AN: This little piece of fluff has been nagging at me for days and I finally had to write it down. Sorry if there are any typos I don't have a beta at the moment.
I don't own Arrow but if I did the finale would have ended differently.
It was a chilly evening late November of 2006 on Thanksgiving break, when they first crossed paths. She was walking through her favorite park in Starling City. She was texting her friend Alice on her new Samsung camera flip phone, when she suddenly bumped into a stranger. She looked up and immediately realized who it was, Oliver Queen. While most girls her age would completely fall at their knees, apologizing all she did was mumble "Sorry" and gave a nod of acknowledgment. Little did she know that the man she bumped into that day would make such a huge impact on her years later six years to be exact.
It was a cold morning in late January 2007 the second time they crossed paths. This time in a coffee shop called Jittery Joe's in Boston near MIT although was often frequented by Harvard students as well. She was in line with Alice talking about their cyber terrorist class and the test coming up that Friday. Oblivious to her surroundings she suddenly heard Alice call her name just as she ran into what looked like a frat boy from Harvard. He turned around and before she could apologize, he turned around and smiled his playboy 100-watt smile, which very quickly turned into a puzzled look.
"Wait... Didn't you run into me in Starling City?" Queen asked perplexed. While she just stood there shocked what were the chances of seeing him again? In Boston no less.
"What are you doing in Boston?" she asked ignoring his question.
"Well Felicity, that is your name right, I heard your friend call it out before you walked into me." she nodded in confirmation. "I am a student at Harvard, and by your T-Shirt I can only assume you go to MIT."
"I do, go to MIT I mean." feeling her cheeks blush as she managed to keep her babbling to a minimum. "I apologize again for literally running into you twice. It hopefully won't happen again." she replied grabbing her latte.
When the barista made a comment on how both she and Oliver get the same latte whenever they come. She looked towards Oliver and saw him beam distracting her almost spilling her latte on her computer in her left hand.
"I'd be careful if I were you, I hear lattes are bad for laptops." and with that he turned and walked out the door.
It was four months later when she saw it on the news, "Oliver Queen Presumed Dead After Deadly Ship Wreck" and while she had only met him twice, she felt a pang of sadness for the man. About two years after that she dyed her mousey auburn hair a golden blonde and completely changed her wardrobe. She moved back to Starling City where her Grandmother, the only person in her family she still talked to, lived. She got a job at Queen Consolidated in the IT department and quickly became Walter Steele's favorite computer girl.
It was two and a half years later when they saw each other again. He walked through the door and saw her and he couldn't help but stare for a millisecond. "Felicity Smoak? Hi I'm Oliver Queen."
She turned seeing his face and looking a little awestruck as she took the pen out of her mouth. She wasn't stupid she heard the news and the gossip in the halls she just didn't expect him to walk in her office. But he did, which caused her to word vomit. "'Course I know who you are... you're Mr. Queen."
"Mr. Queen was my father." he watched her slightly amused she was more flustered than he remembered her being five years ago.
"Right... but he's dead...I mean he drowned...but you didn't which means you can come down to the IT Department and listen to me babble. Which will end in 3...2...1." she sighed slightly finishing her embarrassing ramble.
"I'm having some trouble with my computer and they told me that you were the person to come and see." he paused for a millisecond taking her in and thinking of an excuse to give her. "I was at my coffee shop surfing the web and I spilt a latte on it."
"Really?" she asked, keeping herself from laughing. A conversation from five years ago coming to mind, in a coffee shop in the middle of Boston.
Smiling he chuckled "Yeah." She couldn't help but notice that he seemed like he had a weight on his shoulders that wasn't there before. But what would she know it's not like she actually knew him.
"'Cause these look like bullet holes." She said as if she was talking to a first grader, slowly so he could understand her.
"My coffee shop is in a bad neighborhood." while she knew it was a blatant lie she decided to help him. It was the least she could do for always bumping into him. That was the beginning of their tumultuous friendship.
The last time she bumps in to him is a chilly day in late November, and she's wearing a white dress. A white dress she trips on, towards the end of the aisle, running straight into the groom. She grumbles lowly "Not again!"
"I wouldn't have it any other way." Oliver said kissing her forehead and waiting for the priest to start the ceremony.