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illicit affairs

Summary:

Oliver Queen and Felicity Smoak do not plan on falling in love with each other. In fact, they deny it at every stolen glance, every instinctive thought, every unspoken desire. But some things are too powerful to ignore. They’re both on separate paths when they meet, but the way they’re drawn to each other is unlike anything they’ve ever felt. If only life could be so simple.

Notes:

One of my favorite things about folklore and evermore is the description of complex characters who make these disastrous decisions and have these messy relationships. I like the idea of my favorite characters making some morally gray choices and not always doing the "right" thing. I think mistakes, big or small, are just a real life truth. I'm interested in characters and stories that reflect it.
In this story, Oliver and Felicity get entangled with each other while they're already tied to other people. Personally I think that circumstances matter in things like this (I don't want to spoil too much of what happens) but if this could potentially be a situation that will bother you, I'd kindly ask that you skip this fic rather than letting it upset you. I will also say that I don't see Oliver and Felicity having such a sad, doomed relationship as the one I see for the characters in the song this fic is named after. Remember, happy endings only for our OTP ;)

(See the end of the work for more notes.)

Chapter 1: clandestine meetings (part 1)

Summary:

On a night when he would rather be anywhere else, Oliver meets a girl in a red dress…

Chapter Text

It's born from just one single glance
But it dies, and it dies, and it dies
A million little times

 

***

Their winter home in the Rockies, teaching Thea how to ski.

Getting lost in the streets of Tijuana with Tommy.

A beach in Aruba.

Hell, even going back to Yale.

There were a million places that Oliver would rather be.

Instead, he was sitting in a restaurant in Starling. The city he loved. It was where he’d grown up, found himself, and decided to stay. It was a comfort. It was a home. But this dinner? This dinner was so far from where he wanted to be tonight. His leg was bouncing beneath the table with each second that passed, itching to get up and run out the door.

His mother had called earlier that afternoon and invited him to dinner. And since he’d been so busy lately; ignoring calls, cancelling plans, and overall being a pretty crappy son, it wasn’t hard for a little guilt trip from Moira to go a long way. It got him to finally sit still for this dinner, at least. The problem was, of course, that his mother couldn’t miss an opportunity to meddle in his life.

Without his knowledge, she’d invited Helena Bertinelli along. And despite the fact that they were so hot and cold it gave him whiplash, Helena had apparently agreed. Her parents were friends with his parents. They crossed paths a lot. And at first, it was mutually convenient and they kept it simple. 

Lately though, Helena was becoming less of a mutual convenience and more of a headache. He noticed that she called more. Wanted to see him more. Not that he minded that part...but he wasn’t sure when they’d gone from casual hookups, to dinners with his mother. If her parents had called him and invited him out to dinner, he sure as hell wouldn’t have accepted the invitation. Or he would have at least warned Helena about it. But she hadn’t said a word, leaving him blindsided when he showed up for a meal that he thought was just going to be him and his mom.

It was weird, to say the least.

Of course, Moira being Moira, she didn’t waste much time. Once they got past the initial surprise and awkwardness, she didn’t hesitate to start grilling them about their relationship status and where they thought things were going. He knew his mom was perceptive and he assumed she’d heard rumors or even seen him talking to Helena at events. 

Moira Queen always had an agenda.

To his chagrin, Helena insisted on answering each of Moira’s entirely invasive questions. When he tried to brush her off and politely say that it wasn’t any of her damn business, Helena shook her head and gave a coy answer of, ‘we’re still figuring things out.’

And Oliver was reeling.

What the hell did that even mean?

What the hell was happening?

As far as he was concerned, there was nothing to figure out. Nothing to discuss. It was simple. They had an attraction, good chemistry, and good sex. He had never given her a reason to think that he wanted anything more out of this than that. In fact, he’d been quite clear about it. And he thought Helena was on the same page. Wanted the same thing. Which was nothing more than sex whenever it suited them.

So, while Moira and Helena sipped wine, laughing and bonding over stories of his childhood, Oliver stewed. 

He thought about all of the places he would much rather be. Moira had just finished telling Helena how jealous Oliver was of Thea when she was first brought home from the hospital and took up all of his parents’ time and attention, when she suddenly shifted the conversation. “So, darling,” her eyes zeroed in on Helena, “do you want children someday?”

Oliver froze. 

Helena’s cheeks flushed pink and her eyes met his, but then she turned to smile at his mother. “I do,” she answered confidently, like a pageant queen on stage, trying to appease the judge. “I’d love at least three or four.”

Moira smiled back, nodding in approval at that answer. “A house full of children is a house full of love.”

More like…a house full of children was a house full of distractions, if his childhood was any indication.

If he couldn’t get to the Rockies, or Mexico, or Aruba, maybe he could just take his salad fork and stab himself? Surely, a trip to the hospital would be more enjoyable than this conversation.

As if in response to his violent thoughts, or at his pathetic expense, the table across the restaurant erupted with laughter, voices carrying across the room. 

Oliver glanced up at them, much more interested in their fun than he would’ve been if he didn’t hate everything about his life at that moment. 

It was a large table of men and women, clearly celebrating one of the guys seated in the middle of the table. He looked embarrassed as they all cheered for him, patting him on the shoulder and clapping. Every single one of them screamed cop to Oliver as soon as he noticed them. He’d had enough run-ins with the law when he was a teenager to recognize the type.

After a few moments of observing them, they all started to move back to their seats, bringing their drinks with them as they gave some space to the man at the center of the attention. 

It was only once their little crowd parted that Oliver noticed the woman sitting beside the man. She stood out. Even if she hadn’t been surrounded by bland, ill-fitted suits and bad haircuts, she would have caught his eye. 

Most women who were as gorgeous as this one usually did.

She was wearing a red dress, and Oliver couldn’t help but wonder if she’d done it on purpose; a splash of color in the rather dull group. Even from his spot, he could tell how blue her eyes were. He could also tell that she didn’t quite fit in with the others around her. While the people at her table (probably cops) were conditioned to blend in, she seemed like her intrinsic nature was to stand out.

The woman smiled and held her wine glass up when the others at the table offered theirs in cheers. But she didn’t seem like she was one of them (not cop-like). Just a tense, beautiful woman sitting in the middle of some rowdy, obnoxious chaos.

“Helloooo, earth to Oliver!” Helena’s fingers snapped in front of his face, bringing him back to his own dull world that he’d been all too happy to tune out for that moment.

Prying his eyes away from the stranger, he did his best to at least follow the conversation between Helena and Moira. They’d circled back to the seriousness of Oliver and Helena’s relationship...which Helena seemed perfectly willing to entertain. Oliver wasn’t quite sure if she was just trying to appease his mother, or if he had truly misled her enough that she believed they were, in her words, ‘on the right path in their relationship.’ But either way, it was a joke. And it was stressing him the fuck out that his mom and his casual hook-up were talking like this. 

Still, he didn’t want to cause a scene or embarrass Helena, so he clenched his jaw and kept quiet. 

They just needed to get through this dinner. Then he could have an honest conversation with Helena, in private, about where they were, or rather were not going in their ‘relationship.’

Helena and Moira certainly weren’t making it easy for him, though.

His saving grace was the girl in the red dress.

He found himself looking over to her again and again; every time their table’s excitement disturbed the restaurant or every time Helena and Moira’s conversation disturbed him. And both of those things happened quite a lot throughout the night.

It almost became like a game.

Oliver would look at the girl, using her as a distraction, letting himself wonder about her. Each time he did it, he would silently hope that she would look over at him.

It was just a dumb distraction, but he imagined that the woman’s eyes would meet his, and she’d feel whatever this bizarre, instant attraction was that he was feeling. Maybe he’d smile at her. Maybe she’d give him some kind of hint that she liked what she saw, too. So he’d go over and get her number.

And then he would take her home. 

Surely, that would put to rest this whole Helena mess. No better way to send the ‘I’m not interested’ signal like picking up another girl right in front of her.

It was very in line with his old habits. Oliver liked to think he was better than that now.

No, he knew he was better than that. He had to be.

But obviously, he had made a mistake with Helena.

In the back of his mind, Oliver knew that the answer was simple. Just tell them. Tell Helena that you’re sorry if you led her on, but this isn’t going to work anymore. Tell Moira that it was entirely inappropriate to pull something like this. Go home. And move on.

“Oliver!” His head snapped up as his mother stared at him across the table. “I said, ‘how are the campaign preparations going?’” She shook her head at him, a slight smile on her perplexed face. “What on earth has gotten into you tonight?”

He cleared his throat, “It’s going well. I’ve been advised that there will be...obstacles, um, given my past. But I have a good team behind me. We’re prepared to announce my candidacy in a few months.”

Moira pursed her lips, glancing between him and Helena.

Uh oh. 

Here it comes.

“Darling, that’s actually why I wanted to talk with you both tonight.”

Oliver cocked his head to the side, looking to Helena first, seeing that she was just as lost, and then back to his mom. “Helena hasn’t had anything to do with my mayoral campaign, mom.”

“Oh, but she has, Oliver,” Moira countered. She leaned closer, lowering her voice. “You’re planning to run for mayor. How do you think it looks to the leaders in this city to see you ducking out of social events early with Miss Bertinelli under your arm?”

He sucked in a breath, thrown off guard. It had been quite a while since his mother hit his ego like that. “I think it looks like everyone else needs to mind their own business.”

Moira shook her head, giving him the ‘mom’ look that she had mastered after all these years, raising a heathen for a son. But it was different now. 

“You know better than that,” she pointed out. “We both know that that is not how things work. Listen, I am sorry that you grew up with such a spotlight on you. But if you want this city to see you as a man who can be responsible, then you need to stop acting like the boy that they remember you as.”

She sure did know how to throw low blows with her words. 

“Mrs. Queen,” Helena finally cut in. “It was never my intention to threaten Oliver’s chances to be mayor. I mean, the election hasn’t even started yet, we...we didn’t really think about it.”

Moira’s eyes flickered to Helena, “I know, which is a problem, Miss Bertinelli.” And then she sighed, “But not entirely your problem. My son should be the one more concerned. More cognizant of how his actions will impact his future.”

“I’m sorry,” Helena shook her head. “We’ll be more discreet.”

He closed his eyes, a sinking feeling in his gut because after the night they’d been having and a lifetime of Moira Queen’s tricks, he already had an idea about where she was going with this. She wouldn’t have called them to dinner and gone through all of this trouble if she just wanted to warn him to be more discreet about his sex life.

“I don’t think discretion is the answer, dear. Secrets always have a way of being uncovered.”

“Mom…”

“What I’m saying,” she ignored him, “is that it’s time you two get more serious about each other.” She looked to Oliver for a reaction. He gave her none. “The people in this city want a mayor that they can trust. I believe that the best way to do that is to let them see you as a faithful, committed man when it comes to your personal life.”

“You think that I would seem more trustworthy…if I lie to them?”

“What’s the lie?” Moira waved him off. “You have a beautiful, intelligent, kind woman right in front of you. You two have practically been dating for six months now, if I have it right. I think that you should just…consider a future together. Consider marriage. And children. And all of the things that people usually hope for in life. The things that people will relate to, Oliver. If you want to be mayor, they will want to see you as a stable, reliable, honest man. It’s not just about the work you’d do for the city. They’ll need to trust that that is who you are. Professionally and personally.”

She was unbelievable.

“And if the campaign ends and you two decide it isn’t meant to be…” Moira continued, lifting her hands innocently, “then so be it.”

The table fell uncomfortably silent as Oliver and Helena both processed what Moira was suggesting.

A relationship for the sake of his campaign. Designed for his campaign. Because there was no way that his mother actually believed he could see himself with Helena. He didn’t believe that Moira could see that future for him, either. Yet she’d spent all night entertaining Helena. Because she was leading up to this.

His mom was diabolical.

And even though his gut reaction was to tell her that it was an insane, risky, unnecessary plan...he didn’t. 

Moira had hit the nail on the head. He wanted to be mayor. Badly. And his biggest fear was that people would laugh at the idea because they would always see him as a young, dumb, arrogant jerk of a kid. Always causing a scene. Always in the tabloids.

It had been a long time since he’d been that kid. But the future of his campaign truly hinged on whether or not people could forget all of that and see him for who he is now.

What if they couldn’t?

As crazy as it seemed, Moira’s suggestion could help dictate that narrative. Paint him as a responsible adult who had settled down and fallen in love. It would show everyone that he could be serious about this job. That he could commit to the work and dedication it would take. Because in his personal life, he had grown up.

He hated it, but Moira had a point.

“It’s just an idea,” his mother murmured, a look in her eyes like she knew she’d gotten through to him. “A way to make people respect you and listen to what you have to say rather than writing you off. No one will care if you split up by the end of the year. By then, they’ll believe in you .” his mother continued, persuading him. “As long as you and Helena are on the same page publicly and privately, I don’t see the harm in it.”

She didn’t know Helena. He could see plenty of harm.

“I’ll think about it,” Oliver said instead.

Moira held his gaze, trying to decipher if he was actually listening, or just appeasing her. And truthfully, he wasn’t even sure himself which one it was. 

Of course, there was one other person in this equation who needed to be considered. Oliver looked at Helena, “And what do you think of all this?”

“I think…” she let out a sharp breath, “that a lie is a lie.” Helena lifted her chin, as if in challenge. Disagreeing with Moira Queen was nearly impossible. It was an intimidating thing to do. He himself had just avoided it. But he had to admit, it was attractive that Helena spoke up. “I think it’s taking a risk, and I’m not sure that Oliver’s campaign needs to be taking risks.”

Oliver smirked, like it was some kind of victory that Helena didn’t yield to Moira’s wishes. Yet when he looked at his mom, she had a smile on her face, too. One that Oliver had grown used to. He knew that look. His mother had a plan. And it was going exactly how she wanted it to.

“You believe in him,” Moira said. 

Helena straightened her shoulders, her cheeks flushing as her eyebrows furrowed. “Well...yes. I know how much he wants this. I’ve seen how much he cares about this city.” Her eyes flickered to his, almost embarrassed as she added, “I’d vote for him.”

Somehow, miraculously, Helena’s words warmed him. It was exactly what he needed to hear. Even if the sentiment was simply that she thought he’d be a good mayor, it meant a lot. It was more faith than his own mother was giving him.

“That’s because you’ve had the chance to get to know him,” Moira answered. “And I think you could help the rest of the city do the same.”

Oliver sighed, more conflicted than before. He’d been antsy since the moment he sat down at this table and now his anxiety was climbing with each second he stayed there.

It was as if the plan was already in place. He’d be in a committed, arranged relationship with Helena Bertinelli whether he liked it or not. 

Because Moira Queen didn’t quit until she got her way.

“Excuse me,” he cleared his throat.

Getting up from the table, Oliver managed to calmly walk to the restroom, even though his body was tingling with the urge to run to the nearest exit. Once he was alone in the bathroom, he loosened his tie, looking at himself in the mirror as he took a deep breath. Then another. His face was pale. He was too hot. 

Trapped.

Anxiety crept up from his chest to his throat.

Suffocating.

Just the idea of what his mom suggested was making him feel like this.

Shouldn’t that tell him everything he needed to know?

Oliver splashed some water onto his face, but the feeling wasn’t going away. He had no idea how he was supposed to go back out there and have a calm conversation with his mother and the woman he’d been casually sleeping with about pretending to be in a relationship so that he could win an election. 

It was insane.

Risky, like Helena said.

Needing some fresh air, Oliver opened the window above the sink. He closed his eyes and strained towards the breeze. It provided a moment of calmness that had him practically sticking his head out of the window for more.

And...not knowing much else aside from the fact that he needed out , Oliver found himself climbing onto the counter and then out of the window.

It was a tight squeeze. He scratched himself on the windowpane, and his back immediately hated him for the borderline gymnastics it took to make it through. He instantly regretted the snap decision, but he was already halfway down.

Surely, it wasn’t his finest moment. But once his feet hit the pavement of the alley below, Oliver had to admit that he instantly felt better. 

Free.

“You look like you’ve done that before.”

Spinning on his heel, Oliver’s eyes adjusted to the darkness in the alley, shifting to where the voice had come from.

Oh shit. Oh. Shit.

Girl in the red dress.

Girl in the red dress was standing on the other side of the alley, leaning against the brick wall. She looked like she’d been there for a while, long enough to see his full escape, at least. Her hands were in the pockets of her white coat and she had one eyebrow raised. He knew his face had to be screaming ‘I’ve been caught red handed, and I’m guilty as hell.’ 

“Well, have you?” she asked as he stared at her.

“Have I what?” he blurted.

She pushed off from the wall, narrowing her eyes as she closed the space between them. “Have you snuck out of a bathroom window to run away from a date before?”

Oliver blinked, glancing up at the window he’d just climbed out of. “Oh...I...it wasn’t a date.”

The woman cocked her head to the side, crossing her arms over her chest.

Damn, she was even hotter up close.

“That wasn’t my question.”

He released a breath, watching her for another moment as he tried to figure out the best response. One where he might be able to not look like a total asshole. He could lie, of course. But… “Not exactly,” he said instead. “But, um, yes? I’ve bailed on a date before. Snuck out through the back after she told me she had handcuffs and a blindfold in her purse that she planned to use on me. It was an awful date.”

The girl in the red dress leaned a little closer, her eyes on his face, studying him. “So you left through the bathroom window instead of telling her that you weren’t interested in some light bondage.”

His eyes widened, “Light bond—”

“Isn’t that kind of…” the woman interrupted, tapping her hand against her chin as she narrowed her eyes at him, “cowardly?”

Oliver forced a laugh, tight and uncomfortable. Not off to a great start.

“It was a first date and I barely knew her, let alone trusted her with something like that,” he defended himself. “But no, I’m uh...not great with confrontation,” he waved up at the window he’d just stumbled out of. “Clearly.”

Well, at least that got the girl in the red dress to smile.

“Clearly,” she agreed. “What’s your name? I’d like to at least have some details to give my friends when I tell them this story.”

He huffed out an embarrassed breath, grumbling the answer, “Oliver.”

The woman nodded, already turning to walk away. “What’s yours?” He quickly called after her. He had to know. He’d only spent most of the evening admiring her.

Her smile tipped up a notch as she glanced back at him, “Felicity.”

Felicity.

Of course her name was as beautiful and different as she was. A splash of color.

She started to walk away again, apparently content to leave their encounter at this. 

But Oliver wasn’t as willing. His chances were low...she’d just watched him pathetically fall out of a bathroom window, after all.

On the other hand...what did he have to lose then?

“Hey, Felicity!” he called after her again. 

Yep, her name felt good on his lips.

When she turned back to him, Oliver put on the best, most charming smile he could manage. “Do you want to go get a drink with me?”

In response, she laughed. Actually laughed . His hope dwindled. 

Of course, he couldn’t be surprised that she’d laugh at him. It was probably the worst first impression he’d ever made with a woman.

Which is why it surprised him even more when Felicity lifted her shoulder and offered a simple, “Sure.”