He starts lying to her almost from the moment they meet. At the time, it's a means to an end, but he eventually comes to feel bad about it.
She's sitting behind her desk chewing on a red pen as she works. The first thing that strikes him is how young she is. When the older, rumpled IT Director told him a Felicity Smoak was their best, he didn't really know what he expected. Definitely not a fresh-faced blonde in a pencil skirt and a pink blouse.
Like every other woman he encounters, she's a little flustered when she first sees him and he's so used to it now that it's more boring than flattering. Except then she embarks on the most awkward ramble he's ever encountered and it's suddenly fun again. One second he's introducing himself and the next she's bringing up his dead father and literally counting backwards aloud to stop herself. She presses her lips together as if her mouth might betray her again and he spends a moment pondering the fact that while the magenta shade painted on them initially seemed a little off, it actually manages to accentuate her mouth amongst all the other striking features: the blonde hair and the blue eyes and the black, rectangular glasses. But then he doesn't know why he's thinking about her lips at all, so he gives her an amused smile and hands her the laptop.
He had a better explanation for the bullet holes planned out in his head, but when it comes time, he says some lame line about spilling a latte on it. Maybe part of him wants to see how she'll react; he's so used to lying to everyone at this point that he wonders what it would be like for someone to catch him. He nearly laughs at the look she gives him: like a schoolteacher dealing with a student who just struck another and then immediately denied it. Her pursed lips conveying the "are you kidding me?" they don't speak. Yes, the magenta is a good choice. He soldiers on, committing to the lie and she eventually seems to accept it as part of the Oliver Queen legend and sets to work.
He pulls up a chair behind her as her hands fly over the keys at lightning speed. She's clearly adept and it's not just the fact that the chair he's sitting in places him slightly lower than her that makes Oliver feel a little like a student again. Her desk is organized, efficient and conspicuously devoid of personal touches. He wonders if this is intentional or an indication that she doesn't have much of a life outside the walls of Queen Consolidated. He'll have to check up on her background later—at least to see how old she actually is, which judging by sight could be as little as 19.
Finally, she gets past the encryptions and passwords and Oliver asks her to open a file marked with today's date, clearly whatever job Deadshot came to Starling City to perform. They're blueprints for a building where some auction is supposed to take place and Oliver only feels more like a student as Felicity (sounding downright annoyed now that the laptop is clearly not his) drops a Shakespeare reference while telling him that Floyd Lawton is working for a competitor. Suddenly, this whole situation looks a little like corporate espionage and she gives him a suspicious look before turning back to the computer to disconnect it. This could be a problem, Oliver thinks to himself. He'll definitely have to check up on her.
Felicity Megan Smoak ends up being slightly older than he expected, but hasn't been legally allowed to drink for enough time to make him totally comfortable.
The next time they talk, she's not so pleased to see him, saying something sarcastic about adding Oliver Queen's "Personal Internet Researcher" to her job title before he gives her a look that reminds her that he's also her boss. She backs off and he feels a little more in control, especially since he took the time to think up a better lie. This time he's just trying to find an old pre-island friend. Sounds innocuous enough, but once again, she destroys it within minutes.
Turns out, Derek Reston is a former employee of Queen Consolidated who got screwed over when the steel factory shut down. So, in some small way, this business, his business, shares some of the guilt for the Reston family's crime spree. He doesn't like getting reminders that his father contributed to the city's corruption. Yet somehow the way Felicity describes it, like a smug accusation–first for not knowing Reston at all and second for not knowing the horrible things that allow him to keep acting like a self-obsessed playboy–makes him feel the most shame. As if disappointing some nobody tech girl matters. But it does matter that it happens in front of Diggle and that he probably shares her low opinion.
Maybe that's why he considers offering Reston a new job at all and he feels a little better after, even if Reston doesn't take it.
Oliver decides that if he's going to keep using Felicity as his personal tech wiz, he'll have to make some changes. He puts in a request to have her desk moved somewhere a little more secluded, somewhere he can sneak into without being noticed. It's easy to hide as part of her recent promotion. They're too easily overheard in her old cubicle and he can't order her up to his office all the time. The more people see them together, the more they're going to wonder why. Not that Oliver necessarily minds the implication (he's got an image to maintain), but he doubts Felicity worked so hard to graduate a semester early from Starling State just so all of her success could be misconstrued as the result of some overtime with the company's womanizing heir.
He walks into the dark, intimate space for the first time and finds her staring at her tablet. As she did the first time they met, she doesn't notice he's there. He stares at her for a few seconds, her petite frame backlit by the blinking wall of servers behind her. The pink lipstick is a bit softer this time, but it contrasts so much with her light blue shirt that her lips are still what draw his eyes.
"Hey?" he asks and he almost bursts out laughing when she nearly jumps out of her seat.
"Don't you knock?" she says a little defensive and clutches the tablet a little tighter.
"Felicity, this is the IT Department," he says smiling and pauses for a second to wonder if her reaction might suggest she was looking at something not entirely work appropriate, "not the ladies' room." She lets out a short laugh as she sets down the tablet and he's a little surprised by the sound. Usually she's the amusing one. He wonders what it sounds like when she really laughs.
They get down to business then. He's come fully prepared with a story about a friend named Steve with a penchant for archery. She immediately makes a crack about how she thinks it looks "utterly ridiculous" and Oliver has to struggle not to share his opinions on the matter. This lie manages to last longer than the others and she gets a little huffy when it finally breaks down, but continues to play along anyway. He supposes that's just their routine now. As always, she easily finds out where the shipment was sent and writes it on a slip of paper in a unique almost whimsical script.
"Felicity," Oliver says, grinning at how she uncovers information as easily as he asks for it, "you're remarkable."
"Thank you for remarking on it," she responds. There's clearly satisfaction in her voice, but Oliver's surprised to realize there's a hint of flirtation that makes her voice sort of low and suggestive. It's an even nicer sound than the laughter.
He stands and wishes her a Merry Christmas as he turns to leave, but she quickly interjects that she's Jewish. Turning around, a little disappointed that that means he can't invite her to the big Queen Family Christmas party he's planning, he wishes her a Happy Hanukkah instead. She smiles and as he leaves, he wonders if it's still apropos to give her a gift.
It's well after business hours when he goes to her office to see if she can break into the security fob of some armored car thieves, so he doesn't really expect her to be there. Yet there she is, digging into a box of Chinese take out. He wonders if she eats many dinners like that, not just in her office, but at home as well. Seems a shame really, she's probably a fun date.
She quickly sets down her food and starts rearranging her desk when she sees him, looking just a little excited to break down another of his clearly fabricated stories.
"And here I was beginning to think my days of being Oliver Queen's personal computer geek were coming to an end," she says playfully.
"Is that your way of saying you missed me?" he teases.
"No, but if it works for you, go with it," she teases back. Oliver chuckles, a little glad that someone foolishly failed to ask her out tonight.
This time he's really thought about his story, though he supposes he's cheating a bit since he actually did organize a similar scavenger hunt shortly before ending up on the island. The only difference being that the prize at the end was a case of Lafite Rothschild 1988, not '82.
"Ooh," she coos when he names the vintage, "I love red wine." If only he'd known that during the holidays.
As always, she's bringing down the fob's military-grade security protocols within minutes and his lie is going with it.
"The idle rich are hard to entertain," he hedges, but he knows it's only a matter of time, so he decides to at least make it out of the room before the lie crumbles. "Listen, you get through it and one of those bottles of wine is yours," he says sweetly and gives her a playful tap on the shoulder. She smiles and looks up at him through her eyelashes as he walks out of the room and for a second, Oliver wishes his lies had longer shelf lives.
Though he's glad he's not there when Felicity realizes what she's got ahold of and suggests they call the cops. His slightly panicked lying probably isn't very convincing and he's thankful she can't see his face. He feels bad about being curt, but maybe he'll make it up to her by getting her a bottle of the Rothschild anyway, surely there's one in the Queen cellar.
He doesn't judge himself too harshly next time; he is under the influence of Vertigo, after all. Standing seems a better use of energy than coming up with a lie she'll just destroy anyway. Though he doesn't realize just how seriously the drug is affecting him until she goes on one of her rambles and he's too distracted by the light streaming through the window behind her to find it charming. He does pay attention when she gets a little feisty, however.
"Sounds like you need a Bloody Mary and a pretzel—not the IT Department," she says not entirely unkindly when he excuses his appearance on a hangover.
"Actually, my buddy Kevin is starting an energy drink company. He says it's fantastic for curing hangovers, but I am very particular about what it is I put in my body..."
"I've noticed," she interrupts and the way she says it, low and evocative, as she runs her eyes up and down his form, has a distinctly personal flavor. Like she thinks of him as more than just the arrogant billionaire who comes to lie to her every once in a while. Her body tenses immediately and she shuts her eyes, mortified. "I said 'not noticed,' right?" She looks to Diggle for assurance, but gets none. Oliver tries to continue his lie (he really does fear the drug will do permanent damage even if he won't admit that to Diggle), but he can't get past her slip because it only gets more amusing the more he thinks about it.
He eventually does and once he hands her the Vertigo, she seems recovered, looking mortified on Oliver's behalf when the only excuse he can come up as to why the alleged energy drink is in a syringe is that he "ran out of sports bottles." Diggle is kind enough to make a beeline for the elevator at that one and Felicity gives him her usual disappointed teacher look before leaving as well.
"Your BS stories are getting worse," Diggle chides when Oliver steps into the elevator.
"Well aware," he responds. Lying to get Felicity to dig up information is growing tiresome and it's not the first time he's thought it would be much easier if she were in the loop too. But she's not like them. She's never had to come to terms with violence to stay alive like they have. She's just some IT girl who's lived her whole life in Starling City and grew up with eccentric, if normal parents who teach at a local high school. He can't put her in danger just because it would facilitate his illegal activities. Still, it would be nice not to see that annoyed, disappointed look on her face every time he needed a little information.
And he realizes later that maybe he's underestimating her. When she asks him to meet her at Big Belly Burger that night, she's clearly nervous when she arrives. He tries to make her comfortable by brushing off her question about whether she can trust him and then apologizes when he sees that she's serious and doesn't find playboy Oliver cute right now. He doesn't know what he expects her to say, but he certainly never imagined she would pull a less battered copy of his father's notebook from her purse, the sinister item looking so out of place in her small, feminine hands.
All the playfulness is suddenly gone from the conversation and he's struggling to make sure she doesn't see how upset the notebook makes him. Clearly he fails, though, judging by the surprised and concerned way she asks if he's ever seen it before. He can't bring himself to look at her when he denies it because she's too good at knowing when he's lying. Finally, he feels composed enough, but the look on her face–probing and worried–and the way his voice shakes when he asks where she got it aren't as convincing as he needs them to be. But he's sure that's nothing compared to his reaction when she says that Walter suspected the notebook belonged to Moira Queen. He feels the Hood replacing the affable, vapid Oliver Queen as that news sinks in and the edge of fear that creeps into the intense interest in Felicity's eyes tells him it's written all over his features. He has to get out of here, has to get away from Felicity's piercing intellect and try to come to terms with the horrible sense of betrayal that's clouding his mind.
"Thank you for bringing this to me," he says softly and stands.
"Sure," Felicity says and takes a step back. Her lips are parted like she wants to ask more questions, but doesn't know which one to ask first. She places a hand on Oliver's forearm and starts with, "Are you going to be ok, Mr. Queen?"
"Yes, and please call me Oliver," he says with a genuine smile. "Are you going to be ok getting home?" he asks, suddenly noticing how deserted the streets are because of the rain.
"Oh, I just live a few blocks away," Felicity replies, "plus I have to wait for my food." She gestures at the counter and smiles. "I'll just bash any attackers with my Deluxe Big Belly and fries and that should knock them out cold. That's pretty much how I feel after I eat it."
"Ok," he says and chuckles just a little. He steps around her, nearly sprinting out of the restaurant toward his car and when he slams his door shut, his breath is labored more from rage than the movement. His mind is racing too fast for him to do anything but grip the steering wheel so hard that his knuckles start to ache. The sight of Felicity leaving the restaurant is what finally snaps him out of it. She's swinging a bag of food bigger than her head at her side and whistling a melody Oliver doesn't know as she walks down the street. She looks as if she's strolling through a field of daisies instead of down the dreary streets of Starling City and it makes her look just a little too vulnerable. So he decides to follow her, just in case.
After a few blocks, she climbs the stoop of a small, older looking building and he parks on the opposite corner to watch as she presses the call button and waits as somebody buzzes her in. Odd, Oliver was sure she lived alone; at least, Felicity Smoak was the only name on the lease for apartment 4C when he checked. Though now it seems silly that he assumed that huge bag of food was all for her considering she's about a third his size. Maybe she's got a subletter or has a friend over, maybe even a boyfriend. If it's the latter, Oliver isn't sure the guy's worth her time if he let her pick up and pay for the food while he sat on the couch watching TV. He's just thinking that maybe he should climb the fire escape to get a look at this jackass when the sound of his car door opening surprises him. When did he even take his hands off the wheel? He shakes his head a little and reminds himself that who Felicity shares dinner with is none of his business; he's got a bigger problem in the form of a tiny notebook.
Nothing should really surprise Oliver anymore. The last five years of his life have been filled with one improbable event after another. Still, dying from a gunshot inflicted by his own mother seemed more than improbable, more like impossible. Yet here he is, quickly bleeding out as he scales down the side of Queen Consolidated.
He finally hits the ground just outside the entrance to the building's underground parking lot and immediately stumbles onto the concrete. No way could he building hop back to his father's abandoned factory in this state. He could try stealing a vehicle, but at this rate, he'll end up passing out from blood loss and crashing it before he gets too far. Calling Diggle won't work either; he'll probably slip into a coma before his partner can drive all the way over and get him back to the factory. The sound of police sirens reminds him that he's a little conspicuous laying in the middle of the sidewalk dressed as the Hood, so he painstakingly pushes himself off the ground and stumbles toward the garage, leaning on the wall just inside when his vision starts blurring.
At least it's late enough that nobody is likely to find him down here. There are only a few cars left, including a little red Mini Cooper he's pretty sure belongs to one Felicity Smoak. Well, there's an option, he thinks—he could break into her car. Worst case scenario, he has somewhere to hide from the cops and can bleed out peacefully. Best case scenario, she finds him back there and drives him to Diggle. He checks his watch and reads 6:53. She'll be off work any minute so he has to decide now if he can trust her.
The question it really comes down to is whether she'll turn him in. It's the same thing he asked himself before he told Diggle his secret. That was probably a much bigger risk, really. He'd been antagonizing him for weeks and Diggle definitely didn't trust him then. He's at least already got that from Felicity. And she's seen a hell of a lot more suspicious activity from him than Diggle did. Plus, she's too smart not to figure it out eventually. Showing up in the back seat of her car will just make all the links she's probably already intuited. He doesn't want to potentially put her in danger, but it doesn't seem like he has another option.
He gathers his strength and pushes off the wall toward her car, using the last of his energy to disable the alarm and pick the lock on the door before flopping down on the back seat. Staying conscious is getting more difficult by the minute, but thankfully, it's not long before he hears the sound of heels echoing around the structure. She climbs in without noticing him and once she shuts the door, he makes himself known. Her reaction would make him laugh under different circumstances.
"I'm not gonna hurt you Felicity," he manages to pant out through the pain.
"How do you know my name?" she asks, a little scared.
"Because you know my name," he responds and removes his hood. Recognition and surprise wash over her face.
"Mr...Oliver. Oh, wow, everything about you just became so unbelievably clear." At least his lying was good enough to hide that, he thinks. "You're bleeding," she adds, seemingly having gathered her thoughts and realized the gravity of the situation.
"I don't need to be told that," he says
"You need a hospital," she counters and turns to drive.
"Wait," he chokes out, "my father's old factory in the Glades."
"No, you need a doctor, not a steel worker," she argues.
"Felicity, you have to promise me that you are gonna take me to my father's factory and nowhere else."
"Yeah, promise," she says and Oliver has complete trust that she's not lying. He lays back down on the seat as she starts the car. "Something tells me blood stains are not covered under my lease," she says as she backs out of the parking spot.
"I'll pay you back," Oliver replies.
"Don't think I won't hold you to that just because you're mortally wounded," she says over her shoulder as she pulls into traffic. "Where exactly is this place anyway?"
"400 Grand Avenue at 33rd St. Pull around the back." They continue to drive, but Oliver has no idea how long as he slips closer and closer to unconsciousness. The street lights flashing overhead and the sound of Felicity's anxious voice as she curses at other drivers are the only things keeping him awake.
Finally, the car comes to a stop and Felicity flies out of her seat and quickly wrenches open his door. He manages to pull himself into a sitting position, but he's too weak to stand. Without hesitating, she drapes his arm around her shoulders and tries to help lift him into a standing position, but he's too heavy and all they manage to do is get his blood all over the front of her shirt.
"Wow, I need to work out more," she says under her breath after she sets him down against the seat of the car. He reaches into his pocket and hands her a set of keys.
"The big silver one opens that door," he says with a half-hearted point. "There's a door with a keypad hidden in a short corridor about ten feet down the hall. The code is 141. My bodyguard Diggle should be waiting down there, he'll know what to do."
"Ok," she says and sprints to the door. After a few moments of fumbling with the keys and a few choice words, she gets the door open and yells, "I'll be right back, don't die!" before disappearing down the hall.
"Ok," Oliver calls out and then chuckles to himself. His last thought before his vision goes dark is that he hopes he's not lying to her again.