only a block away, she couldn't take the unease any longer.

"Fitz, look –"

He cleared his throat, and she rolled her eyes.

"Mr. Grant, I just wanted to say that you and I last Friday, and now this, it isn't…" she couldn't find the words. It was a first for her. She always knew what to say, and when to say it. It was what made her so brilliant at her job.

But being here with him, with so much tension weighing down on them, she had no clue how to approach the situation.

"It's fine, Oli – Ms. Pope," he corrected himself. "We're both adults, and you did say things were complicated, so I'd appreciate if we could just move past our…brief history, and keep a strictly professional relationship…" He trailed off, and she couldn't help but notice how unconvinced he sounded by his own words.

But as he pulled in front of her building and turned to her with a look in his eyes that seemed so much like defeat, she knew she'd agree to whatever he thought was best going forward.

"Ok." She nodded with a small, friendly smile that didn't quite mask her displeasure. "Thanks for the ride." Just as she pushed open the door, she heard him sigh, and she paused, not entirely sure of what she hoped would happen next. Finally, when he didn't say anything, she glanced at him one last time before getting out. "Have a good night."