It starts in a bar at three am.
The lights are low, the drinks are flowing, and bodies press up against each other on the dance floor, a pulsating beat thrumming through their veins.
Oliver is reeling from walking in on his girlfriend in bed with his best friend and Felicity is recovering from the grief of Cooper’s suicide in jail.
Neither of them is in a good place and both of them are drunk.
It should’ve been a one-night thing, but the pull was too tight, the chemistry so palpable that neither could leave it alone. If they’re honest, it’s easy, and easy is what they both need. Each night finds them coming back to each other and the nights blur into days as they bury their pain in the feeling of euphoria they find in each other’s beds. They don’t let it die when they perhaps should have… and that’s what leads to the initial downfall.
There’s not much screaming the first time, a few tears on Felicity’s part, a tortured expression on Oliver’s face, and they leave each other. Felicity jumps on a train to a new city and Oliver slinks back to his parents’ mansion.
If they’d concentrated a little more on talking and less on feeling, they might have known that their supposed escapes from one another actually led them to the exact same place.
It’s a few months before they run into each other again.
Oliver’s grabbing coffee just down from his parents’ company and Felicity has rushed out of the office on her lunch break for her fifth caffeine dose of the day. He literally walks into her and their eyes lock, panic setting in across both their faces.
They exchange polite pleasantries, that awkward air hanging between them. Oliver looks Felicity up and down, noting how incredible she looks in business wear, a far cry from the crop tops and cargo pants of their first foray. Felicity takes note of how Oliver’s arms appear to have doubled in size and she can’t help but think what it would be like to be wrapped up in them once more.
It takes them five hours to find themselves making out in the alleyway next to Oliver’s friend’s bar.
They don’t learn from their mistakes. There are not introductions to friends or deep conversations, it’s just sex, something to lose themselves in, a distraction from the world around them. Felicity hits him up after a long day at work and Oliver shows up at her doorstep after a lecture from his parents about his future not going anywhere. It’s as easy as it always was, and it falls apart just as simply.
Felicity starts going to a coffee shop across town and Oliver changes his grocery store. It’s almost effortless for their lives to continue separately.
Felicity gets promoted and then promoted again.
Oliver drinks himself into a stupor and yells at the paparazzi.
She finally settles into the life she’s always dreamed of, VP of a tech company, not having to worry about where her next meal is coming from, finally a sense of stability in the world.
He shirks any sense of responsibility, pushes away the stability Laurel so desperately tries to push onto him, he dreams of finding a purpose.
He throws away every tech magazine he sees in his parents’ house with Felicity’s name in it.
It’s a few years later that they cross paths again.
It’s an unfortunate coincidence to them both when it happens. Felicity cannot put off working with his parents and their company and Oliver knows he’ll be cut off if he keeps refusing his dad’s meeting. His father wasn’t to know their history when he planned said meetings back to back.
“Oh! Oliver!” Felicity gasps as the door she’s been waiting outside opens to reveal the ghost of her past.
“Felicity, I… what are you doing here?” Oliver takes her in, his eyes widening at the sight of her. Of all the places he’s imagined running into her, the small hallway outside his father’s office really wasn’t one of them.
“We’re collaborating with your parents’ company on our new smartwatch, I have a meeting with your father,” She explains as she stands, smoothing over the unseeable creases in her black pencil skirt.
“Right, of course. I… You look good,” Oliver comments, unable to hold himself back, and Felicity feels the blush spread across her cheeks. He notes with a small smile the bright pink flowers on her blouse and the matching color on her lips and nails. He appreciates how even in the strict world of CEOs and VPs, she finds a way to still be her.
“So do you, you always do,” Felicity nods, her eyes searching over his tight shirt and dress pants with a dark look.
“I’m no high-flying executive,” Oliver waves her off, shaking his head and Felicity chuckles a little.
“Please, we didn’t really talk much either time around but I know this life is the last thing you wanted for yourself,” She notes but the way he freezes, an unreadable expression crossing his face, gives her pause.
“Back then maybe.”
“Right, of course, it’s been a long time,” She nods, an embarrassed blush spreading over her features.
Oliver watches her, a warm feeling spreading through him at the mere sight of her before him. Maybe it’s the tough conversation he just had with his father, maybe it’s the inspiration of wanting to make better choices, or maybe it’s the what if that’s been chasing him since their last foray, but he cannot help the next words he blurts out, “You know, maybe we should rectify that whole not talking thing.”
Felicity freezes, her eyes blowing wide as she looks over at him, her heart hammering in her chest, “Do you… do you really think that’s a good idea?”
“I’m not great at those sorts of decisions but I know that I still think you’re as gorgeous as the first time I saw you,” Oliver charms, enjoying the blush that darkens over her cheeks.
“Dinner, just once, and then I’ll let it go forever,” He assures her and he means it. He thinks maybe he should’ve given her more of a chance back then.
“Okay,” She nods, her feet shuffling a little awkwardly in her sky-high heels. “Do you need my number again? It hasn’t changed.”
“No, no, I still have it,” Oliver admits with a small blush. He’s avoided all mentions of her since their last tryst but deleting her number off his phone has been the one thing he’s never quite been able to do.
“Okay, cool, I’ll await your call. Not that I expect you to call me right away or anything but like, I suppose we need to organize said dinner and I…”
“Felicity, I’ll call,” He chuckles, interrupting her charming rambling with a smile and she takes a deep breath, a small smile spreading across her own pretty features.
“Miss Smoak? Mr. Queen is ready for you now,” His father’s executive assistant calls from her desk just around the corner and Felicity blinks a few times before she turns to pick up her laptop and notebook sitting on the chair next to her.
“Of course, thank you. I’ll see you later,” She nods, a smile pulling at her lips as she steps towards the door Oliver just exited.
“See you later,” Oliver grins, watching her disappear into his father’s room before he heads to the elevator himself, a light feeling in his chest for the first time in a while.
This time is different from the last, enormously so.
There are dates and conversations and whispered confessions in the middle of the night about thinking they may finally feel content. It’s a whirlwind of a romance, far deeper and more meaningful than anything they shared in the past.
Oliver learns all about Felicity’s childhood, learning about computers from her father, the pain of him leaving, and the constant fighting with her mother. He learns why she’s so determined to make her own way in the world and appreciates her fight and respect for herself so much more for it.
Felicity learns about Oliver’s early days, his first meeting with Tommy and their lifelong friendship, how his parents have pressured him from day one to be the rightful heir to take over their legacy. She learns the extent to which he just adores his baby sister, Thea, and the lengths to which he’ll go to keep her safe. She understands his rebel ways a lot more as he talks through his fears of ending up just like his parents.
They understand each other.
But that doesn’t stop them from falling apart.
They’re still at wholly different places in their lives. Felicity is building her legacy and Oliver’s still running away from the one that’s been built for him. As much as he understands why she’s so determined and as much as she gets his wish to distance himself from his family, their schedules and priorities are altogether entirely different.
They’re never free at the same time, Oliver partying into the early hours of the morning and Felicity working through the days, and Oliver’s want to always go out starts to grate on Felicity, who after long days at the office is more inclined towards a quiet night in.
It blows up in their face one night in June when after Felicity gets back from work at eleven, Oliver’s on his way out the door.
“What do you mean you’re going out?” Felicity rounds on him as she kicks off her heels, her brow furrowing as she lingers next to the island in the kitchen.
“I said I’d met Tommy, I thought we were going to go out tonight?” Oliver questions, looking at her as if she’s grown two heads, and Felicity groans.
“Well yeah, but that was before I got stuck in the office for fourteen hours?”
“Sorry, I just thought we had plans already,” Oliver shrugs, gesturing towards the door.
“I know we did but I had to stay,” Felicity explains with a bite to her voice, not liking the insinuation behind his words.
“I get that, I didn’t say I didn’t,” He counters quickly, holding up his hands as if in surrender.
“But you still want to go out,” She repeats, looking at him quizzically.
“Well, that’s what we said we were doing.”
“And you don’t think after a fourteen-hour day I might not want to go partying?” Felicity hums, tugging the tight ponytail out of her hair and running her hands through her curls. She honestly forgot she agreed to meet Tommy tonight but there’s nothing worse she can think of than a dark, smelly club right now.
“You never want to go out anymore,” Oliver states blankly and Felicity scoffs, her head wildly shaking as she tries to wrap her head around what’s happening. How can he not understand that after the day she’s had, the last thing she wants to do is put on a tight dress and go spend the evening crammed in a tiny space with a bunch of strangers?
“Well, you never want to stay in,” She counters and Oliver scoffs at that, rolling his eyes.
“Excuse me for wanting to spend some time with my girlfriend,” He bites and Felicity blanches, almost choking on the air as she stares at him with a ludicrous expression.
“That’s all I want to do, spend time with you. Here, at one of our houses, and not in a dark club where I can barely hear you over the bass,” She answers him curtly, crossing her arms over her chest and leveling him with a look.
“I promised I’d meet Tommy,” Oliver tells her after a long pause as he takes a step towards the door.
“You’re seriously going to go?” Felicity questions, already feeling the tears forming in her eyes.
“We were going to talk about something important tonight. You know, if I can hear him,” He throws her words back at her before he pulls on his jacket, the door shutting loudly behind him.
“What the frack just happened?” Felicity questions to herself as she feels the tears run down her cheeks.
She doesn’t linger long. She collects every remnant of herself from the apartment and leaves a note asking him not to contact her.
They both cry alone in their rooms at night for a week wondering how on earth they got so disconnected.
The question of what if follows them around every day.
It’s another three years before it happens and it comes with the most terrible news.
Oliver’s parents both killed in a freak car accident, leaving custody of his sixteen-year-old sister, Thea, to a grieving twenty-something Oliver who has no idea what he’s doing. Their shares in the company and his father’s position of CEO are also bequeathed to him, leaving him feeling like a fish out of water as he tries to navigate running a company and parenting a teenager all at once with no previous experience.
He leaves his partying behind, the paparazzi catch glimpses of him at galas and heading to meetings in the business district but never at the clubs. He spends his days in meetings and on calls, desperately trying to keep his parents’ legacy afloat. His nights are allocated to Thea, where more often than not, he holds his baby sister as she cries, the sixteen-year-old struggling perhaps more than Oliver to understand their parents’ death.
He doesn’t know why he does it. Maybe it’s because he’s been thinking a lot about what could’ve been a lot recently. If he’d grown up a bit sooner, taken the opportunities before him… if he’d been a bit more prepared for a situation like this. He thinks of when he was happiest and there’s one person who stands out the most.
Which is why he sends her the message.
Hey, I know you asked me not to contact you but I can’t stop thinking about you lately. I’m sure you’ve heard the news, it’s made me reassess a lot about my life, and I realize now I was such a fool. I’d love to meet up for a coffee sometime to talk things through but I totally understand if not.
He expects her to ignore the message, to carry on living her life as Oliver knows he probably should with his.
But the reply comes through nonetheless.
Benjamin’s on 8th. Wednesday 1 pm. I have an hour for lunch.
It’s curt but it’s an opening, one Oliver knows he can’t miss. He rearranges his day and makes sure he’s there ten minutes early to claim one of the quieter booths in the back facing the door.
He spots her the second she enters.
Oliver knows that Felicity has only been rising in the industry. With each new project she heads up at Palmer Tech, she gains more traction and attention from tech magazines and the public in general. She moves with a more confident air than she did three years ago, a sway in her step that asserts her place as she moves through the coffee house. Oliver cannot take his eyes off of her as she orders an iced coffee and makes her way over, slipping into the booth opposite him.
“Hi,” He greets a little nervously but the small smile on her face puts him at ease. He couldn’t tell from her text whether his invitation was well-received, but he’s glad to see she’s not glaring at him from the get-go.
“Hi, I um… I was really sorry to hear about your parents,” Felicity starts softly off the bat and Oliver takes a deep breath. He’s heard those words a lot over the past few months but they feel the most sincere coming from Felicity. The gentle look in her eyes makes his heartbeat ever so slightly faster and Oliver knows that even though he’s terrified, this is the best decision he’s made in a while.
“Thank you, it’s… it’s been an adjustment,” He explains with a slow exhale, looking up sharply at Felicity’s chuckle.
“So I’ve heard. Oliver Queen, CEO, who would’ve thought?” She grins, that familiar twinkle in her eye calming him. No one has dared to joke with him since the car crash and there’s something about Felicity’s easy humor that sets him at ease. It’s been so long but Oliver finds himself right back where they were three years ago, in that restaurant for that first date.
“Not me, that’s for sure.”
“You’re not totally hating it, are you? I know the thought of it was your worst nightmare at one point,” Her expression softens a little as she regards him and Oliver swallows, shaking his head.
“Any work at all was my worst nightmare at one point. If I’m going to do something, I’m glad it’s continuing on what my parents spent so long building, bringing it in line with what I know the world to be now,” He explains, a small smile spreading across his face as he does. It matches the one on Felicity’s face and he finds himself excited to talk about this with her. He really does think that he can find purpose in his parents’ legacy, he just has to make it his own.
“I’m glad, I think you’ll do amazingly. You were always great when you put your mind to something,” Felicity reassures him and Oliver is surprised at how much those words mean to him coming from her.
A moment of awkward silence passes between them and Oliver takes a deep breath, looking down at the cappuccino in front of him. He wants so desperately for Felicity to understand but he doesn’t know where to even start going about explaining things.
Luckily for him, Felicity’s always been a little quicker on the uptake than him.
“Oliver, I have to admit to being a little confused,” She tells him, her expression growing seriously as she drops her coffee cup back down to the table. Oliver swallows thickly, nodding his head. He thinks about how he would’ve felt receiving a text from her after three years… he knows it would’ve totally thrown him for a loop.
“I know, I… like I said in my text, I’ve been thinking a lot about the past recently. Don’t get me wrong, I am so grateful for all of the privileges I have been given but I was… a dick to put it simply. Especially our last go of it. You were doing everything you could to build your career and I was… well partying,” He winces as he talks. He’s embarrassed by his behavior three years ago, he knows how important Felicity’s career was to her and he treated it like something akin to his partying.
“So that’s why you invited me here, an apology?” Felicity questions, the surprise clear on her face and Oliver shakes his head, knowing that this is his chance. It’s now or never.
“Well that and… I don’t want to push you into something you don’t want but I… I know that we could work, you and I. I truly believe we weren’t ready for each other then, really I hadn’t matured enough to deserve you, but I… I’d like another chance to try.”
He watches her reaction carefully as he talks, his heart hammering loudly in his chest as he shoots his shot. Her expression morphs into shock as she looks at him before she bites her lip, the nerves evident on her face.
“And if we fall apart again like we have every other time?”
“I don’t think we will, I… I really think I could love you, Felicity,” He tells her seriously, despite the way he can feel his hand shaking underneath the table. He has to give this all he’s got, or he’ll lose her like he has every other time before.
“I think I need to think about this, I really cared for you, Oliver, I can’t go through what I did last time again,” Felicity finally tells him after a long moment, her brow furrowed a little and Oliver nods.
“I understand, take all the time you need, you know where I am,” He tells her carefully. He holds onto the fact that it’s not a straight-out no even as he feels disappointment sink into his bones.
“Okay,” She nods and picks up her bag and coffee cup, leveling him with a small smile before she rises and heads for the door.
Oliver doesn’t watch her go, he can’t. He stares down into his coffee, tracing the lines of the half-destroyed art with a frown. He knows that she deserves all the time she needs but he so desperately wants her answer to be yes that he can’t help the sinking feeling in his chest.
He feels someone appear next to him and looks up, assuming it’s the waitress asking if he’s done. His eyes widen when he sees Felicity stood there, a determined look on her face as she grasps his chin with her hand and pulls him up into a searing kiss. Oliver knows he chokes a little on the air trapped between them but he rights himself, falling happily into the blissful feeling of Felicity’s lips against his own. He’s been dreaming of this for weeks now… years really… and the flying feeling he so deeply remembers is more divine than he could’ve imagined.
“What was that for?” He questions breathlessly as they pull apart and Felicity smiles, wiping lipstick off the corner of his mouth with a single swipe.
“One date, one last chance, Queen, and I expect to be wooed,” She tells her seriously before she spins to walk away once more.
“You got it, Smoak,” Oliver grins, watching her hips sway ever so slightly as she walks away, his heart hammering in his chest as his lips tingle with the memory of her kiss.