A/N: So, after watching Roulette, I had a strong urge to write a Chloe/Oliver story, but I didn't get a chance to. Now, after watching Crossfire tonight, I couldn't resist. So, here goes, my first shot at the Chollie fandom. This takes place right after Crossfire. Hope you enjoy! Please R&R! Thanks!

Disclaimer: I do not own any of the characters.

Taking the Right Risks

Oliver stared blankly at the TV screen hanging above the bar, the only form of entertainment his venue choice provided. Some hockey game was playing, but he was oblivious to it. That's because there was something else playing inside of his head, that night's events to be exact. And, to be even more precise, the moment he had risked his heart to the woman he once loved and thought still did.

To be perfectly honest, risk would be too strong of a word. Actually, it was more of a lie. That's because Oliver knew that trying to get back together with Lois was more of a safe choice than a long-shot risk. He knew Lois; he knew every good little thing about her, like how she was fiercely loyal to her friends, as she proved tonight. He also knew, despite what he had told her, every annoying fact about her, like how sometimes you couldn't get her to shut up.

Oliver knew they were good together, because they had done it before. She was safe, and God knew he needed to make some safe choices in his life from now on. But that was not to be.

He wasn't surprised when she'd shot him down. Of course, they had had their reasons for breaking up. He was still the Green Arrow, despite his temporary leave of sanity. And the news that Lois wanted Clark wasn't a shocker either, he had suspected as much ever since the disastrous night of Chloe's wedding to Jimmy.

Speaking of Chloe… Oliver's mind got completely sidetracked at the mere glimmer of a thought of Chloe. His face completely lit up and anyone who was watching him would think him the happiest man on earth.

Now, when you talk about taking risks, Chloe took one hell of a chance on him. One that he would be eternally grateful for. She had literally saved his life. He shuddered to think where he would be if she hadn't intervened in his life. Face down in a gutter, in front of a sleazy bar, that was for sure.

Speaking of sleazy bars… he wasn't quite sure why he had picked one when he had first decided he needed a place to contemplate that night's festivities. He guessed old habits died hard.

Letting out a calming sigh, he reached into his jacket and pulled out a few bills, tossing them onto the counter. It was time to put what was already done behind him.

Before standing up a slim hand came into his view, putting down a drink in front of him. It was followed by a voice saying, "After the night you've had, I don't think one more drink is going to kill you."

Oliver looked to his right, seeing that the long, slim hand belonged to a dear friend, one he was just thinking about.

"Chloe?" he said in surprise.

"Don't get me wrong, I'm not going to be your enabler or anything. But I know all about unrequited love and it sucks big time," Chloe half scolded, half soothed. "I heard about what happened tonight."

Oliver nodded, turning back around, unsure of what to make of Chloe's sudden appearance. "Are you following me?"

Chloe laughed heartily at that. A sound that sent tingles down Oliver's spine. She pulled the drink away and said, "Ok, maybe no more drinks for you anymore. I think the paranoia has set in."

He gave her a sidelong quizzical look. She hadn't really answered his question. But he guessed he really didn't mind having her there.

"Mia all set up with the team?" Oliver asked instead.

Chloe nodded. "Yep, Bart picked her up and she was gone in a flash. They'll begin her initial training and let you know when you can take over."

"Thanks for arranging that, Chloe," Oliver praised, sending his Watchtower a warm smile. "You're the best."

She smiled back, staring at him shyly from beneath her lashes. "That's what I'm here for. It's my job."

He turned to face her fully, considering her carefully. "Is it also your job to be a certain dumbass billionaire's saviour and hero?"

Oliver had her blushing instantly at that. In all the time he had known her he had thought her one of the few women immune to his charms. He believed that was one of the reasons they had become friends so easily. Also, one of the reasons why they could tell each other when their crap was getting in the way of life. But, it seemed, he could have an affect on the lovely blonde.

"How're you doing after tonight?" she asked instead, ignoring his question.

Once again he turned in his chair to face the TV screen over the bar.

"I'm fine, just a few bruises. I'm just glad Clark was there in time to catch that bullet, or else I would have been toast," Oliver answered quietly, so as not to let anyone else hear.

"No, I don't mean that. I mean, I'm glad too, but I mean the other risk that you took tonight, other than coming between Lois and a bullet," Chloe countered.

"She told you, already?" Oliver scoffed.

Chloe gave him a wry look. "It's Lois, Oliver. She's not one for the not talking, you know? Besides, I'm her cousin, we tell each other everything."

"Everything?" Oliver drew out suggestively.

Chloe laughed, giving his arm a playful push. "Eww Oliver, no, not everything."

Oliver joined in on her laughing, enjoying the simple human interaction. When the moment died down it was quiet, but not an uncomfortable quiet. It felt nice to just sit with someone with no expectations to say anything.

He glanced down quickly when he felt Chloe's hand cover his own. He stared down at their joined hands for a good minute, before meeting her green-eyed gaze with his blue one.

"But, seriously Oliver, are you ok?" Chloe asked genuinely.

She was concerned for him. Chloe had invested a lot in him to get him back. And he could tell by how worried she suddenly was that it wasn't just because she had wanted the Green Arrow back. She cared about him, he suddenly realized.

Slowly, his face broke out into a grin. And he could tell that Chloe was instantly confused by it. But he couldn't help it. He knew he had taken the wrong risk tonight.

"I am completely fine," he told her truthfully.

"But… but, Lois turned you down tonight, for Clark," Chloe said, not bothering to hide her confusion.

"Ah… but you see, I had it all wrong. I thought I was being all risky, taking a chance on Lois. But, I realized I was actually trying to play thinks safe for once. Who can blame me, right?" he spoke quickly. "Lois is the safe choice. I wasn't taking a chance at all. I wasn't taking the right risk."

"Ok," Chloe said dumbly. "What is the right risk?"

Oliver's grin broadened further with her question. "She's sitting right in front of me."

He waited until realization dawned on Chloe's face, for her to know that he meant her. That he wanted a chance with her. He waited until he noticed the exact moment she formulated a response and was ready to give it to cut her off with the touch of his lips to hers.

He had completely shocked her, if her just sitting there was any indication. But when his hand went up to gently touch her face he felt her sigh before she began to kiss him back. In fact, her arms slid behind his neck of their own free will, with no coaxing on his part. And he took it as incentive to use his free hand to wrap it around her waist and pull her closer. The kiss lasted a good two minutes when he finally felt he needed to give her time to process.

Oliver pulled back slightly; their faces still only millimetres apart, to see Chloe's eyes still closed. He smiled warmly to see she was still caught up in the moment. He leaned back further and cleared his throat.

Chloe blinked a couple of times coming out of her trance, she put a hard look on her face; one that Oliver couldn't help grinning at. It was too hard for him to match her seriousness when he knew she had enjoyed that kiss as much as he did.

"What," she began tersely, "was that for?"

"Come on Chloe, I know your hearing is fine. I told you before; you're the chance I want to take. I'm hoping you'd like to take another chance on me too."

She considered his words, giving him a shrewd stare before saying, "I'm not a Lois substitute. I'm nothing like her."

He held up his hands in protest. "I know that. You're not Lois, you're my own personal hero and I'd like to show you how much that means to me."

The hard stare melted away to be replaced with a soft smile. "How much?" she asked quietly.

Oliver took Chloe's hand in his and stood up. "More than you know Chloe. It would take me forever to show you."

Chloe smiled brightly. "Lucky for you, I'll be around."

Oliver nodded. "Lucky for me, is right."

Well, I hope you enjoyed this little one-shot. I'm new to the Chlollie pairing, but I think I'd like to see a little more than a hint of it in the show.

Anyways, leave me review and let me know what you think. Thanks!