A/N: Hi! So I've been working on this for a while and I'm really proud of it. It was inspired by a couple of things and I hope everyone enjoys it.

August 1999

Olivia hummed along with the jukebox as she sliced an apple pie in preparation for the dinner service. The bell above the diner's door dinged and she turned around to greet the customer, but stopped with a smirk at the sight of her best friend Quinn. Quinn grinned as she took a seat at the counter. "I didn't receive my rousing Philly's greeting."

"You can give my ass a rousing kiss," Olivia replied.

"Someone's cranky."

Olivia frowned. "I was looking at my calendar today and it's been three months since I've been on a date."

"Well you did just get out of a relationship, Liv."

"Jake and I broke up four months ago. And I know it took me a few weeks to get over it, but I thought by now I'd have at least rebounded."

The bell jingled and a customer, a dark-haired man who ate at the diner every day on what Olivia assumed was his lunch break, entered. He smiled as he sat down and Olivia walked over to pour him his usual mug of coffee.

"Hi," he said with a smile.

"Hi. What'll it be today? Meatloaf or Pork chops?" Olivia poured milk into his coffee then added four sugars, remembering exactly how he took it after seeing him every day for two months.

"I'd like to see a menu today. You know I've gained like ten pounds since I started eating here?"

Olivia smirked. "I've actually lost weight since I started working here. I can't even look at a pie without cringing."

She retrieved a menu from the back counter then went back to Quinn. "I can find you a rebound if you want."

Olivia shook her head. "I'm not actively looking for a rebound. I just want to go on a date."

"Well you're not my type if this is your way of dropping hints," Quinn replied.

"Shut up." She walked back to the other side of the counter and smiled at her customer. "Know what you want yet?"

"I think I'll have the chicken and dumplings, with green beans and cornbread," he answered. "And a date if you're giving them out."

"That's not really a healthier alternative to what you've been getting." She smiled, wrinkling her nose. "And we've been over this. You only wanna date me because I serve you food in this ridiculous apron."

Fitz smiled. "That's not true. And even if it was, you can't prove it until we've been on at least one date."

Olivia laughed as she walked away to put his order in. She blinked at Quinn's frowning face. "What?"

"How can you whine about wanting a date then turn one down two seconds later?"

"You don't know the whole story."

"What's the whole story?" Quinn asked then turned to Fitz. "Hey, what's the matter with you? Are you married?"

Fitz smiled and shook his head. "No."

"Do you have a small country of children with a dozen different women?"

He laughed. "No."

"You into My Little Ponies or something?"

He laughed harder, shaking his head. "No. I'm into imported beer and college football, but that's about it."

Quinn nodded and turned back to Olivia. "He seems normal enough. Why not him?"

Olivia shook her head. "I think we'll be okay maintaining our relationship as waitress and customer."

Quinn looked at Fitz and threw her hands up in surrender. "It's just as well. She's crazy anyway."

The cook rung the bell signaling that Fitz's food was up and Olivia went to the window to retrieve it then set it in front of him. "Eat up."

Fitz ate his lunch, reading The Wallstreet Journal, and Olivia went on about her work, checking in with him once in a while. "Need anything else?"

"Just the check, and your phone number," he answered with a smile.

Olivia smiled as she shook her head. "One check coming up."

He shrugged. "Had to try one more time."

She brought him his check and Fitz gave her his credit card then signed the receipt she brought him. He smiled as he placed her tip under his coffee mug then stood. "See you tomorrow."

"Bye," Olivia replied then went to collect his dishes. She picked up her tip and smirked at what he'd left. She shook her head at the $1000 check, made out to "Olivia, the beautiful brown-eyed waitress," with his phone number written in the subject line. She took it back to Quinn and showed it to her. "This is the kind of person you want me to date."

Quinn laughed. "It's cute."

Olivia rolled her eyes as she folded the check and tucked it in the pocket of her apron.

xxxxx

Later that evening, after they'd returned to their apartment, Quinn brought up Fitz again. "So are you gonna call him?"

"No. Why would I?" Olivia asked.

"Because you kept the check with his number on it."

Olivia shook her head, scooting over on the couch to make room for their neighbor Stephen as he walked toward them. He sat on the couch and passed her the bowl of popcorn. Quinn looked at him for help. "Stephen, tell Liv she needs to call this guy that's after her. She's been whining about wanting a date forever, and he wants to take her out."

Stephen looked at Olivia. "What's wrong with him?"

Olivia shrugged. "He just doesn't give me that crazy butterflies in my stomach feeling."

"Because that's so reliable," Stephen muttered.

Olivia took the check from her purse and handed it to him. "And because he thinks this is cute."

Stephen took the check and smirked at it. "It's clever if nothing else… Wait, Fitz Grant...where do I know that name from? Fitz Grant, Fitz Grant, Fitz Grant… Hold on."

He held up one finger then darted out of their apartment across the hall to his own. He returned a moment later with his newspaper and flipped through it then held the paper up in front of Olivia's face. "Is this him?"

Olivia looked at the picture on the newspaper's business section and nodded. "Yeah."

Stephen blinked at her. "You just turned down a date with a millionaire."

Olivia's eyes widened and Quinn's jaw went slack. "What?"

"His father designed ProTools 360. Every office in the country uses it. Fitz just completely streamlined his father's design. He made four million dollars last year," Stephen answered.

"Oh my god," Quinn whispered, picking up the check. "This is a real check. This is unbelievable."

Olivia frowned as she took it. "Unbelievably insulting."

"Not to defend what may have been a down payment for some very extravagant sexual favors," Stephen interjected, "but when the check was worthless you thought it was cute, Liv."

"I said he thought it was cute." She scowled at the check. "What is this supposed to mean? What did he think I would do with this?"

"Not to suggest taking money that may consent to some very extravagant sexual favors," Quinn interjected, "but that could go a long way at Saks' annual sale."

Olivia looked at the check, tempted to cash it, but shook her head. "Tomorrow I'm gonna track him down and give it back."

"I totally respect that, but what if you cashed it then gave the check back. It's the check that's insulting, not the money, right?" Quinn proposed. "And it's almost winter. Tell me a pair of Jimmy Choo boots wouldn't take the sting out of the insult?"

"Absolutely not." Olivia shook her head again.

XXXXX

The next day Olivia found the headquarters of Protools 360 Inc. in the middle of Manhattan. She was surprised at the ease of getting to his office on the top floor. A long-legged redhead sat behind a glass desk, her head bowed as she wrote on a yellow legal pad. She wasn't the tight-sweatered blonde bombshell Olivia was expecting of such an office, but she was striking nonetheless. Olivia walked over to the desk and she looked up. "May I help you?"

"I need to see Mr. Grant immediately. Is he in?"

"May I ask what this is about?"

"It's very private. Just tell him Olivia Pope is here."

The woman raised her eyebrows but pressed the call button on the intercom. "Mr. Grant, there's an Olivia Pope here to see you. Shall I send her in?"

There was a moment of silence on the other end before his voice came through. "Um, yes. Right away."

The redhead looked up to tell Olivia she could go in but Olivia was already at the door. She entered his office and frowned at him smiling as he leaned against his large mahogany desk. She pulled the check from the pocket of her short overalls and held it up. "Do you want to explain this?"

He continued smiling and gave a boyish shrug. "I never know how much to tip. Plus, it got me a chance to see you again."

"One, you're supposed to double the tax of your total. And two, I'm not here to see you. I'm here to scold you." She looked down at the check then back at him. "What were you thinking?"

"Well I know you work for tips, and I know New Yorkers are typically unreasonably demanding but rarely generous, so I figured it'd be a nice gesture. And I also figured you'd take it the wrong way and find me to take our relationship to the next level."

Olivia blinked at him. "And what level is that?"

"Well yesterday you said we were just customer and waitress. Today we're this couple having a really big fight."

She didn't want to, but Olivia laughed, covering her face as she shook her head. "You are completely ridiculous."

Fitz smiled. "There's a certain charm to it, isn't there?"

"I'd like to say yes but I don't want to encourage this kind of behavior," Olivia replied.

"You know how you should punish me? You should make me take you to dinner and pay for it. I'll even pick you up. And it'll be at a really inconvenient time like tomorrow night at 8."

Olivia smirked. "I'll agree only if you take this check and destroy it, and promise me you'll never do anything like that to another woman."

"Well I've already done it to you. I don't think there will be any other women, but maybe that's just wishful thinking." He smiled sweetly, stuffing his hands in his pockets. "And I think you should keep it as a memento."

"A memento of what? The time you terribly offended your way into a dinner date?"

"Why don't you cash it? Buy yourself a first date outfit."

Olivia looked down at her $20 overalls over her white baby tee from the Gap. "How much do you think I spend on clothes?"

Fitz shrugged. "I'm just assuming women's clothes are ridiculously expensive."

"That's true but I don't want your money."

Fitz shrugged. "Well I'm not taking it back. And I'm going to have Abby call Bloomingdale's to tell them you're coming."

"Bloomingdales? You really don't know how much I spend on clothes." Olivia laughed. She was more of a consignment store girl, but the prospect of shopping at Bloomingdale's piqued her interest.

"Well now you've got the money. Live a little."

Olivia wanted to argue but she didn't have anything to say. She tucked the check in her purse then left the office building.

xxxxx

After leaving the bank, Olivia took a cab to Bloomingdale's where she was surprised to find a salesgirl waiting for her. She was a tall brunette with large teeth displayed in a saccharine smile. "Olivia?"

"Yes?"

The woman's already large smile broadened. "I'm Mellie. We've been expecting you."

Olivia continued to smile. "Mr. Grant's assistant called."

Mellie nodded, her smile twitching. "She said you were his niece."

Olivia snorted as she followed her to the evening wear section. "He's not my uncle."

"They never are, dear," Mellie replied with a knowing smile. "So what do you need an outfit for?"

Olivia shrugged, looking around at the elegantly dressed mannequins. "I don't know. What do you wear on a date with a millionaire?"

Mellie turned to look at her. "I think you're a Diane Von Furstenberg kind of girl."

Olivia shrugged again. Diane Von Furstenberg sounded like a designer her mother would wear, and she was momentarily saddened that she's left Quinn at home as her label-conscious friend would have definitely been helpful. "Sounds cool."

Mellie went to the rack holding the dresses and picked out three: one black, one deep red, and one jade. "You look like a size 4."

"I'm usually a 6," Olivia corrected.

"Nonsense," Mellie replied, handing her the dresses. "I think we'll try these first. If they don't work out, we've got some new DKNY that I've been itching to try on someone. Now put these on, while I pull the DKNY and get Liz in shoes to start looking. You're a 7?"

"Yes," Olivia replied, somewhat in awe of the woman's enthusiasm. She went into the dressing room and took off her overalls then slipped on the jade wrap dress. It was long-sleeved and fell just below her knees, patterned with pink blossoms. She frowned at her reflection then took the dress off and put on the black one. It had three-quarter length sleeves and stopped above her knees. She liked it better than the first one but couldn't deny that the look wasn't her style. She poked her head out of the dressing room, relieved to find Mellie there waiting. "I don't think these are my style."

"Alright. Let's talk more about your style. What do you like?"

"Sundresses and Keds, t-shirts and miniskirts, turtlenecks. I love overalls, long, short, or dresses. I really like plaid, and denim shirts or vests." She stuck her foot out the door. "And of course, my Birks."

Mellie looked down at the sandals and her heavily made-up face crinkled but she quickly regained her salesman veneer and nodded. "Okay, so very girl next door. We can do that. We'll get you a nice slip dress—very popular right now—and some heels."

"And maybe a jacket? I don't know what we're doing so I should probably be prepared."

Mellie chuckled as Olivia shut the door. "Oh honey, you don't wear a jacket on a date with a man."

Before Olivia could ask why she wouldn't wear a jacket on a date with a man, she heard Mellie's footsteps moving away from the door.

The next few hours were a flurry of activity, with Mellie scouring the racks for the perfect dress, which ended up being in the juniors' department. It was a black leather dress with a flouncy hem. Olivia would never have picked it out for herself, but Mellie was overjoyed at the find. She had Liz find Olivia nude pumps then shipped Olivia off to the cosmetics counter.

When she got home, the phone was ringing. She set down her shopping bags then went to answer it. "Hello."

"Hi." A smile spread across her face at the sound of his voice. "I hope you don't mind but your friend left your number at the diner for me."

"I don't mind. Now I get to use your check as bail money after I kill her." She smiled when he laughed. "I was just calling to see if you liked French food."

"It's okay," Olivia replied.

"Italian?"

"Too much cheese. I'm lactose intolerant."

"Seafood?"

"I'm more of a greasy Chinese girl, Mr. Grant."

"I can do greasy Chinese. Any other requests?"

Olivia smiled. "Wear that cologne you had on earlier. It smells nice."

"Can I make a request?"

"Tread wisely, Mr. Grant."

He laughed. "While I'm sure there are very few things you do that are unattractive, those shoes you had on today were really ugly."

Olivia looked down at her black leather Birkenstocks. "Really? These are my favorite shoes in the whole world. I've had them since high school. These shoes graduated with honors from Spelman."

"Really? What did they major in?"

"English. Well specifically writing for television and popular periodicals."

"Anything I've seen?"

"Yes. I'm a secret billionaire working in a greasy diner to break up the boredom. Who knew we had so much in common?"

Fitz laughed. "You know one of my old lacrosse buddies works at CBS. I could get you a meeting if you want."

"Oh yeah. That's the story I want to tell Glamour magazine someday. My billionaire boyfriend had an in at CBS and now I'm the queen of primetime."

"So I'm your boyfriend?"

Olivia laughed. "Shut up. I can hear you smiling."

"That wasn't a no."

"It's not a yes either."

"Well the night's not over."

"It hasn't even started." She smirked when he didn't reply. "What? I can hear you smiling."

"I'm really excited to see you tonight." He chuckled. "I just lost all my cool points, didn't I?"

Olivia laughed. "Not until you used to phrase 'cool points.'"

"It's not like you have much high ground. Look at your shoes."

Olivia laughed again. "Shut up."

They flirted for a few more minutes before Fitz had to go to take another call.

XXXXX

It was after 10 when Fitz buzzed Olivia's apartment. She started awake, having dozed off on the couch after waiting for almost two hours. She went to the intercom and hit the button. "Who is it?"

"It's Fitz. I'm sure you're pissed. I'd be pissed. But I'd like a chance to explain myself."

Olivia frowned sleepily then looked at the clock in the kitchenette. She thought of turning him away out of spite, but something told her he hadn't just blown her off. She pressed the button to open the door then hit the intercom again. "Come on up."

A few minutes later there was a knock at her door and she opened it to find him standing before her in a navy suit. He gave an apologetic smile, a bouquet of red tulips in his hand. "Hi."

"Hi." She stepped back to let him in.

Fitz entered the apartment and looked around. "Nice place. Great view. How do you afford this?"

"We're illegally subletting from Quinn's brother. He moved to Scarsdale with his wife and let Quinn have the place. And she let me move in after my parents kicked me out."

He nodded as he sat on the couch. "None of your furniture matches. Is that a thing you kids are doing now?"

Olivia laughed as she sat in Quinn's overstuffed armchair. "You kids? Christ, how old are you? But to answer your question, I don't know if it's a thing. Quinn and I just really like flea market furniture."

Fitz nodded then looked at her with a frown. "I'm sorry about tonight. One of my accounting heads was arrested for investment fraud and the FBI turned my office inside out."

Olivia's eyebrows raised. "Investment fraud?"

"He does some private accounting on the side and he was shuffling their money in dummy accounts so he could live off it. They came to see if he was embezzling company too. He wasn't, but it was an all-day thing. I meant to call you back but…" He met her gaze. "I hope you'll let me ask you out again."

Olivia could only smile at his guilty expression. She stood. "It's not that late. We can still go out."

"It's almost eleven."

She smiled, wrinkling her nose. "You said that like it's almost sunrise. Just let me freshen up and I'll take you to the best restaurant in the city."

She picked up the remote from the coffee table and tossed it to him then went into her bedroom. Fitz turned on the television and began flipping channels. He looked up at the sound of footsteps and found Quinn sleepily schlepping to the kitchen. She got something from the refrigerator then came back into the living room and plopped on the chair where Olivia had been sitting. Fitz wasn't sure if he should speak to her as she hadn't spoken to him, instead glancing at her unsurely until she looked at him. Her eyes widened as she woke up completely. "Oh, hi. Didn't see you there."

"Hi," Fitz replied.

She smiled. "You're here late. I take it the date went well."

"We haven't been yet. I got caught up in some work stuff. Liv's just changing her clothes and then we're gonna go." As if he'd summoned her, Olivia appeared in the doorway, a flannel shirt open over her black dress and her pumps gone, replaced by her Birkenstocks. She had pulled her dark freshly re-twisted locs into a bun at the crown of her head. Fitz smirked. "I suppose I've earned those shoes."

"Shut up and come on." She smiled as she put her beaten leather purse on her shoulder. Fitz stood and said goodnight to Quinn then followed Olivia to the door. "You've been to Harlem before, right?"

Fitz shrugged. "I went to Spanish Harlem like a million years ago with this girl I was dating to meet her family. Her brother called me a gringo and told her she couldn't see me anymore."

Olivia laughed as she descended the stairs. "Hopefully this experience will be better."

"I'm not dressed like Sonny from Miami Vice, so it's already off to a better start."

Olivia squinted at him. "Miami Vice? How old were you?"

"It was 1986 so I was 20, maybe 21." He looked at her with a smile. "How old were you?"

"Eleven. Miami Vice came on after my bedtime."

Fitz blinked. "Eleven? You're 24?"

"Yeah…" Olivia wasn't sure what to make of his surprise. "Why?"

"I knew you were young but… I feel like such a dirty old man for liking you."

"How old are you?"

"Thirty-three."

She snorted a laugh. "I thought you were like 40. Chill."

Fitz laughed at her slang as they walked out into the cool evening. Fitz's driver, David, leaned against the car, smoking. "Dave, this is Olivia."

David smiled and nodded at her, taking a last drag off his cigarette before he dropped it and stubbed it out. "Nice to meet you."

Olivia smiled at him then turned to Fitz. "You have a driver?"

"Only on weekdays. On the weekends, I drive myself around in my Jeep. Of course, I'm usually upstate at my cabin."

David opened the back door for them and Olivia climbed in, smirking at Fitz as he followed. "You have a cabin upstate?"

"Well it's more of a country house than a cabin. There's a lake. It's cozy."

Olivia snickered. "You're ridiculous."

"So you've said," Fitz replied with a smile. "You should come up one weekend. It's great this time of year."

"I work on weekends."

"All of them?"

Olivia nodded. "Usually."

Fitz shrugged. "That's okay. Just tell me when you wanna go and I'll clear my schedule."

There was something about the earnest sweetness of his eyes that made Olivia's face warm. She looked away from him, desperate to distract herself from the growing urge to kiss him. "Mind if I bother your radio?"

Fitz nodded. "Go ahead."

She took off her seatbelt and leaned over the console to twist the dial. She stopped on a station then sat back beside him, a grin spreading over her face as the DJ on the pop station announced a throwback and an unmistakable beat began to play. "Oh my god! I haven't heard this in forever!"

Fitz smiled at her. "You're old enough to remember N.W.A?"

Olivia laughed and rolled her eyes. "I'm not that young! Plus 'Straight Outta Compton' is a classic."

Fitz watched with a surprised smile as she proceeded to rap the whole song. When she finished, she looked at him with a triumphant grin. "I was not expecting that."

"I'm full of surprises," she replied.

xxxxx

Giani's was a small dingy pizzeria tucked away in the middle of Harlem. Fitz frowned at the cluster of teenagers smoking beside the recessed front entrance as he followed Olivia inside. He looked around at the bare brick walls and groups of people sitting at the mismatched tables and chairs. Looking around, he was sure he was the oldest person in the place. Olivia smiled as she led him to the counter, speaking to people they passed.

She turned to him. "This is the best pizza in the city, and they've got jug wine."

"Jug wine?"

"Best in the city!" an old man in a sauce-spattered white apron announced as he walked to the counter.

Olivia laughed. "Fitz, this is Giani! He's like a thousand years old, but he can still toss a pizza like you wouldn't believe."

"Best in the city!" the man repeated.

"So what do you recommend?" Fitz asked.

"For you, pepperoni and sausage." He smiled at Olivia. "For her, though, extra cheese. I make half and half, yes?"

"Sounds good to me," Fitz replied. The old man scribbled the order on his pad then headed for the kitchen, calling the order out in Italian.

Fitz was surprised when Olivia took his hand to lead him to the bar. She bought them $1 beers despite his objections then led him to one of the pool tables near the back of the room. She looked back at him expectantly. "Teach me to play?"

"I'll see what I can do. I'm more of a darts man, myself." He showed her the basics before setting up a real game. "Alright. Now that you've got the hang of it, let's play a game."

"Wanna make it interesting?"

Fitz raised his eyebrows. "What do you have in mind?"

"Two dollars a ball?"

Fitz nodded. "You're on."

"Mind if I go first?" He handed her a cue then stepped back. Olivia lined up her cue then leaned over the table. Fitz completely missed her shot, his eyes far more concerned with the way she bent over the table, and only moved back to the game when she gave a delighted squeal. She grinned proudly. "You owe me six dollars!"

Fitz looked at the balls scattered on the table. "You sunk three balls at once. How?"

"Like this." She replicated her shot and sunk three more balls.

Fitz smirked at her as he pulled out his wallet. "I'm getting the strong feeling I'm being hustled."

Olivia smiled innocently, batting her eyelashes. "I would never do that, Mr. Grant. It's just beginner's luck."

Olivia's "beginner's luck" won her forty dollars. Fitz shook his head as he pulled out his wallet. "Alright hot shot, let's play my game."

They abandoned their pool table and went to the dart board where Fitz managed to win back ten dollars before their order was called. They took their pizza to a back booth and sat down. Olivia nodded at the small jukebox on the table. "These have the best music on them. It's all these great songs from the 70's. That was like the peak of good music."

Fitz dug a quarter from his pocket and popped it in the machine. He shook his head. "The peak of music was definitely the mid-80's."

Olivia shook her head too. "You weren't there. You don't know."

Fitz gave a scoffing laugh. "I was in middle school, and you spent the better part of that decade as a twinkle in your father's eye."

"Not the point. The music is the point." Olivia smirked as she began flipping through the songs. She squealed as she stopped on one. "Oh my god! This is the best song ever!"

She turned to him with a smile. "Have you seen The Way We Were?"

"Probably once with my ex-wife."

"Well this is the title song. It's from my favorite scene. I swear this is like the scene that made me want to be a screenwriter!" She smiled prattled excitedly. "It's after they split up and Katie runs into Hubbell on the street after she has their baby. And you can tell they haven't seen each other in a long time, but they spot each other and you just know the love is still there—like you know—and they make small talk for a bit about the baby. Then the camera pulls back and you see his new girl—the simple girl with the straight hair in the simple white dress—and she looks up at them curiously then gets into the car. And the camera cuts back to Hubbell and you can tell he's about to give Katie this long explanation, but she stops him. She pushes his hair back and smiles at him and says, 'Your girl is lovely Hubbell. And I miss the way we were.' Then the camera pans to the sky and the music starts. Memories/ Like the corners of my mind/ Misty watercolor memories/ Of the way we were…."

Fitz couldn't contain his grin as she sang along to the song. "You are so cute."

Olivia blushed, smiling at her hands as she took a slice of pizza. "I bet you say that to all the nerdy girls you date."

He continued smiling at the side of her face, the wispy curls bordering her thick black braids, pulled up in a bun, the heart tattooed behind her left ear, the rosy blush on her cheek. "Actually I don't. The girls who usually go out with me don't talk much."

"So you're into the mysterious, silent type?" Her smile was teasing as she turned to look at him.

Fitz smirked and shook his head. "No. Models are apparently devoid of general conversation."

"Models? Like runway models?" Olivia snorted. "You've fallen a long way if you're buying dates with diner waitresses."

His smirk became a smile.

"I disagree." He picked up his own slice of pizza but Olivia stopped him from biting it. She grabbed his chin and turned him to face her then kissed him, a soft sweet peck. Fitz smiled, his ears red. "I thought kisses came at the end of the night."

Olivia smiled back. "I disagree."

xxxxx

David pulled to a stop in front of Olivia's apartment building and Fitz got out, holding his hand out to help Olivia. He smiled at her as she stepped out of the car. "So how did I do?"

She smiled. "So much better than I thought you would."

He stuffed his hands in his pockets. "So you'll let me take you out again? On the originally intended date?"

Olivia nodded. "Because you did so well, I'll even wear different shoes."

"I don't mind them so much anymore." He looked down at her Birkenstocks then back at her face, grinning at her smile. "I just earned another kiss, didn't I?"

"And some cool points." She laughed as she stood on her toes to kiss him again.

A/N: Don't forget to review! XOXOXO