A/N: This is a story I've been thinking about writing for some time. I'm going to try and update more often than I normally do but the chapters won't be as long. I hope you enjoy this particular version of Olivia and Fitz :)

Chapter One: Nothing to Lose

The November day was unusually warm and Olivia slowly slid her black sunglasses on. She was irritated at her friend who decided last minute to cancel their plans for lunch. She sat on the outside patio of the cafe and tossed her phone back into her purse. It was such gorgeous day outside she hated to leave. When the waiter finally approached she didn't hesitate when letting him know she would indeed be eating alone.

The nearby park was busy and Olivia couldn't help but people watch. She smiled at the two kids playing tag and became slightly jealous she didn't have the energy they did. Her phone chimed indicating she received and email when she saw him approaching. He was following her waiter and walking in her direction.

Butterflies filled her stomach and an unusual nervousness set in. He was looking right at her and at she suddenly had the urge to get her mirror out and check her make up.

Without thinking, she grabbed the menu from the table and opened it, pretending to actually read the inside. She knew the table next to her was empty. Her eyes strained to see if he had on a wedding ring and for a split second she considered leaving. This was so out of her character.

She slightly shook her head and decided to put the menu down. The gentleman was now seated nearby and faced her general direction. His presence was unnerving and for the life of her she couldn't understand why. Her throat felt dry and she decided to take a sip of water.

Her food arrived and she was thankful for the distraction. The waiter was attentive and Olivia appreciated his kindness. He was an older man and his eyes reminded her of her father. As soon as he left, she began to eat and tried her best to look in the opposite direction. She could feel his stare and desperately wanted to return it. There was something about him...

She overheard him order for two and her heart sank. Clearly, he was expecting company and she was acting like a love struck teenager for no reason. The waiter passed by and she stopped him, asking for the check. He nodded and disappeared leaving her alone again.

Olivia reached for her purse and shifted through the bottom looking for her wallet. She spotted the man out of the corner of her eye stand. He began to walk towards her and she quickly stopped the fidgeting. The closer he got, the more her anticipation grew. He was so attractive...too attractive...and everything inside her could not have been more drawn to him.

"I see that you're leaving...I had to ask...do I know you from somewhere?"

His blue eyes shot straight through her and she smiled shaking her head no to the question.

"I don't think so...are you from New York?" She cleared her throat before she spoke and took a quick glance at his hand. He wasn't wearing a wedding ring.

"No...I'm actually visiting my sister. She's on her way. You look so familiar..." He stood smiling and Olivia admired the view. He wore dark slacks with a dark button down. His hands shifted to inside his pockets and he he didn't seem to be in any hurry to get back to his seat.

"First time in the city?" She asked, pulling cash from her wallet.

"My second." A bit of awkwardness set in and Olivia stood trying to decide her next move. She saw his eyes wonder behind her and followed his gaze. Two young girls approached her carrying a Playbill in their hands.

"Ms. Pope! Can we please have your autograph? You were amazing last night!" She smiled and took the marker from their hands and quickly scribbled her name. When she turned back around she saw the mixture of amusement and embarrassment spread all over his face.

"Well that explains why you looked so familiar...you WERE great last night." His cheeks were slightly crimson and his boyish grin made her knees grow weak.

"You enjoy Broadway?" Surprise filled her tone and she watched him shift from side to side.

"I enjoyed you." His voice was deep and his words washed over her like a tidal wave. Her cheeks flushed and she silently thanked the Gods above for inventing the vibrator because she knew it would be used tonight.

Olivia Pope was used to getting compliments but this was different. He was different and although she wanted to stay and continue the flirting, her conscious kicked in and reminded her he was a complete stranger. She suddenly could hear her mothers voice in the back of her head telling her how the world was full of people who couldn't be trusted.

"Enjoy your lunch...it's a great day to eat outdoors." Olivia smiled and put some cash down on the table, deciding not to wait for the check. She began to walk past him when her purse bumped into a nearby chair, knocking it down. Before she had time to turn around, he was at her side bending down to help her.

His hair was mesmerizing and his back muscles filled every inch of his shirt. She quickly looked away, trying very hard not to stare. When he finally stood he was smiling and held on to her purse instead of returning it.

"That's not a good color on you," she said through a broken laugh.

"I bet every color looks good on you," he quickly replied. His smile shifted and Olivia was taken back by his confidence. They stared at one another for some time until he finally handed the purse back to her.

Olivia took her bag and turned on her heels, after thanking the gentleman. She weaved through the tables until she found the iron gate and turned its latch to exit. A breeze filled the air and she crossed her arms making her way back towards her car. She walked a few blocks and couldn't stop smiling at her previous encounter. There was something endearing about the gentlemen, not to mention the physical attraction.

When she finally arrived at her car she took her keys out and the black Audi parked behind her grabbed her attention. The license plate on the front read "III" and the windows were darkly tinted. Olivia loved Audi's and she admired its beauty for a short while before finally climbing inside.

Her cell chimed and she once again reached into her purse looking for her phone. A small card grazed her fingertips and she lifted it out, looking it over. The card wasn't there before and she wasn't certain how it even got there to begin with. Visions of the gentleman bent down in front of her resurfaced and her heart began to race inside her chest. Olivia turned the card over and read the following:

Fitzgerald T. Grant III

Grant Architecture Firm

816-555-9010

She stared at the rows of cars parked ahead deep in thought, wondering if the "III" on the license plate matched the one on the card. After a few minutes she decided to grab a pen and turn the card over jotting down her name and number. Adrenaline set in and took completely over. Without thinking further, she stepped out of her car and walked to the black beauty behind her. She slipped the card underneath the windshield wiper and smiled at herself returning back to the front seat. Maybe he would call...maybe he wouldn't.

Either way she felt as if she had nothing to lose.