Timeline: AU, but I sample canon events
Warning: adult content, coarse language
Thanks to: This would not have happened without renka23's song prompt from ages ago. This may not have been posted without poetgirl925 helping me out. Thank you both!

I brace myself
'Cause I know it's going to hurt
But I like to think at least things can't get any worse

Hurricane Drunk: Florence + the Machine

In the Grip of a Hurricane

She really couldn't believe it as she parked her car in front of her apartment.

Fired.

It really was a banner year for Chloe Sullivan. Her dream job was taken from her, by Lex Luthor no less, but that paled in comparison to her romantic life. A month ago, her relationship with Jimmy fell apart because of Clark, and while Chloe thought she was over him, she decided to do something about it a couple nights ago.

She kissed him. Hard.

But Clark turned her away, just like always, saying he didn't feel the same about her. Chloe knew that, but she hoped there was just a slight chance he would change his mind because her feelings were still there. The stupid butterflies in her stomach, the silly schoolgirl crush, it was still there. And it was never going to happen.

Since that night, she had been giving Clark the cold shoulder at the Daily Planet because she needed time away from him. She couldn't do it anymore and she needed the long brewing feelings to go away. Or at least a distraction, she thought, but getting fired wasn't on her list.

So she turned off her phone, found the sexiest dress she had in her wardrobe, her highest heels and decided to have a night on the town. After all the crap she had gone through, she deserved this.

~0~

Even miles away from his hometown, it seemed like nightclubs were all the same. Every couple of minutes, Oliver thought about shooing away the girls at his side, but after the results of today, feeling wanted felt good for a change.

He couldn't care less about any of their names and that didn't matter because he wasn't going home with any of them. His flight out of Metropolis was in a couple of days and he didn't intend on finding something to keep him here.

Excusing himself from his table, he approached the bartender, who was keeping up with at least ten other drink orders. Oliver manoeuvred his way through the crowd to voice his scotch order, hoping that his name would work in his favour, and it seemed to work as the bartender nodded in his direction.

Seconds later, he started pouring the glass and placed it close to Oliver, so he reached out to grab it, but a small hand snagged it first. Money came on the table not long after and before Oliver could even say anything, he noticed a petite blonde leaving the counter. Looking at the bartender momentarily, he just shrugged and took the money. He grabbed another glass and passed it to Oliver, but he had already begun to walk away, trying to figure out to where the blonde was sitting.

Finally spotting her across the room at a table by herself, Oliver felt his stare linger. The orange dress she was wearing seemed to leave very little to the imagination and the length allowed her legs to be showed off. They seemed to go for miles, impressive considering she had to be at least half a foot shorter than him, even with the silver stilettos that gave her a couple of inches. However, for a dress that seemed to command attention, the woman seemed to be focused on the drink in front of her, dictated through her unwavering distant expression.

About half-way there, he noticed a guy sit at the table across from her, so Oliver thought about turning around, but the guy left just as fast as he came. Oliver began to wonder what he was doing, approaching her like this, as there was a chance there could be someone in her life, but he kept going.

Standing by her table, Oliver was about to introduce himself, but she beat him to speaking. "Flash your smile, cliché, whatever." Throwing back the rest of the scotch, she hammered the glass against the table before looking up at him. "I'm not interested."

Blinking once, Chloe recognized her visitor this time and she only wished that she had one more sip of the scotch. She had no idea what he was doing here, let alone, why he was standing there. Sure, she stole his drink order, but the man could afford to spend more than one minute ordering a drink and honestly, that gesture shouldn't remotely leave an impression. But Chloe seemed to be wrong because he hadn't moved, even after she thought she had made herself clear.

Instead, Oliver turned to lean his back against the table, looking out towards the crowd. "Long day?" After all, scotch wasn't made to be shot down like she had just done.

Chloe scoffed as she pulled back her seat. "Like you care." Feeling her feet hit the ground, Chloe was ready to get out. Nothing was helping and the last thing she needed was to talk to another entitled billionaire.

Oliver let a chuckle out, watching her take a couple of steps before he cut off her path. "Actually, you're quite intriguing."

Her eyebrows raised at his words, as there was no menace behind them, just genuine curiosity. But she shook it aside and walked around him easily. "Right."

Unfortunately for her, Chloe didn't get too far before she found herself walking into someone else. "Hey gorgeous, guy bothering you?"

She wanted to immediately roll her eyes, but Chloe held it back, offering him a fleeting smile. "Sorry bud, not the girl in distress." The guy opened his mouth, so her gaze turned into a glare, causing the guy's eyes to widen and he left quickly.

Feeling proud that actually worked, Chloe stepped forward, but again, Oliver's words stopped her. "Well, I didn't expect that."

The guy had a point, but Chloe had learned anything, it was that she always had to fight her own battles. "If you cross the line, I can sue you for millions." Still facing away from him, Chloe smirked. "That guy... probably 20 bucks." Based on the greasy haircut and sloppy suit, that seemed to be the case.

"True," Oliver said, even though he knew this woman didn't want his money or him for that matter, any more than the guy she just dismissed. The fact she kept walking solidified that. But she didn't leave the place, instead settling in front of the bartender again for a refill.

Chloe thought about leaving, but she knew Lois would likely be at her apartment, and Chloe couldn't face her right now. As sad as this was to admit to herself, a club like this was the only place she'd be safe from Clark and Lois looking for her. For now, all she wanted was space, but it seemed that someone else wasn't getting that message.

Swirling the drink in her hand, Chloe shook her head. "So what can I do for you, Mr. Queen?" At this point, she hoped that she could eventually turn him down like the other guy and he'd leave her alone.

Oliver raised his finger for the bartender to order himself a drink. "For starters, you can level the playing field."

"Sorry," she replied insincerely, "I'm not telling you my name." The question of why he wanted to know her name was definitely on her mind, but Chloe held her tongue.

The remark Oliver expected, considering her hard-to-get nature, but he kept pressing. "Any name then."

Chloe put her drink down and glared at him. The idea of having a conversation of Oliver Queen would have been unimaginable before she arrived, but she had to admit, this was the most fun she had all night. "And then what?"

It wasn't like she was interested in what followed; it was more curiosity coming into play. Just how far was an infamous playboy willing to go to maintain her attention... especially considering her lack of appeal to anyone in Metropolis?

Oliver pointed to her glass, "I can tell you that the stuff you were drinking is not strong enough for what you want it to do." Being around her now, Oliver could see that tonight wasn't about the company, the dress; it was about drinking. Whoever she was, bad didn't even begin to cover what was going on in her head.

Which is why it pained Chloe to think that Oliver was right. A couple scotches down and she didn't feel anything other than lousy. So she peered in his direction to ask, "You have a better solution?"

Downing the rest of his own scotch, Oliver hid his distaste with a smile after feeling the low-quality crap go down his throat. However, such is the risk when he visited places like this and had been exposed to better stuff. And even though Oliver knew this wasn't about him, he knew she would never go with him anywhere. "None that you'll agree to."

Smart man, Chloe thought. But tonight was different. Normally, this dress would still be collecting dust, she would have been drinking at home and she definitely not be drinking with Oliver Queen. So she figured... what the hell. "Try me," she said quietly, seeing Oliver's eyes widen, causing Chloe to laugh in consequence. When no response came, Chloe took another drink. "You've got ten seconds Queen."

He let a couple seconds go by to pick his words carefully, not expecting to even have this chance. Sure, his reputation with the ladies was solid, but even that had limits. So he stuck to the simplest explanation. "Better scotch, no migraine-inducing music and better company?"

"Seriously? That's the line you use to pick up women." Chloe rolled her eyes as she looked around, but she froze as she stared across the club. You have got to be kidding me, she thought as she couldn't believe her luck tonight. So before she had a chance to think about it, she blurted, "Fine."

It was Oliver's turn to blink in confusion. "Excuse me?"

"You want to get out of here?" Chloe asked, pulling her stool out, knowing she had to move fast. "So do I."

~0~

Minutes later, the elevator that would lead to Oliver's penthouse shut and it was just them.

Chloe felt her breathing increase right away, expecting him to make a move, to do... something. But he just stood there, so she felt a little confused. Weren't playboys supposed to be handsy or at least a little possessive? His words matched the reputation, but his nonverbal spoke much louder than words.

However, Chloe eventually shook that aside. Maybe he made his move once they were inside the penthouse.

As the elevator opened, Chloe entered first, looking around as she slipped off her heels, grateful to feel the cool floor against them. "So this is how the one per cent lives."

Taking an extra second in the elevator, Oliver checked her out from behind, almost ignoring her words. "I guess," he replied, finally walking towards his liquor collection in the main area. As he poured the scotch into the glasses, he found himself staring as she smoothly pulled off her coat, laying it near the elevator.

When he looked back, Oliver noticed that he had poured a little much in the second glass, so he took a long sip, evening out the two. Satisfied, he walked over to her, handing her the untouched glass, "As promised."

Chloe took the glass with a slight nod, but she had noticed the drink he had taken earlier. All these little things, she wanted to ignore them, but they didn't add up. "You really are nothing like you're portrayed are you?"

Oliver's eyes narrowed, not sure what gave her that impression. "Really?"

"Game is solid, the smile's a nice touch." Chloe smiled back, but it faded fast as she looked back over to where Oliver was pouring the drinks. But she didn't mean to blurt, "You don't want anyone to know how miserable you are," even if she meant it.

Initially, Oliver thought it was a line of some sort, but watching her react to her own words, he realized that she was indeed serious. So he tried to correct, "I'm not miserable."

Chloe scoffed, deciding to run with it now that it had been said. "Please don't take this as me giving you permission... but I'm pretty sure an infamous playboy would attempt to have me undressed in the elevator." She knew her own sex life was slim to none these days, or any day, but she couldn't shake the feeling that there was more to their encounter than she initially thought. "So why the persistence in the offer?"

Their eye contact locking, silence filled the air for a few seconds. Oliver broke it as he took a couple of calculated paces towards her. "I don't know, but you were pretty persistent about getting out of there. Or did that have anything to do with that guy?"

Oliver wasn't an idiot; after she took his offer he looked around and noticed someone who seemed incredibly out of place. Stood out like a sore thumb, the poor guy. He looked familiar, even though Oliver couldn't place him, but it was clear she knew him.

Chloe's mouth gaped open, surprised he had noticed the tiny slip on her face, but she maintained her cool. "Piece of advice, don't try to justify your victory... relish it instead because normally I wouldn't have accepted." Taking a step back, she turned her back to him, walking towards the couch to have a seat.

There was no way in hell they were getting into that discussion because Chloe didn't want to dwell on it anymore. Finally taking a sip, Chloe could see what Oliver meant as the alcohol soothed her throat. "Although I do have to say, the scotch was worth the trip."

He had watched her walk away, continued to stare as she rotated the glass in her hand. Eventually, he took his own sip. "Thank you."

"So what brings the great Oliver Queen to our side of the country?" They could take the girl away from journalism, but journalistic tendencies would always be in Chloe's heart, even in times like this. It was also the easiest way to avoid the Clark conversation.

Giving her a shrug, Oliver said calmly, "Something that didn't work out." It was more like something that he saw coming, but it had to be done.

"See?" Chloe said, pointing at him, at the look on his face. "Miserable." She smirked, although Oliver didn't see it as she got up from the couch faced away from him. Looking out the window, for a minute, her eyes were lost in seeing the entire Metropolis skyline in front of her.

Meanwhile, Oliver could only chuckle at her assessment, for while it wasn't spot on, it was close. Disappointment more covered his current state, but it was mild at best. Furthermore, he had watched her long enough to he wasn't the only one less than content tonight. "I guess it takes one to spot one." She didn't even try to argue with him, as she turned to look at him again. Instead of a defensive remark or a change of conversation, a tilt of her head was her only reaction.

Noticing her glass was almost empty, Oliver figured it was only polite to ask, "Top up?"

Part of Chloe wanted to leave once the glass was finished, but instead, she handed him her glass. "Sure, why not?" One more drink couldn't hurt at this point.

Oliver refilled it, but left his glass behind, walking towards her again. He could see that her eyes were on the glass, even as he passed it to her. But the moment his fingers released it, her green eyes came up, meeting his. Something felt different now, as there was a sudden intensity in her expression, yet at the same time, vulnerability. Leaning towards her just slightly, Oliver noticed that she wasn't backing away.

Putting her glass down carefully, Chloe stepped forward, all the while wondering what was she doing. This wasn't her, she didn't do this. Even if she was pissed at Clark and trying to avoid all signs of romance in her life after her break-up with Jimmy, Chloe never did anything like this.

Yet as her face moved to within inches of his, Chloe realized that she had played it safe her entire life. Playing the nice card. Maybe for once she'd be that girl, the one who threw caution in the wind. After all, tonight wouldn't mean anything to a guy like Oliver.

But that didn't stop him from teasing, "You're making your playboy comment harder to believe." He didn't want to wreck the mood, but the last thing he wanted right now was to misinterpret it.

"Well," Chloe said with a slight sigh, breaking the contact barrier between them, running her hands up his chest, resting them on his shoulders. "I won't be staying for breakfast."

Suddenly, her eyes contained a playful glint, so Oliver moved his hand to cradle the back of her head. "As long as you don't sue me for millions by lunch."

"I can work with that." And with that, Chloe leaned up and kissed him and it didn't take too long for Oliver to kiss her back.

Sera's Scribbles: Okay, I don't usually define dresses, but I decided to make an exception for this fic. Chloe's dress in this chapter is this little number.

I could regret posting this now, but the muse is cooperating and I'm not about to mess with it. That said, you all know what's ahead, and how I worry ridiculously with this stuff... but it's just about done. With any luck, my worry will be for nothing.