Chapter Text
Oliver thinks that if he has to shake one more kiss-ass, fake smiling executive’s hand, he’s going to throw himself through one of the floor to ceiling windows that make up the penthouse offices. His mother pinches his arm at his side, noticing the sour expression most likely beginning to form on his face as the woman in front of him continues speaking.
It’s not his fault. He’s always hated the Bowens.
He pastes on a smile and nods genially, pretending to listen to his high school rival’s mom prattle on about this book deal and that medical degree. He’s used to the kind of conversation she’s making – smarmy one-upmanship. It’s exhausting. And he feels like he’s been at it for hours.
The Bowens move on and he sneaks a look at the watch on his wrist. In reality, they’ve only been making pleasantries for a little over an hour. His mother squeezes his arm gently, pulling his attention. He offers a sheepish look, feeling caught looking down at his watch, counting the minutes until all these people leave.
“It’s alright,” she sighs, tilting her head towards the long banquet table setup with refreshments, a bar at the end of it. “Take a break, get a drink.”
He nods, leaving her with a kiss on the cheek to cross the room. Oliver bypasses the hors d’oeuvres and small desserts to head straight for the bar. He orders a short tumbler of whiskey and secludes himself into a corner. He can see one of the executive’s young assistants eying him hungrily from across the room and maybe, if it were a year ago, he would have jumped at the opportunity.
Instead, he turns away from the party at large, looking through the glass walls that face out towards the elevator bay. The door to the staircase next to them swings open suddenly and a short blonde rushes into the atrium. She halts at the sight of all the people, easing the door shut quietly behind her. Oliver watches her curiously, startled at her appearance and the lack of adherence to dress code for the party.
When she moves slowly along the wall, keeping an eye on the party in case someone should notice her but completely oblivious to his gaze, only to sneak through the door on the other side labeled ‘roof access’. And then his mild interest turns to concern.
Setting his drink back down on the bar, he gives a cursory look around the room and then slips out the doors closest to him into the atrium where the woman had appeared. He slips through the roof access door just in time to hear the second door, situated up another flight of stairs, slam closed behind the woman. He follows her ascent, pushing the door open into the cold winter air.
She’s standing in the middle of the roof, the wind making the ponytail at the back of her head sway wildly. Her hands are shoved into the pockets of her coat, but he notices a camera dangling from her wrist. It also moves with the wind, but less due to its weight.
“Hey,” he shouts over the wind, halfway on the roof. He holds the door ajar, knowing that if it swings shut they both could end up stranded up here.
The woman, already looking frozen in place, goes somehow more rigid at the sound of his voice. She spins, the soles of her short heels kicking up the gravel that covers the roof and sending it scattering around her feet.
“You know this door locks automatically, right?” He calls, tilting his head at her. “And I don’t really think that just anyone is supposed to be up here.”
She looks caught, glancing back at the lip of the roof over her shoulder. He wonders what she’d come up here for and, worse, if she might make a break for the edge while he watches. Oliver decides not to wait for her to decide. He scoops up a sturdy enough rock – left next to the door, most likely by someone on one of the higher levels who uses this spot for smoke breaks – and sets it between the door and the frame, keeping it from locking them on the roof when he releases it. He crosses towards her and her hands pull from her pockets, tangling together anxiously in front of her instead.
“Sorry,” she says suddenly, spurred into action by him advancing on her. “I, uh, I didn’t think anybody would notice if I snuck up here for a minute.”
“I noticed,” he offers, a little obviously. “And you’re lucky I did or you might have been stuck up here.”
“I’d have found my way down,” she says stubbornly. But the words only unsettle him further. Does he want to know what her idea of a way down is?
“Like I said,” he repeats. “I don’t think anyone is supposed to be up here.”
“I know,” she admits, biting down on her lip and offering him a sheepish shrug. “But I figured security wouldn’t be as tight with the party going on, you know? So, I thought it was my best chance at going undetected. Clearly, I was wrong.”
Now that he’s standing just a couple feet from her, Oliver is realizing she’s beautiful. Her eyes flash with the lights of the surrounding skyscrapers, the bright light pouring from around them lighting the roof enough for him to make out the blue of them. Her cheeks are flushed pink from the cold.
“What are you doing up here anyway?” He asks, frowning at her.
“It’s kind of a long story,” she hedges and, honestly, Oliver isn’t even sure he wants to press. He just wants to make sure that his father’s company doesn’t make headlines tomorrow because this girl took a swan dive off the roof. It’d be a long way down.
Before he can make up his mind, though, she’s launching into an explanation,
“I’m terrified of heights. Like, panicky, shaking, throwing up kind of terrified. So, you know, I thought the best way to conquer a fear is just to immerse yourself in it and, go big or go home right? I mean, this building is huge , plus I already had access so-”
“How?” He asks, cutting her off. She seems startled by the interruption, confused. “How did you have access?”
“I, uh,” she starts, suddenly avoiding his gaze. “I work here.”
“So, you’re afraid of heights,” he summarizes. “But, for some reason, you’re standing on one of the tallest buildings in the city.”
“To conquer my fear,” she says, like he’s being purposely obtuse. She glances back over her shoulder, to the edge of the building. “Actually, do you think you could do me a favor?”
“What?” He laughs, incredulous that she would ask something of him when she isn’t even supposed to be here.
“Yeah, here, just,” she says, unlooping the camera from her wrist and shoving it into his hands. He stares down at it, surprised, and when he looks back up she’s slowly making her way to the edge of the building. He follows after her.
“Hey- what- no!” He calls. “We’re not having some kind of photoshoot. You’re not supposed to be up here.”
“Like you always do what your told,” she says, shooting him a smirk over her shoulder. There’s something devilish there and he realizes she must know who he is. Who doesn’t nowadays? “Just take one photo of me at the edge, okay? And then you can go back to your party and you’ll never have to hear from me again.”
He huffs, annoyed at being given orders, but she reaches the edge and he sees her posture change. Tense once again, now that the reality of her decision is right in front of her. Still, she hesitates only another moment before turning back to him and easing herself up onto the concrete lip. He takes a nervous step forward as she settles into a seated position.
“Just take the picture,” she calls, her voice tight. “Please.”
Frowning down at the camera, he realizes it’s one of those instant cameras. Nothing fancy. He snaps the photo, the flash blinding both of them for a second, and the camera whirrs as it prints out the small picture. The woman pushes off of the ledge, eager to be away from it, and snags the camera from his hand before the picture comes out.
“Thanks,” she offers, the word clipped. He chalks it up to the nerves over what she’d just done and nods. She leads the way back to the door, seeming eager to get off the roof now that she’s accomplished what she’d set out to do. Oliver isn’t sure this could be considered a conquering of her fear, but he’s just glad it’s getting her off the roof.
“Oh, hey, one more thing,” she says as they reach the door. They’re just inside now, at the top landing of the staircase, and Oliver lets the door fall shut behind him.
The woman spins suddenly and, with their proximity, Oliver’s reflexes aren’t quick enough to counter the move. She presses into his space, her hand coming up to land on his bicep as she pushes up on her toes and kisses him. He reacts on instinct, kissing her back before he really realizes what he’s doing.
It’s not the worst thing that’s happened to him tonight.
Behind closed lids, he sees a bright flash and hears the whirring of her camera again. The woman pulls away from him, but the stickiness of her lip gloss lingers on his lips. When he opens his eyes, she’s staring up at him, fallen back down to her usual height. The camera stops whirring, the photo printed, and the stairwell goes silent.
“Uh,” he offers eloquently.
“Thanks again,” she says, shooting him a bright but false smile, and then she darts down the stairs and back out the door.
And Oliver isn’t sure what just happened.
---
Felicity can’t believe last night really happened. The guts, the steel stomach, the absolute balls it took for her to do any of that seems insane. Yet, the proof is sitting in front of her on her desk in the form of two shaky polaroids. The one on the rooftop has her caught, mid-panic, as the wind ruffles her hair and the hem of her coat and her mind runs through all the different ways she could tumble off the building. It’s dark enough, taken far enough away that none of that shows. But she remembers it clearly.
The photo from the stairwell is brighter, but blurred. She remembers her hands shaking, the way she’d needed to take the photo quick. God, she’d really just up and kissed Oliver Queen. What was she thinking? It’ll be lucky if she doesn’t end up fired before her two weeks notice even starts. Her only saving grace is that she’d never introduced herself to him.
He’d probably forgotten about her the moment she’d left his sight.
Someone clears their throat from the doorway next to her cubicle and she startles back to the present.
“Felicity Smoak?” A vaguely familiar voice asks and she looks up. The pen in her hand falls to her desk, rolling across the surface. He smiles charmingly. “Hi. I’m Oliver Queen.”
“I know who you are,” she says before she can stop her stupid, traitorous mouth. She rushes on, “You’re Mister Queen.”
“No,” he says immediately, “Mr. Queen was my father.”
“Right, but he’s dead,” she says, because something about having Oliver Queen standing in her doorway has absolutely fried her brain. “I mean, he passed … I mean-”
She squeezes her eyes shut, sure her face must be the color of her pen by now. One deep breath, count to three, and-
“How did you find me?” She asks. Somehow her inability to act like a normal human being hasn’t sent him running, but she realizes that he could just be here to reprimand her for last night. God, what is wrong with her?
“My family owns the company,” he points out. And, yes, she’s aware. “Which makes it pretty easy to get everyone’s personnel file and their company ID photo.”
“Oh,” she frowns. “Right.”
The room goes silent for a minute and she shoots a concerned glance to the cubicle next to hers. It’s empty. Felicity wonders how long she’d been lost in thought, staring at the polaroids from her adventure last night. At the reminder, she glances down at her desk and hastily shoves the photos into the coloring book next to them.
“Look, I’m really sorry about last night,” she says. “But if you came down here to have me fired, I actually only have about three weeks left anyway so-”
“I’m not having you fired,” he says and when she looks back up at him, he’s smiling at her expense.
“Then, why are you here?” She asks slowly, her face pinching a bit in confusion.
“Did you think I was just going to forget the crazy woman who snuck up onto the roof, kissed me for a picture, and then disappeared?” He laughs.
“I,” she starts, pouting. “Yeah, I was hoping.”
“No such luck,” he sighs.
And then, because he’s Oliver Queen and technically he does own the entire building and everything in it, he circles her desk to the empty cubicle next to hers. She watches as he pulls the computer chair away from the desk, rolling it into the space between her desk and her neighbor’s. Felicity’s sure she must look insane, watching him with wide eyes as he settles down into the chair.
He settles into it with an easy confidence that, she figures, must come from looking like him. The walls around her cubicle are a bright blue and his eyes reflect them, offset by his light grey sweater that only makes them seem brighter blue, make his skin seem just a little more tan than it had last night in the dark.
“You didn’t really answer my question,” she says, snapping herself out of it. Oliver raises an eyebrow at her. “Why are you here?”
He leans forward on the chair, resting his elbows on his knees. Felicity straights up as the movement brings him closer to her, his gaze narrowing in on her.
“You didn’t really explain anything last night,” he says. “So, I’ve just been trying to figure it out and I decided the best way to do that would be to come right to the source.”
“Look, I’m really sorry I kissed you,” she says, deciding to just bite the bullet. “It was incredibly inappropriate and unprofessional. I don’t even have a good reason. But, I swear, it won’t happen again and it’s not, like, a regular thing for me to do. Go around kissing employees of Queen Consolidated. Well, I did go on a date with someone from R&D once, but it was all above board and we didn’t even-”
“What was it?” He asks, blessedly cutting her off. She frowns, confused. “The reason.”
Felicity’s whole body freezes with the question. Of course he’d want to know the reason. She had, without any warning or regard for his feelings on the matter, put her mouth on his. She owes him an explanation.
It’s just that she might die of embarrassment if she gives it.
“It was on my bucket list,” she mumbles, tangling her fingers together in her lap to keep them from fidgeting.
“What?” He asks and the confused way his brow pinches is almost unrealistically adorable. She huffs out a breath, squeezing her eyes shut and repeating herself, louder this time,
“It was on my bucket list.”
The room goes quiet for a minute and, unable to bear it, Felicity peaks one eye open slowly and then the other. Oliver is sitting up a little straighter now, no longer leaning towards her, and the confusion on his face has quickly morphed into something more smug.
“Kissing me was on your bucket list?” He asks.
“No,” she says immediately, defensive. “It was kissing a stranger.”
Oliver hums, sounding unconvinced and she glares at him. Spinning in her chair, she grabs her tablet and unlocks it. The document with her transcribed bucket list is already open and she holds it out for him to see, tapping the edge of the casing next to where “kiss a stranger” has been striked through.
He squints, leaning forward to take an exaggerated look at the screen. And then he swipes the tablet from her hands. Felicity gives an indignant yelp, not having intended to show him the whole list, but the damage is done. Oliver doesn’t seem eager to hand the device back.
“But you knew who I was,” he points out. “Does that really count?”
“It’s close enough,” she grumbles.
“Sure,” he says, like he disagrees but isn’t going to debate it. She’s glaring at him again when he looks up from the tablet, setting it in his lap but not offering it back to her. “So, why exactly are you trying to strike things off your bucket list? Are you dying?”
He’s teasing, she can tell, but she doesn’t appreciate it. What’s more, she doesn’t want to answer. Because it had made sense, when she’d started this. When she’d begun with simple things, scribbled in an unkempt handwriting that hadn’t been fully formed yet, and followed them to the letter. Some she’d already done. Others she hadn’t.
And he’s so irritatingly beautiful, sitting across from her in that soft-looking sweater with light in his eyes. She’s already leaving her job soon. What could they do to her if she were to smack him right now? (What could they do to her if she were to kiss him once more, just to see?)
The errant thought makes her cheeks heat and she wonders if he notices, averts her gaze to the work on her desk she’d been neglecting anyway. The corner of one of the polaroids sticks out of the book she’d shoved them into.
“It’s kind of a long story,” she hedges and maybe he’ll leave. She wants him to, she thinks. Or she wants to want him to. Because if he stays in her space much longer, eyes reflecting the blue of the walls, lips turned up in amusement at her or because of her, it’s going to become too much.
Instead, he shrugs a little and settles further into the chair. As if he has all the time in the world. Felicity is almost certain he doesn’t. There’s a company he’s meant to be grooming for and she’s pretty sure that comes with a myriad of responsibilities.
“Try me,” he says, throwing the challenge down with a quirk of his eyebrow. And she sighs, annoyed but eager to get the encounter over with.
She starts,
“I’m moving in about a month – right after the new year – and I’ve been doing some packing, you know, just getting rid of some old clutter and trying to figure out what to donate, what to box up. And I came across an old box of things from my mom’s and I found this truly awful looking old notebook. I’m talking pink monkeys on the cover and water damage from years of use and abuse and being stashed in my old apartment with the leaky roofs… Anyway, when I was a kid, I started a bucket list.”
“You started a bucket list when you were a kid?” He asks, cutting her off with a quiet laugh. She hates the way her chest constricts with the sound, breathy and sudden, like she’d surprised it out of him.
“I watched a lot of TV,” she shrugs. “ Anyway , I kind of kept the stupid thing in high school and for a while in college. So, I was adding to it every now and then, but I’d pretty much forgotten about it and then I found it. And, like I said, I’m moving and quitting my job and it just- I don’t know, it seemed like a good time. So, I’m trying to finish everything on the list, that’s feasible, before the end of the year.”
Oliver hums contemplatively. He lifts the tablet again and she can see the way his eyes scan over the document. He begins to read some of them aloud.
“Try every type of Pringle,” he starts with.
“They are not all winners,” she says, shuddering at the reminder. He gives that laugh again, but reads on as she nods along to the ones she’s crossed off. Solve a Rubik’s cube. Write a computer code. Buy alcohol. He raises an eyebrow at ‘hack a government agency’ and she gives him a coy shrug.
“Okay,” he says, handing the tablet back to her. “How can I help?”
“Excuse me?” She laughs.
“What can I say?” He asks, holding his hands up in front of him, palms towards the ceiling. “You’ve convinced me. I’m tagging along.”
“What? No, I wasn’t-” She argues, but his phone chimes and he turns his hand over, checking the smart watch on his wrist. She sees his mood shift, his face shuttering as he reads the notification.
“I have to go,” he says, pushing up out the chair. “But, I’ll come by tomorrow at the end of the day and we can get started.”
He’s gone before she has another chance to argue, shock setting in and rendering her silent. He gives her a short wave just before he disappears out of the office and she stares after him, slack jawed.
She isn’t sure what just happened.
---
“Finish a coloring book,” he reads aloud, sitting across from her once more. She still doesn’t love the idea of him seeing her whole list, but has given up on the idea of keeping him away from this. He had, indeed, come back to her office and walked her to her car. And then, he’d suggested she follow him to a little diner a few blocks over.
He rides a motorcycle. Because of course he does.
They’re sitting across the table from each other, in a corner towards the back. It’s away from the wide front window and the door that chimes each time a customer drifts in from the cold. She can hear each sound coming out of the kitchen – the scrapes of knives on cutting boards, of coffee machines working overtime to keep up with the need for a warm beverage, of oil sizzling over heat as cooks drench each food item in it.
Felicity sighs, reaching into her bag and producing the coloring book from within. She sets it on the table between them with a little extra flare and regrets it immediately. The movement causes the polaroids she’d forgotten she’d stuffed within to fall from it and land on the table in front of Oliver.
He picks them up before she can stop him.
“These are nice,” he says quietly and she tries not to analyze the way his gaze lingers on one of them, tries not to wonder if he’s staring at her – pink cheeked and caught in the wind – sitting on the edge of the building. Or if it’s the moment she kissed him, surged up on an impulse of bravery and answered a question that has plagued the office gossip for years; What is it like to kiss Oliver Queen?
Plenty of women in Starling seem to know and now, in a way, so does Felicity.
He hands the polaroids back to her with gentle fingers and she slides them into one of the smaller pockets on her purse. When she looks up, he’s flipping through the coloring book. Most of the pages are finished, she knows. She’s been working on it every spare moment and it’s actually been a great stress reliever as she’s prepared for the move.
“Okay, so you clearly have that one handled,” he says, setting the book down and looking back to the list on her tablet. She itches to take it from him, to delete the more embarrassing entries put in by a teenaged Felicity. “A lot of these are definitely doable. Especially now that you have me in your corner.”
“Lucky me,” she offers glibly and he shoots her a dark look.
“You know, I thought you’d be a lot more receptive to my help,” he says quietly and she can tell, with some regret, that she’s hurt his feelings. Sees him retreat into himself a bit as he twists the string hanging from the teabag in his mug around his finger with ease.
“Why exactly are you helping me?”
“You know us listless billionaires,” he says with a shrug. “Always looking for something to occupy the time.”
He says it easily, but straightens a bit in his chair as he does. Something about the words ring false to her, like they’re a reaction rather than an actual answer. Felicity leans forward, resting her chin on her hand and narrowing her eyes at him. He gives nothing.
And she’d be lying if she said that didn’t pique her curiosity. If she said the way he’d followed her onto the rooftop, searched her out in the Queen Consolidated basement hadn’t made her want to ask about three hundred and twenty questions. But it’s more than that. It’s the easy charm that fades into self depreciation. The way he can laugh at her bucket list one moment and shut down the next based on a notification on his watch.
He might be a mystery. And she might be a sucker. But they’re probably both doomed.
“Okay, fine,” she says, shrugging and sitting back in her seat. “You’ve convinced me.”
“I have?” He frowns, surprised by her sudden change of heart. She figures even he doesn’t believe his own bullshit.
“I know you’re lying,” she says, waving her hand dismissively. Because the lie doesn’t matter. They’re hardly friends. “And I’m gonna figure out why, that’s just a given. But, strangely…”
Now Oliver is the one leaning forward, just a touch, hanging on her words. When she drifts off, his eyebrow ticks up in response.
“‘Strangely’,” he echoes, “What?”
“I don’t know why ,” she admits. “But, strangely, I feel like I can trust you.”
There’s a beat of silence — not real silence, as the diner continues to move around them. And then Oliver smiles at her and it’s different than the man who stands beside his mother at events and press conferences. It’s softer, smaller. Real. Her stomach flips in response to it and, yeah, what was she thinking about being doomed earlier?
“Good,” he says, nodding. “Because you can trust me.”
God, she hopes she’s not wrong.
“ And ,” he presses on handing the coloring book back to her, “I know where we can start.”
“Start?” She frowns.
“With the list,” he says and now the smile is at her expense, she can tell. He’s suddenly reaching into a pocket within his jacket and pulling out his wallet. He pulls out a few bills for their drinks and Felicity would stop him, but he’s literally a billionaire. He can afford her latte.
Then he pulls out a small bit of white card stock and holds it out to her. She recognizes the company-wide branded business card. His name is in all capital, bold lettering, settled dead center. As if anyone wouldn’t know him on sight. There’s no title under it and she wonders if that’s by design or a sign of the limbo he’s been in for months.
“What’s this?” She asks a little dumbly. Stops. Corrects herself. “I mean, why are you giving this to me?”
“It has my cell number on it,” he explains, standing from his chair, preparing to leave her in this unfamiliar diner. “Text me your address and I’ll pick you up tomorrow morning, around ten.”
“Wha-?” She starts, staring down at the card in her hand. Oliver’s movement pulls her focus and she stops him before he can leave. “Hey! Aren’t you going to tell me what we’re doing?”
“Why ruin the surprise?” He shrugs, sending her an easy wink. And then he’s leaving, calling goodbye to someone in the kitchen like he knows them personally.
There’s still steam rising from Felicity’s mug, but she slips the card into the pocket with the photos after a few minutes and follows his lead.
---
Part of her hates herself when she gives in and sends Oliver her address. She half expects it to be some kind of prank. Some way of mocking her that she hasn’t figured out yet. New phone who dis? But Oliver texts back a thumbs up emoji and a smiley emoji and a reminder to be ready at 10am. And, the truth is, Felicity would hate herself more for not taking him up on the offer. Because the whole point of the list is to be spontaneous, to act outside of her norms.
Plus, Oliver Queen has landed himself firmly in Felicity’s mental ‘mystery’ box and she’s always been bad at walking away from those.
He shows up at 10:32 and she’s significantly annoyed with him from the jump.
“Are you ever on time?” She bites as he meets her on her front porch. Her frustration is more with the situation. With the fact that, during his 32 minutes of tardiness, she had talked herself in and out of cancelling so many times that her anxiety nearly had her running back upstairs to hide under her blankets.
He frowns, most of the expression hidden beneath his sunglasses. Still, Felicity sees the moment her bad mood infects him. His posture changes, shoulders tightening, and a muscle in his jaw ticks. She can almost imagine the sound of his teeth grinding together.
“Pretty much,” he grumbles, except it’s much more of a pout and it’s stupid that that alone makes her want to forgive him.
“Are you finally going to tell me where we’re going?” She asks instead. Oliver doesn’t answer, waving at the sporty looking car in her driveway and ignoring the question.
“I brought you coffee,” he says, turning and retreating to the car. Felicity considers, once more, just to say she did, calling the whole thing off.
She doesn’t. And he did bring her coffee. It’s black and terrible, but she says thank you because she has manners and manages to drink half of it as they make their way out of the city. The longer they drive on the interstate, the more her anxiety builds. She finishes a page and a half in her coloring book before the movement of the car begins to make her nauseous.
“Oliver, seriously,” she says once the coffee has made her jittery and they begin passing mile markers she’s doesn’t recognize. “ Where are we going ?”
“You’re impatient,” he says, surlier than she expected him to be. Where is the light, charming man who’d wandered into her office? She huffs, annoyed that he expects her to be so easily taken by him.
“A man I just met two days ago has somehow conned me into some sort of road trip with him, outside of the city, and won’t tell me where we’re going,” she argues. “I don’t even recognize this interstate anymore.”
“That’s,” he starts, sounding like he might argue, but then he sighs and finishes with, “Fair.”
She gives him a sarcastic smile. He ignores it.
“My parents have some friends who own a winery out in Woodinville,” he explains. “I figured we’d take a tour.”
“‘Go wine tasting,’” she sighs, sitting back in her seat. The addition to her list had been one she’d written while in college. After a night of cheap wine and Thai food, she and Cooper, her boyfriend at the time, had sworn they’d go tour a winery one day. She’d said something about it seeming romantic, he’d suggested it was a good way to get drunk.
They never made it anyway.
“It’s on your list,” he adds, unnecessarily. Like she doesn’t basically have the thing memorized by now. She’d stared at it for weeks after she found it, trying to figure out what to do with it now that she had it again.
“Yeah, no, I know,” she says, shifting in her seat. “It’s just…”
“Just?” He prompts, shooting her a look when she lapses into silence.
“It’s stupid,” she says. “But, when I wrote that, I thought I’d be doing it with someone else.” She flinches. “ It being going wine tasting, not, you know, any other… its.”
Felicity squeezes her eyes shut, unsurprised by Oliver’s silence. How does one even respond to what she’s just dropped on him? She can’t imagine any way for him to take it other than a) she doesn’t want to be here with him and b) she literally cannot control her fucking mouth. And, on that note, her mouth begins running again.
“I’m sorry, I didn’t mean it like- I mean, I’m appreciative of you taking me to this place. I’m sure you had to call in a favor and it’s probably nicer than any place I could afford. Which isn’t to say that’s why I’m glad you’re taking me, I just mean- well… You know, you can stop me any time you like.”
“I was actually waiting to see how long you could go without taking a breath,” he says, dryly and it takes her a moment to realize he’s teasing her. She deflates some, trying not to pout but knowing exactly what it looks like as she slouches back into her seat.
It would be lovely if they could go more than ten minutes without one of them offending the other.
“So, who was it?” He asks, softer this time and she knows he’s trying to get back in her good graces. She tries to decide if he’d ever been there in the first place. The stairwell kiss comes to mind. “The person you thought you’d be going with?”
“Oh, just my boyfriend from college,” she shrugs, hoping not to make it sound like more than it is. It’s not like she’d want Cooper to be here for this, she hasn’t even really thought about him in years. But he’s just another failed relationship to add to her growing pile. One more person she’d let herself dream of forever with before ultimately ending up heartbroken.
She presses on, “He was kind of a dick, though. His whole thing was that wine was too girly and he only drank it when he was with me because it made me-”
Felicity stops, her mouth snapping shut as she swallows the rest of the sentence. She’s suddenly painfully aware of who she’s talking to and how very little they know about each other. Oliver frowns, but doesn’t look away from the road. The conversation with Cooper had been so long ago and she just sort of remembers it in that way you remember something hurtful someone said about you, even if you brushed it off as a joke.
Not that Cooper had meant the comment as a slight. Just that it had made her self-conscious about her love of wine for a few weeks following. And when she’d started dating after him, had kept herself to other beverages with dinner for a while.
“Made you what?” Oliver asks and it’s innocent she knows, because how could he know what her tool of an ex-boyfriend from when she was practically still a teenager had said. But, god, she didn’t mean to actually tell him.
“Um,” she stalls. “Flirty. I guess wine makes me flirty.”
Horny had been Cooper’s word, but she doesn’t really know Oliver that well. It’s not that she didn’t know the drink made her a little extra frisky, but Cooper had hardly needed the help in getting her to sleep with him back then. Still, she wishes she didn’t remember the conversation from so long ago, really wishes she hadn’t accidentally brought it up now.
Oliver clears his throat, shifting in his seat and she wonders if he understood the underlying context despite her efforts.
“Well, I’ll make sure you keep your hands to yourself,” he says simply, his fingers flexing on the wheel. He glances over at her, winking, and she flushes. She sinks down into her seat and glares at the unfamiliar mile markers as they pass, hoping they aren’t terribly far from the winery.
---
The winery Oliver’s family friend runs isn’t busy, which is good, but it also isn’t very well heated, which is bad. Felicity figures that December isn’t exactly a busy time for tours and they must not keep the heat very high, especially in the cellars where the wine actually is.
There’s a few other people in the group. An older couple leads the group, their arms linked together as a guide leads them through the expansive building and tells them about each glass they’re handed. A group of young women that Felicity would guess are college students on break giggle and clink their glasses together, taking delicate sips and saying things she’s sure they learned from TV.
For his part, Oliver is mostly quiet. He’d chatted with the older woman when they’d arrived, charming as ever. Felicity doubts he doesn’t see the glances he earns from the group of girls in front of them, but he doesn’t comment or feed into it. He asks her opinion on each of the wines they try. She admittedly knows very little about fine wine other than each glass tastes better than the last.
Towards the end of the tour, their guide leads them into a large room with plush looking couches and a bar at one end. There’s a fireplace burning on one side of the room, but the older couple quickly take up the real estate near it. Oliver leads Felicity towards the bar instead.
“Pick something,” he directs as they settle onto their stools.
“What?” Felicity frowns.
“My treat,” he says, waving a hand towards the wall of wines on display. The bartender, free of any other guests to serve, hovers near them. He drops his voice, “And, before you argue, this whole tour was free. Let me buy you a glass of wine.”
She holds his stare for a minute, still prepared to argue, before sighing. “Fine. That rosé we tried would be nice.”
Oliver looks over at the bartender who’s already moving towards the shelf, clearly knowing which wines are offered on the tour.
“So, how did I do?” He asks, once the wine has been opened and poured into glasses in front of them. Felicity makes a show of swirling it in her glass, the way she’d watched the older couple do with each glass they had been handed on the tour.
“‘Do’?” She echoes.
“With your first wine tasting? Did it live up to your expectations?”
Felicity hums, pretending to consider the question with some degree of seriousness. She takes a long drink of the pink wine from her glass. The movement leaves behind an imprint of her lipstick on the clear surface.
“I guess it’ll do,” she sighs dramatically, dangling the glass between her fingers. He stares at her for a moment and she gives in, winking at him. It earns her a short laugh and a small shake of his head.
He moves suddenly, pulling his phone from the pocket of his jeans.
“Hold still,” he says and Felicity frowns. Oliver holds his phone up and she realizes he’s taking a picture. The silly polaroid camera she’s been using for her pictures is tucked into her purse, but she indulges him, holding the glass up a little higher and looking off as if he’s captured her in a candid moment.
“How’s it look?” She asks once he’s lowered his phone, looking at the photo they’d staged.
“It’s perfect,” he says, setting his phone down and lifting his own glass. He holds it out and she knocks hers gently against it.
Maybe it’s the wine, but perfect feels like a pretty good descriptor.
---
Oliver suggests they try to mark one or two things off her list every day. Felicity suggests that they should probably get to know each other a little better if he’s going to insist on spending every day with her from now until they finish the list. He seems hesitant at the prospect, as if getting to know her – or maybe her getting to know him – makes him want to squirm right out of his skin. But she’s the one with the list, so he agrees.
The day after the wine tasting, he shows up with a thousand piece puzzle and a bottle of red wine. Felicity splits the evening between working on the coloring book, putting the puzzle together with Oliver and trying to learn more about him.
She finds the latter to be increasingly difficult. Felicity is somewhat of an open book, even when she doesn’t want to be. It’s a nerves thing. She talks when she’s uncomfortable and, well, she’s often uncomfortable. Especially with Oliver. He puts her off balance just a bit.
It’s strange and uncomfortable, but she’s not sure it’s a bad thing.
He, on the other hand, is much more monosyllabic than their initial encounters would have made her believe. Even as the wine bottle empties and the puzzle is a little over halfway assembled, she feels like she’s learned nothing about him that she couldn't have found from the Queen Consolidated website or a gossip rag.
By the end of the night all she’s learned about Oliver is that he’s not nearly as outgoing and friendly as his insistence on following her around on her bucket list adventure may have insinuated.
He’s also irritatingly good at everything .
“You swear you’ve never done this before?” She asks, glaring down at the burnt food in front of her on the counter. “No secret sessions with five-star chefs? You didn’t used to help with dinner as a kid?”
“Felicity, I grew up with a household staff,” he frowns. “I didn’t help cook.”
Even as he says it, he takes the handle of the pan in front of him and flicks his wrist. The perfectly colored pancake lifts, flips in the air and lands back on the teflon surface. She could punch him. He turns to look at her with a proud little grin and finds her staring sourly at him.
“You can’t be mad at me for this,” he pouts. “It’s your bucket list.”
Felicity lets out a quiet, nonsensical grumble and takes a spatula to the burnt pancake in her pan. It sticks to the teflon as she scrapes at it. She’s pretty sure the whole point of teflon is that it’s not supposed to let food stick to it.
“That’s very impressive, Oliver,” the woman teaching the cooking class says, moving down the aisles in her personal monogrammed apron.
Felicity doesn’t hate her for any reason other than pettiness at anyone who can cook better than her – which is apparently everyone. But she also hasn’t missed the way the woman’s eyes rove over Oliver each time she comes by to pay him a compliment, nor had she been able to ignore the way she’d wrapped her hand around Oliver’s on the handle of the pan as she’d shown him how to flick his wrist to properly flip the pancake. A treatment she had very much not given Felicity.
She’s well aware jealousy is a truly terrible look on her.
Oliver’s wall of charm goes up and Felicity realizes she’s beginning to tell the difference between his real charm and the kind he uses when he’d rather be anywhere else than engaging in social interaction. Or maybe it’s wishful thinking in the way she sees his shoulders tighten under their instructors attentions, his fingers tightening on the pain as he shifts uncomfortably. Still, he offers her a kind smile and thanks her for the compliment.
She moves on and Felicity goes back to hacking at the burnt pancake batter sticking to her pan. A flash to her right startles her, pulling her attention.
“Hey!” She cries, finding Oliver holding a polaroid in his hand, waiting for the ink to form into an image. He must have retrieved the polaroid from where she’d set it on top of her bag and it now dangles by its strap from his wrist. She glares at him.
“What?” He laughs, and even when it’s at her expense she appreciates the sound. “You wanted pictures.”
“Not of the failures,” she pouts, giving up on salvaging the pan and letting it drop to the stovetop. It gives a clatter, but no one else in the room seems to care.
“The list said ‘take a cooking class’,” Oliver sighs. He gives the polaroid a shake before aborting the movement halfway through, presumably remembering how Felicity had yelled at him for it the last time he’d done it. “Not ‘become a five star chef in one afternoon.’”
“Easy for you to say,” she complains, stepping away from her stove to wander towards his on their shared counter top. She takes a fork from the pile of utensils and picks at his perfect pancake, cooling on a plate now. She takes a bite and frowns down at it. “Did you put cinnamon in this? She didn’t even tell us to do that!”
“Felicity,” he says gently, taking the fork away from her and tucking the polaroid into a pocket on his coat. “Forget the pancakes. Regardless of how well you did, the point was to do it and you did. Not everything is a competition.”
She pouts. “You clearly don’t know me very well.”
It’s not meant to be a real indictment of their knowledge of one another, but she regrets it as soon as she sees his face fall. It’s a subtle shift and gone as quickly as it comes, replaced by one of those easy false smiles he’s so good at. He leans down, returning her camera to her bag and holding it and her coat out to her.
“Well, either way, I’d call this a success,” he says. “Let’s get out of here.”
She lets him help her into her coat as they thank the instructor for her time and apologize for the mess Felicity has left her with. She waves it off, but Felicity wonders if she’d be as forgiving if it weren’t for Oliver standing next to her.
“Are we done for the day?” She asks as they make it out of the warm building and into the brisk December air. Light snow falls from the sky, not quite strong enough to stick but it clings to the fabric of Felicity’s scarf, catches in her hair.
She doesn’t mean for the question to sound so disappointed. Oliver turns to look at her and the way his mouth has turned up at one corner, smug but trying so hard to hide it, lets her know it hasn’t gone unmissed.
“Not quite,” he says. “I thought we could get a drink. There’s a bar I like not too far from here.”
Felicity freezes for a moment, her brain jumping to overthink the invitation. It’s not like they haven’t drank together before – at this point they’ve nearly shared more wine than they have words – but there’s something about the invitation that makes her feel she should tread lightly. Oliver notices her hesitation.
“If you’d rather not-”
“No!” She says, a bit abruptly, cringing at herself. “Sorry, no, of course. I’d- yeah, I’d really like that.”
His face brightens, a wide smile overtaking his features and she’s suddenly so glad she said yes. Even with her hesitance about whatever intentions Oliver may have, that smile on his face – real and bright, making him look young and even more handsome than usual – is well worth whatever trouble he may bring.
Which is probably a very bad sign for her.
---
Felicity doesn’t know why she put it on her bucket list, really. It’s just that, at some point, she’d decided that it was the Grown Up thing to do. To go to a bar and, very specifically, order an Old Fashioned. She doubts she’d even known what was in the drink when she’d scribbled it down in her notebook.
She’d always imagined herself bathed in black and white, like the heroine in one of those old movies she’d stolen the idea from. Settling onto a stool at some fancy bar, long legs and styled curls, pulling eyes and attentions throughout the room.
Instead, she’s wearing a simple skirt and there’s snow stuck in her curls, the wind having whipped them into some kind of mess she can’t worry about. The bar Oliver has brought her to is quiet, nearly empty, and far less fancy than she’d have expected of him. But she slides onto a barstool and crosses one leg over the other. The bare state of the room means she gains the bartender’s attention immediately.
“Can I get an Old Fashioned?” she asks, like it should be something exciting and dramatic. The man behind the bar only gives a nod and moves to make the drink. She frowns a little, feeling childish for thinking it should have been more.
Oliver had hung back towards the door, but he joins her now, sliding into the space between her and the barstool next to her. He settles an elbow on the bartop, and ignores her for a moment, as if they’re strangers rather than two people who’d come in together. She bites down a laugh at his dedication to the moment, as she had done her best to explain why ‘order an Old Fashioned’ had shown up on her list.
When the bartender returns with her drink and gives her the total, Oliver cuts in.
“It’s on me,” he says, already sliding a black card across the wooden bartop. Felicity rolls her eyes, but pulls the drink towards her. “I’ll have a vodka soda.”
The man doesn’t seem to care who’s paying so long as someone does and takes Oliver’s card. Oliver turns towards her now, still in the space between the two seats. The fabric of his jeans scratches against the bare skin of her calf with his closeness.
“Go on,” he prompts. “Big moment here.”
She sticks her tongue out at him, but shifts the glass closer. He’d laughed at her on the way over, not meanly, but in that confused way he has when she’s managed to bewilder him, and asked if she’d really never ordered the drink. Honestly, Felicity couldn’t remember ever having done so, so it was better to be thorough.
And he’d played along so easily, eager to try and make the moment live up to her fantasies.
Felicity makes a show of it, swirling the glass to make the liquid and orange slice within spin inside. She sniffs it, holds it up in a cheers motion to Oliver who’s own drink has just been delivered, and then takes a sip.
And immediately recoils. Turns out, she’s still very much not a whiskey girl. She swallows the drink down, not wanting to make a show of her distaste for the whole bar to see, but Oliver notices. He chuckles and gently takes the glass from her, swapping it out for his vodka soda.
“I probably should have expected that,” she admits, letting out a small laugh. “I’ve never been much of a whiskey drinker.”
“Well, lucky for you, I am,” he says. “I took a chance with the vodka soda, though.”
“It’s perfect,” she assures him, happy to wash the taste of the whiskey down with the citrus-y vodka. “Wait, what about my picture?”
“I already got it,” he says, fishing the orange peel out of his hand-me-down drink and setting to the side on a napkin.
“You did?” She frowns.
“I took one while you were ordering,” he explains, wiping his fingers on the napkin. He unzips his coat pocket, pulling two polaroids from within and setting them on the bar top.
The first is from the cooking class and Felicity cringes at the sight. She’s glaring down at the ruined pancake, her tongue sticking out slightly as she scrapes at it with her spatula. It’s not her finest moment but maybe she’ll laugh at it some day.
The old fashioned photo is a little darker, taken from a further distance as she sits at the bar talking to the bartender. She has to admit, Oliver has some level of artistic eye. It’s not black and white or anything like she’d imagined, but she’s bathed in the golden light of the bar and her crossed legs look amazing. She’d almost call it a shot from a movie.
“Do you just want to follow me around taking pictures of me forever?” She teases, running her finger over the edge of the polaroid.
Oliver just shakes his head at her, a small smile lighting his features as he finally settles into the seat next to hers. It pulls him out of her space and Felicity finds herself surprised at how much she hadn’t minded him there.
They stay for a few drinks, not doing much more but continuing to scrape the surface of getting to know each other. Felicity pulls her tablet out to scratch the things they’d done over the day off her list.
Oliver looks it over again, teasing her about some of the more childish things. She tries not to blush when he reaches the risqué parts of the list, added during college when she’d watched too many movies and had too little sex. She laughs them off, commenting that obviously only some parts of the list are attainable. Oliver seems more flustered by her list than her which she finds oddly endearing. Still, she forces them to move on.
“Can I ask you something?” He asks quietly, once they’re into their second round of drinks and have put the list away once more. Caught off guard, because that’s usually her line, Felicity simply nods. “What’s the deal with the list? Really, I mean. Why try to finish it now, by the end of the year?”
“The truth?” She prompts, though it’s more of a stalling technique.
“The truth,” Oliver nods, seeing right through her she thinks.
Felicity takes a sip of her drink instead of answering right away, trying to decide how much to tell him. In this case, at least, she wants to be careful. Because she’s given so much more of herself to him than he has given of himself in return and it’s not a big deal usually, because she always gives more of herself to people than she intends to. But, this? It’s more than fun facts about herself and little tidbits she might tell anyone.
Finally, she gives in.
“The truth is,” she starts, twisting her glass and watching the ice rattle within. “It’s been kind of a rough year for me. I was in a serious relationship and, well, that ended which was hard. Then I found out that my supervisor has no intention of ever submitting me for promotion review – mostly because he knows I’m wildly more competent than he is – which means that I had set myself up to be trapped in this dead-end, but pays well job for the rest of my life, just absolutely wasting my skills and degrees.”
She stops for a breath when she realizes she’s gone off track and probably shouldn’t be ranting about incompetence to the future CEO of the company.
“Anyway,” she goes on, shaking her head at herself. “It got me to kind of evaluate things and I realized, I don’t really have anything in Starling to keep me here. All of my friends are work friends or they were my boyfriend’s friends. I was never that girl who had a ton of people around her, but I was never the type of girl to define myself by one thing or one person, either.”
She bites down on her lip, shooting a furtive look over at Oliver. His eyes are on her, caught up with her words. Maybe there should be some sort of regret for having shared so much, but she can’t find it. Felicity reaches for her drink again.
“Long story short, I realized I needed a change,” she finishes, running her finger over the lip of the glass. “So, I applied to a few places that had been trying to poach me away from QC and signed onto a job. Then, like I said, I found the list while I was packing and – it’s stupid, I know – but I thought that this could all be a part of my new start, you know?”
“That’s not stupid,” he says, shaking his head as Felicity looks back over to him. “I think we all want to believe it’s not too late to be a different person than we have been.”
“Yeah,” she breathes.
Suddenly, his eyes on her become too much and she has to look away. Across from her, behind the lines of bottles of alcohol, a mirror reflects them back at her. Oliver’s gaze it still on her, but it moves away, onto his own drink – a short tumbler of whiskey now, rather than an Old Fashioned. Felicity lifts her glass of vodka and soda water, watching herself take a drink.
She clears her throat, setting the glass back down and turning to him once again.
“So, what about you?” She asks. “What really made you track me down after the rooftop and start following me around with this?”
Oliver doesn’t seem surprised to have the tables turned on him. Rather, he turns on his seat so he’s facing her more fully, his knee knocking gently against her own where her legs are still crossed over one another.
“I don’t know,” he says and, in any other instance, she might consider it a stall. But the openness in his gaze, the earnestness there, makes her believe that he really doesn’t understand it either. “I just saw you on that rooftop doing this absolutely insane, incredibly brave thing and… there was just something about you.”
“I was about to puke on your shoes,” she points out, laughing a little and tucking her hair back, trying to deflect the compliment.
“I thought you were remarkable,” he says resolutely and Felicity’s breath freezes in her chest for a moment. “I just… I felt like I could learn something from you.”
“Learn what?” She presses, unable to save herself from her own curiosity. At that, Oliver frowns and it’s his turn to shift his attention, looking away from her. But Felicity can’t take her eyes off of him now.
“You’re not the only one trying to redefine yourself,” he admits quietly, nearly lost in the generic bar sounds around them.
Felicity considers him for a moment before she says, “Well, you’re right. It’s not too late to be different.”
Oliver looks back over at her, something like surprise in his eyes, and offers her a small, grateful smile. She doesn’t even mind it when they finish their drinks mostly in silence. Oliver switches to water while Felicity orders one last drink, realizing they’ve spent longer in the bar than they had intended. When Oliver drops her off at her house, it’s normal. She doesn’t contemplate the weirdness of him walking her up to her door until they’re standing on her porch, awkwardly shuffling their feet in front of one another.
“Well, thanks,” she says. “Despite my burnt pancake, I’d call today’s events a success.”
“Good,” he smiles. Then he pats his pockets, pulling the photos he’d taken of her out of one of them and holding them out to her. “Here, you’re gonna want these.”
She thanks him again, taking the photos and admiring the one from the bar once more. She can feel Oliver’s eyes on her.
“You know, Oliver,” she starts quietly, looking up at him again. “Whatever kind of person you were that you think you need to reinvent yourself from, who you are now I… I think you’re remarkable, too.”
He seems caught off guard by the words, his brow pinching a bit in surprise as he stares down at her. She almost takes it back, unnerved by the silence she’s created between them, but Oliver’s hands come up to the sides of her face, palms curving around her jaw, and he kisses her. His lips taste like whiskey and bitters, but Felicity is suddenly not as opposed to the taste as she’d been a few hours ago.
“I’m sorry,” he whispers when he pulls away, the kiss ending nearly as quick as it had begun. “I’ve just been wanting to do that.”
Felicity barely waits for him to finish speaking before she’s pressing up on her toes, grabbing onto the lapel of his coat with the hand not clutching the small polaroids and pulling him back towards her. He sways on his feet, bending to meet her in a second kiss. She presses a little harder and this kiss is much heavier, lasts longer than the first.
Until she remembers herself and she’s pushing lightly at his chest instead, trying to create some space between them. Oliver moves as soon as he feels the force of her hand on his sweater, but he stays in her space, breathing a little harder to match Felicity’s own heart rate. He smells like pancake batter and something woodsy and she can’t bring herself to pull further away from him.
“I can’t,” she breathes, the words shaking with her breath. “I’m leaving and I just, I can’t get caught up in something messy like a relationship.”
“I don’t really believe in those anymore,” he admits, but it doesn’t sound like a brag or a tactic. It sounds like lost faith and Felicity aches for him, for the way the sentiment echoes inside of her own chest. “And, I can’t really handle one right now.”
“So, what does that mean?” She asks, her fingers tightening in the fabric of his sweater again. She should move. She should pull away and they should forget this, forget her whole list, before they do something stupid. But she doesn’t.
“You’re leaving,” he repeats and she hums in acknowledgement. “And I’m not really good at relationships anyway.”
Something stupid like pushing him up against her front door. Stupid like inviting him inside, leading him down the hallway. Stupid like…
“If we both know this can’t go anywhere,” she starts, a little leadingly. “Then, what’s the harm, right?”
Oliver only kisses her again in response.