There is some slight timeline skewing in here. Because if the CW can give Chloe birthdays in different seasons, I can shift events by a few weeks. Set in Seasons Eight, Nine, and Ten.
Disclaimer: I do not own the CW, Smallville, Superman, or the characters that reside within the show/comic.
Please note: I fixed a typo. Thanks Angela for pointing out, but consider being more constructive with your criticism, especially if you're not logged in.
Other than that, please enjoy!
Oliver laughed as Chloe tried to reach up and take the tickets from him.
"Where-are-we-going?" she asked, each word punctuated with a jump. Oliver simply held the tickets over her head.
"You'll see when we get there," he replied, secretly enjoying the feeling of her next to him. He grabbed her hand and hauled her out the door, putting the tickets in the pocket farthest from her. Please don't let this end, he thought.
Chloe didn't release his hand, so he held it until they got to the stadium.
Chloe laughed a little. "A baseball game Ollie?"
"You ever been to one?" he said, challenging her.
"Well, no but-"
"Ah, no buts. We're going to go and enjoy ourselves for a few hours. I'll buy you hot dogs."
They cheered for the Metropolis Meteors. Oliver wiped mustard onto Chloe's nose, and she retaliated by smearing ketchup on his cheek; both giggling the entire time. Later, Oliver would realize he had no idea how the game had turned out.
She talked him into getting coffee on the way back. He was incapable of saying no to her, although it was getting late for coffee.
He pointed this out and she replied, "It's never too late for coffee. You should know this, knowing me for so long.
Oliver chuckled and conceded. As they waited in line, he noticed a pair of policemen walking back to the car with coffees in hand.
"Five bucks they're getting donuts next," he whispered to her, swearing a moment later when one pulled a donut out when he closed the door.
"Hand it over," she smirked.
"How about I just pay for your double espresso venti mochachino instead?"
"Sounds like a deal," she said.
As he paid, he wondered if she'd ever stop pretending they were just friends. He was giving her the space and the fun she needed after the disastrous end of her last relationship. At some point though, he'd have to stop waiting.
"I don't want to stop having fun like this," she told him as he returned her to the Watchtower.
"Who says you have to? I'll take you anywhere you want," he grinned.
She smiled back, shaking her head a little. "Ollie, you're cute, but remarkably optimistic. You're taking off again soon, and you have no idea when you'll be back."
"I know," he replied. "I'll just fly you out to me on my jet." On that note, he waved goodbye, both to leave her laughing and to avoid her next excuse.
That night, he remembered what she'd said to him on her birthday, when she was still hurting from Jimmy's departure.
"Ollie, sometimes I think you're the only one who cares about me."
"That's not true," he protested.
She shrugged, dismissing his statement. "Don't ever stop, okay?"
"Okay," he promised, before telling her he had to leave on Arrow business and hating himself for it. He left her alone after just promising to stay. She didn't know he went back to the Ace of Clubs, as well as her apartment later to make sure she made it home alright.
He knew that while much of Jimmy's breakup was a result of Chloe's relationship with Davis, it was equally about the secrets she was hiding. Many of those secrets were his. He felt guilty for playing a part in the demise of their marriage. At the same time he knew that they would never last if Chloe couldn't be honest with Jimmy and she had told Oliver far too many times that Jimmy could never know about the team. It would mean the end of the small slice of normality that she craved so badly. Even with all of her efforts, the relationship, and thus her chance at a normal life, ended.
So, Oliver did his best to cheer Chloe up. He also tried to slowly and subtly adjust her to the idea of being with him. He made no true advances, hid his feelings behind snarky comments and let her do whatever he pleased.
The few months after their breakup consisted of missions filled with flirty banter, some "friend dates" both around the world and in Metropolis, and the occasional night in that often ended in hero duty.
Then came the devastating day of Doomsday's rampage and Jimmy's death. Oliver's guilt over that failure, coupled with Lex's murder, sent him away for months. Chloe brought him back from the very edge. He would never forget it and neither would she. Slowly, the team came back together under her watchful eye, both of them leading now.
Even more slowly, Chloe drifted towards Oliver. When she initiated a simply physical relationship he knew he had to take it. It was either that or walk away from her forever and he was nowhere near capable of doing that. It was difficult for him to keep his feelings hidden now that she was in his bed three nights out of four. He managed somehow though. He had to or he risked scaring her away for good.
He called on a Saturday afternoon several weeks later. "Get your gear ready Sidekick! We've got a night on the town. We're gonna party it up." Although she still refused to accept gifts, she would take dates.
"So you want going out clothes, not take down bad guy clothes?" Chloe was excited. They rarely went out in Metropolis these days.
"Yep. See you at five-thirty." He hung up before she could ask any more questions. He had to keep her on her toes, after all.
Chloe glared at the phone when he hung up. She decided to assume he was taking her to dinner, though what was afterward was anyone's guess. Why did he always pull this last minute? She knew the answer; it was because he knew she'd always say yes.
By five twenty-five, a showered and dressed Chloe was waiting for Oliver to arrive.
"You look great!" he said upon opening the door. Chloe had put on dark jeans and a green top. Part of her realized she was teasing him, to wear his favorite color.
When they got to the club, Chloe turned to him with her megawatt grin. "How'd you find out Lifehouse was my favorite band?"
He put on his open surprise face. "What? You're the only one allowed to know things about other people?"
She just shook her head and grinned again. Inwardly, she was incredibly nervous. This felt more like a date than anything else they had done in the past few weeks, or years for that matter. Not that she could put her finger on why, exactly. They had gone out before, quite often in fact. Still, she was nervous, afraid that he was thinking about leading their relationship out of "friends who happen to like having sex with each other" territory.
Shaking it off, she managed to enjoy the concert immensely. She leaned into Oliver unconsciously when he wrapped an arm around her waist. Oliver, on the other hand, was perfectly conscious of the movement. He was also aware that she fit there perfectly. He knew was hiding his feelings from her and that Chloe was pretending hers didn't exist. It was only when she let her guard down that the truth shone out.
Walking back to his car, they took a detour through the park and Chloe held Oliver's hand tightly.
"Are you afraid of the dark, Sidekick?"
"Just nervous the Green Arrow will appear," she told him mischievously.
When is she going to stop pretending? He wondered. He knew they were no longer just friends with benefits. Hell, the whole team knew it. She was worth waiting for though.
He thought about her birthday, just last week.
"Ollie, you know I love you right"? She'd asked him.
Oliver gulped. "Of course Chlo," he decided was his best response to a drunk Chloe.
"Don't you love me too?"
"I love you very much. You won't remember this in the morning, will you?" he asked apprehensively.
"Noooopppeee!" she sang twirling around the center of his apartment, hands spread. "I don't want this night to end! I'm having soooo much fun!" she fell,
He couldn't help but laugh as he sat next to her and pulled her into his arms. "Me neither," he whispered into her hair.
True to her (rather drunken) word, she didn't remember it in the morning.
She had nearly cried when he returned from Checkmate's clutches. Later, they laughed over how easily he'd escaped. She had teased him for weeks when he finally told her he'd accidently spilled his secret to Tess-after shouting at him for twenty minutes and not speaking to him for three days. He cajoled her back by reminding her of the mistakes Clark had made, and her own as well (very subtly). She was back in his bed that night.
When she was captured by Checkmate, he nearly stormed the castle himself to get her back and came very close to admitting his feeling to her when he saw her that night. He knew she suspected it, and he was beginning to think he might not care.
He had been flirting with her for well over a year. He was playing at being simply friends with benefits to get her closer. Oliver knew Chloe trusted him, but as she had said, she just didn't trust him "that much".
So he began to throw caution to the wind. She had told him she loved him and forgot the next morning on more than one occasion. He suspected he had probably opened up to her on a drunken occasion or two. Whether she had listened or not, he didn't know and wasn't sure he wanted to.
Oliver's birthday had been fairly wild this year. Between the attacks from Checkmate and the nearing Kandorian battles, he felt he'd deserved it. It couldn't be worse than the year before. Chloe wouldn't try anything crazy this time.
And so, after his annual beer pong game with Lois, he had gone out with the team and come back around two, totally smashed. He was wobbly and grinning at her.
"Chloe," he said.
"C'mon Ollie," she giggled. "Let's get you to bed."
"'m sick of this." He said. Chloe paused. "I'm sick of pretending we aren't what we are."
Chloe stared, slightly perplexed. "Oliver, this isn't the time to talk about this."
Yeah, it is," he replied. "Chloe I really care about-"
"Stop," she cut him off. "We aren't going to talk about this."
"Fine," he said. "Just promise me this won't end."
"I promise," she murmured as she walked him to bed.
Then came the day they had all been fated to die, just two weeks later. In those moments before he was fully surrounded he gave up and told her the truth she'd been ignoring.
"Chloe, I love you," he'd said, and one time-stopping, forever-lasting second later he heard her strained, panicked voice reply, "I love you."
That was the last thing he thought before he realized that he wasn't facing Kandorians. Then there was no thought left.
Months later, he got her back. She held him so tightly he thought she would never let go. Not that he wanted her to. He wasn't going to let it end this time. Finally she loosened her hold. He could feel her breathing in his scent, a gesture that comforted and calmed both.
Eventually, they settled into something resembling a routine.
They would go out some nights, and stay in others. Those nights, they would watch movies or play video games or just sit and reminisce. Chloe and Oliver were equally good at teasing each other.
One night, Oliver stopped talking and just started looking at Chloe. In the middle of a story, she didn't notice for several moments.
"Promise me," he started, when she glanced at him. They were sitting outside on a picnic blanket, staring at the stars.
"Don't let this end," she finished.
She looked at him, eyes bright and lips slightly parted. Then she said the words he'd been waiting for.
"I love you," it was so soft he hardly heard it. But still, she'd said it first and that had never happened.
"I love you too," equally softly. Then he leaned down and kissed her gently, far more sweetly than they typically kissed. When she returned the kiss and pulled his head closer he knew what they had would never end.
I really enjoyed writing this. The inspiration came from a song with the same title.