1.
While Oliver had learned many lessons over the past five years, one of the most important ones was how important it was to know as much about all the players as possible, whether they be friend or foe. Which was why he now found himself perched outside the window of one Felicity Meghan Smoak.
When he asked Walter earlier if he knew any I.T. experts the girls name had come across Walter's lips quick and easy. Smart and trustworthy was how Walter has described her, a fond look in his eyes. And while Oliver wanted to trust his step-fathers's judgment, he knew he needed to run his own background check on the woman. When nothing suspicious had popped up on the computer, Oliver had used the newly found information to sneak in while he knew she was at work.
Since he had never met the woman in question before, he wasn't sure what to expect from her home. It was nice and tidy, everything organized in such a way that reminded Oliver of the guest bedrooms in his own house. Her bedroom was a little more personalized with pops of color throughout.
If the computer search had barely brought anything up, the search of her apartment had surfaced even less. There was an obvious lack of personal effects in the apartment, only a couple pictures on the computer desk that let him know he was indeed in the correct place.
Probably the most telling part of the place was her closet. Her wardrobe was colorful and full of skirts and dresses, while her shoe collection took the entire space of one wall. Thea would be proud.
But really, Oliver decided, how dangerous could someone be when they wore Panda Flats and Robot Pajamas? Which was why, the next day, he found himself in the IT department, fake smile plastered on as he greeted her, "Felicity Smoak? Hi, I'm Oliver Queen."
2.
The night after his world is thrown off-kilter for the nth time, Oliver finds himself once again outside the window to Felicity Smoak's home. Only, this time she's actually inside of it. Sleeping restlessly in her bed, but there none the less. In his hands is the small notebook. The same book that just that afternoon, Felicity had produced its twin. The same book that had been his guiding light since returning from the island. A light that seemed more and more like a moth-trap every day.
He stays there, still as a statue, for a brief while longer before finally making his way through the window (left both unlocked and cracked open and it was honestly a wonder she'd made it this long in this dangerous a city) to complete his late night errand.
Once inside, he steps his way over to her night stand where her glasses lay discarded on top of her tablet. Oliver has snuck past more vigilant and dangerous people than Ms. Smoak, so it's no surprise when she didn't even stir in the slightest. He's learned to embrace the night - stillness, darkness, and stealth.
The glasses are light in his left hand while the small tracker is even lighter in his right. It's a tiny, circular piece no bigger than a screw head and built for the express purpose of tracking others without their knowledge. In this case he'll use it to keep an eye on Felicity. For her own safety, of course.
3.
Oliver hasn't slept well since before the island. His nights were spent pacing the floors instead of twisting sheets. And some nights, when it's worse than others and the sky is dark but there are no stars because the city's too contaminated and messy, Oliver suits back up in the green hood as the bow and just goes out. Tonight was one of those nights.
The urban landscape of Starling City is far different from the green forests of the island or the closeness of Hong Kong. And it has dangers of its own as well. Which is something he's learned thoroughly after tonight.
Count Vertigo. With his drugs and bad penny habits. Only this time, Oliver reminds himself, he won't be coming back. Vertigo would be no more. Because he killed him - shot him thrice and sent him flying out a window. Traded one man's life for another's. For her's.
Felicity. Who's window he was currently positioned outside of. It wasn't that much of a shocker. His nightly patrols usually ended up passing her apartment at some point. He needed to make sure she was safe - this night more so than any.
So, he crept around to her bedroom window, intending on only peeking in for a second - long enough to determine that she was safe. Only, she wasn't in her bed or in her room.
Oliver didn't think before sliding her (unlocked) window open and sliding in to her room, silent as the night. He went straight through and into the main hallway where he could hear soft noises.
And there, he found her passed out on the couch - empty tub of mint chip and worn fleece blanket and, most importantly, safe.
4.
He knew Diggle was keeping an eye on her and would do anything to keep her safe. If there was one person, other than himself, he could trust to keep Felicity safe, it was John Diggle.
He was also well aware of the fact that going and seeing her himself would do nothing but put her in more danger. Slade Wilson was a smart man who knew how to find his enemies weaknesses. And the more he revealed his connection to Felicity, the closer Slade would be realized just how important the blonde was to him.
But, Oliver had always been a selfish man. And right now what he wanted more than anything was to go to Felicity. To let her smile at him and hold onto him arm like she's the only thing anchoring him down in the storm that had become his life.
So somehow he'd managed to make his way across the rooftops and to her apartment. Her bedroom was dark and empty, but he could hear her and the tv further into the apartment. She was watching an action movie - as if her daily life didn't have enough shoot outs in it.
Oliver slid in through the window, only taking a moment to pick the lock. As quiet as the night, like he'd done multiple times before, he snuck across the bedroom and out into the hallway. He stuck to the shadows and was able to see where she was curled up on the couch, take out in front of her. He had no doubt that she'd ordered enough for herself and John. And probably for leftovers the next day - that girl was forever eating leftovers.
He leaned against the wall and the sudden displacement of weight caused a loud creak to sound. From her apt in the couch, Felicity straightened up and looked over to where he stood.
"Hello?" She asked, eyes scanning. The hallway he stood in was too dark for her to see anything properly.
As she stood up, he slowly made his way back down the hall and out her window - sliding it closed and taking off into the night.
5.
Oliver knew Felicity was expecting him so there was really no reason not to use the front door. Except, he hadn't really used it before and old habits tended to die hard. So, it was the window for him once again.
She'd asked once a week for months now but he usually shrugged it off and made some excuse. He didn't quite know what possessed him to accept her invitation of some tv and take out. (Except he totally did know - he was tired of being alone all night. With no place to go but the foundry, he'd become quite the hermit and it wasn't until Roy had made a joke earlier that day that Oliver had even realized it.)
"Something wrong with the front door?" Felicity asked, arms crossed as she stood by her bedroom door in green plaid pajamas.
That was when Oliver realized that almost every time he'd come in through the window, Felicity had been totally unaware of it. This time however, she was very much aware of him sliding in the tiny bedroom window as easily as if he was getting in and out of an Aston Martin.
"Is this how you usually get into a girls home?" She asked, a smile playing on her face, "By sneaking in the window?"
"Only yours."
6.
Oliver had spent a lot of time waiting - waiting 5 years to finally come home, waiting for the right moment to strike down an enemy; and, he considered himself pretty good at the act of waiting. At the current moment; however, he didn't think he was particularly patient or good at waiting. Because right now - standing outside of Felicity's front door for the first time while he waited to take her on their second (and hopefully less explosive) date, Oliver wanted nothing more than to just break down the door himself (or sneak in the window as had been his MO the last few times.)
But before he could do either of those things, Felicity was there opening the front door and greeting him with a smile and a babbled hello. She looked stunning in a black cutout dress, hair curled and lips red.
"Nice to see you used the door this time," Felicity said, "I was half worried I should get dressed the bathroom. Less chance of you seeing me naked in there. Not that I walk around naked or anything. Just, you know, I was getting into this dress that totally doesn't allow for a bra. Not that you needed to know that either. And I'm just gonna stop talking now."
"Felicity," Oliver chuckled, "It's fine. I thought the front door might be a more normal place."
"Well, we're not exactly normal, Oliver. I mean, we are doing this all sorts of out of order. We are going on our second date tonight and yet I've already seen you half naked and you've already met my parents and we know more about one another than normal second daters would. And I think I'm just going to invite you in before I babble the night away."
"That would be a good start," Oliver admitted.
"Yeah, a good start," Felicity repeated before holding the door in wider, "Oliver, would you like to come in?"
"I'd love to," Oliver answered and stepped across the entranceway and into the warmth.