A/N: Hi everyone! This chapter was starting to get away from me so I'll be cutting it in two. so consider this part 1 and I'll have part two up before the weekend is out.

Disclaimer: Nothing is mine.

Felicity's proactive genius had led to a break in the Deadshot case. Diggle was going to contact his old friend Lyla to figure out the details but it looks like they might have a chance. While they were wrapping up the discussion a look of sudden recollection passed Oliver's face.

"I have to have lunch with Laurel." Both teammates looked at him in surprise. Felicity felt her internal panic button go off, but was trying her hardest to stay calm and unconcerned on the outside. Dig on the other hand wasn't letting this slide that easy.

"Since when did you become lunch dates with Laurel?" He leaned on the desk and shot a disapproving look. He caught Oliver's eyes over her head and flicked his gaze down to Felicity to make his point.
"Look ,we're just ,friends." Oliver looked at Felicity to make sure she was ok with this.
"Friends are good." She said quietly, looking to Diggle for back up. He nodded and Oliver stepped away.
"But couldn't you be friends with someone less complicated that your ex girlfriend who is your ex best friend's current girlfriend?" She realized she was being completely insecure but she couldn't stop herself from asking. She knew he was annoyed by the way he strode off, barely looking at her while commenting about grading complexity on a curve.

She was replaying the exchange in her head as she unlocked the door and entered her apartment. She dropped her bag and pulled her hair out of its trademark ponytail before heading to the kitchen. She went to the fridge and pulled out an open bottle of wine. She really wished Robin wasn't on her honeymoon right now. This was the kind of mental aerobics that require your best friend not to be on a beach in Spain. She poured a large glass of white wine and leaned against the counter. Two sips in her phone buzzed. She glanced down to see Oliver's name on the caller id. After a moment's debate the possibility that it could be hood related outweighed her panic that it might be about something more personal. "Hi" she answered politely.

"Felicity, Hi." Oliver sounded nervous. "Um, are you busy? Are you home?"
"No and yes. Is something wrong?"
"No, just, I'm outside and I'm getting cold. I was wondering if I could come in for a bit?" There was a long pause while she processed that Oliver was asking to come up, to her apartment, to see her. "Felicity?"

"Yeah, sure! Just go find the buzzer and I'll let you up. See you soon I guess." She put down the wine and ran around the apartment doing a quick dirty laundry and lady things check. Having Oliver over for the first time was going to be stressful enough without him stepping on a pair of her undies. The buzzer startled her and she quickly made her way to the call box letting him up. She opened the door to see him standing there in jeans, a sweater and leather jacket with his motorcycle helmet under one arm. "Hi"

"Hi" He smiled reassuringly. "I was out riding and just kind of ended up here. Is that ok?" Felicity realized he was still standing in the hallway and moved aside so he could enter the apartment. Her apartment was modest but comfy. The couches were overstuffed grey corduroy with white throw pillows arranged for practical use instead of for style. The walls were a pale purple with a few framed photos and movie posters between massive bookshelves that held hundreds of books and DVDs.

"Quite a collection." Oliver commented. He placed his helmet gently on the floor as he took his first looks around the home. It was neat, smart and a little bit quirky, just like its owner.

"I like my stuff." She shrugged "You buy cars, I buy boxed sets. I was just having wine would you like some? Or something else?"

"Wine would be good, means you can't kick me out right away."

"No promises, depends what you have to say." She retorted. He raised an eyebrow as she headed to the kitchen to pour a second glass. "When you said you were outside and cold a part of me wondered if you were in Hood gear."

"I don't think I would have used the front door if that was the case." He took off his jacket and sat on the sofa. He grabbed a copy of Wired from the coffee table and flipped a few pages.

"Right, good point. I guess if you had to share an elevator up with someone that would be a little awkward to do. Wow you look good on my couch!" Felicity had walked back into the room and immediately her brain shut down letting that last little gem fall out of her mouth. Oliver looked up from the magazine bemused.

"Is that a line?"

"I don't know. I've never really had the chance to use one in here. Not that I use pick up lines on guys other places. Or even talk to many other guys other than you and Diggle and the IT guys. But I definitely never use lines, here, in my apartment, with guys." She made her way over and passed him the glass before sitting and taking a massive swig out of hers.

"Glad to hear it, more for me." He took a sip of wine. "I'm sorry about earlier. I shouldn't have spoken to you like that."

"I'm sorry too. You can have lunch with as many awkward ex girlfriends as you want. We aren't- well not yet at least, even if we were, I shouldn't be trying to tell you who your friends are. I blame Diggle." Oliver laughed

"Good, let's go with that." An awkward silence fell between them "Laurel is a part of my past. Currently she's the only part my past that is still speaking to me. I don't want to lose that link."

"I understand, I guess that's what having happy teen years does to a person." Oliver looked at her surprised. "Oliver, I was a flat, short, non-blond girl who played with computers. What part of that screams 'High school was awesome'?" He scooted closer to her on the couch, reached his hand and cupped the side of her face.

"Felicity Smoak, if they could see you now." He smiled and leaned in for a kiss. Eventually they paused just long enough to put on a movie and get some more wine. It was hard to guess whose high school self would have been more surprised at how the future had unfolded: The techie for falling for the playboy, or the playboy for falling for the techie.