Disclaimer: Clearly I don't own Grey's or George O'Malley. I wish. And I don't actually watch Private Practice. Mistakes are mine.

A/n: So I've actually been playing with this idea in my head for a while but never bothered to actually try and write it. Until the other day when I was talking with a friend about non-canon Grey's Anatomy pairings and we were thinking of ways we could see them happening in canon. We got to George/Addison and she said she didn't think that one was believable or possible. I said, "Challenge Accepted." And I'm really procrastinating instead of getting my stuff done tonight, and I'm needing a distraction from crappy things, so you know.

Set sometime season 5, probably during one of the Private Practice crossovers. Enjoy!

It wasn't something they expected or something they even thought they wanted. They had practically nothing in common, and besides, she was way out of of his league...

The bar was beginning to clear little by little as George opted to order another beer. Meredith left with Derek, Cristina left with Owen, Izzie left with Alex and Lexie left with Mark. George was left alone in the booth near the bar, not wanting to go home to his empty place just yet. He sat back and started people-watching a bit.

He watched Addison laughing with Callie and Bailey but when they left, she seemed to deflate a bit, as if there was something she'd been trying not to think about and now that there was no distraction, it had settled heavily on her shoulders again.

She looked up and caught him staring and he quickly look away, trying to fight the slight blush creeping onto his features. He was still pretending not to notice her when she approached his table.

"You alone, O'Malley?" she asked.

"Yes, but uh, I was actually just about to, um..." He trailed off as she took a seat across from him and set her coat and things beside her.

"Do you mind?"

"No, go ahead."

He immediately felt awkward. He and Addison had never exactly been friends, in fact they'd barely spoken aside from medical procedures when she'd still been a doctor at Seattle Grace. She was Satan. The She-Devil who came back to steal Derek away and wreck Meredith, the Wicked Witch who always picked Izzie for her service and taught her hard lessons about being a doctor, the Slut who slept with Alex during a Sex Bet with Mark (it never ceased to amaze and frighten George how easily any single piece of information was circulated through the hospital's very active grapevine) and the Deserter who'd left Seattle Grace for a new job down in LA.

These were not his words, of course. He'd never really had anything against her aside from the obligatory hatred to support his friends (not to mention that fact that she intimidated the crap out of him and she was fantastically gorgeous, but he supposed that last part was most of the reason why his friends hated her or slept with her, depending on the friend in question). Sitting across from her at Joe's late at night, alone, was new and somewhat unnerving.

Somehow he managed to start some small talk, about how LA was, how she liked coming back to Seattle, how her consult case was doing and so on. They ordered more drinks, she asked questions about what he was doing. Slowly, as the night went on, they became more comfortable (or, George did at least - she always looked comfortable and confident, that bit of sadness from before thoroughly gone or hidden). They started telling funny stories and making each other laugh (she had a really lovely laugh that he'd never really heard before), sharing memories and getting a little more personal. Then sometime around last call, when they were both thoroughly inebriated, they got quiet and vulnerable (a very, very dangerous place to be, George knew somewhere in the back of his mind).

"I thought it would be different," she said after a few moments, her words slurring a bit. "I thought... I thought if I moved away, if I started over, I could..." She gave a frustrated sigh. "I thought if I could start new with old friends, then I could get over everything that happened here, move on, find someone new, and leave all the... all the drama and heartache behind."

There it was - that sad, defeated sort of look he'd spotted earlier which she'd managed to mask again until now.

"But I didn't. I didn't get over anything. I didn't escape the drama and heartache. It's a new location, it's new people, but it's somehow the same: I'm still..." She let out a bitter chuckle, her eyes glistening slightly. "I even got a haircut. Made my hair darker and shorter - as if new hair would help, right? I'm still alone, and I still don't... belong. It's like I'm stuck in this... this horrible limbo that I can't get out of. And I'm sick of trying, you know?"

He had the urge to wrap his arms around her but wisely stayed on his side of the table, instead opting to keep his hands busy by drinking some more beer.

"You probably don't even know what I'm talking about," she shook her head in embarrassment, not meeting his eyes. "I get too drunk and I get all rambly and introspective."

It was his turn for a bitter chuckle. He said, "I do, actually. Know what you're talking about, I mean."

She turned her gaze back to him.

It was his turn to be rambly and introspective, as she'd called it. "I have managed to completely lose any woman I have been in love with. With Meredith I knew there was no chance for me, I knew she was not in a good place and I went ahead anyways, and it was a total disaster. With Callie, we moved so far so fast, with me convincing myself I loved her more than I did or that it was the right thing to do - I-I was just trying to run away from my dad's death. And Izzie... I... I gave up. It wasn't as easy as we thought it should be and nobody got us. So I gave up. I just... decided it was too hard so I wasn't going to bother fighting. And then Lexie - I tried so hard to be her friend and not wreck another relationship, but in the process I completely ignored that she liked me. So I wrecked it anyway."

He shook his head and continued, "Not to mention the fact that I was so busy worrying about everybody else that I wasn't worrying about myself and failed my intern exam. So then all my friends move forward and I'm stuck behind them. They wanted to make things the same, but they couldn't - it isn't. And they just... they've all moved on. And I'm left standing in the background." He paused. "It's like I'm..."

"Stuck in a horrible limbo that you can't get out of." she finished sadly.

"Yeah." He sloshed his beer in his glass and then downed the last of it.

She played with the olive in her half-full martini glass and he felt the awkwardness from before creeping back between them. He hadn't meant to ramble like that, telling her (of all people) things he'd never even admitted aloud, let alone told anyone else, before. Especially since they were both pretty drunk. Then again, that's probably why he'd told her and no one else. They didn't know each enough that this would be uncomfortable the next day (she was leaving, wasn't she?) and it was that whole alcohol-loosens-your-tongue thing. Next time he was in the company of a gorgeous doctor he only kind of knew, he'd have to cut way back on the booze consumption, he decided.

"Sorry," he mumbled a few moments later.

"For what?" she offered him a small smile. "It helps to get it out. Besides," she added, waving her hand at him. "It's not like I'm going to tell anyone. I'm leaving tomorrow."

He smiled back. "Even if you did, I have dirt on you now that I could use."

She laughed. "Touche."

They clinked their glasses and got their last round.

They were both much too drunk to drive, but since her hotel was close, he did the gentlemanly thing and walked her to her room. From there he'd call a cab for himself.

At her door, she swayed on the spot and fumbled for her door key. She stopped for a moment and regarded him thoughtfully. "I get it, you know. I get what they all see in you."

He laughed. "Well, you are very drunk. Sounds like you've got some good beer goggles on. 'Cept you weren't even drinking beer, but you know what I mean - "

"No, I'm serious, I really do. See it, I mean. Not the beer goggles thing. And you'll find somebody, George. Seriously, it's not coincidence that the hottest doctors in Seattle have had the hots for you."

He laughed again, and took a few wobbly steps backwards. "Right. Well, I better go get a cab."

"See you."

He turned away and started down the hall and she watched him go for just a moment longer than she probably should've before putting the key in the door. She was just about to shut it behind her when she heard George shout her name. She leaned out to see him run a little unsteadily down the length of the hall back to her.

"I don't get it." He said and she immediately assumed he was talking about her previous comment about seeing what those other women saw in him.

"I mean, she's my friend and I love her, and yeah, I had a pretty heavy crush or-or whatever on her, once. And I know I am a stupid, stupid guy for blowing my chances with Callie and Izzie and Lexie and everything. But seriously - Derek - he - he has to be the stupidest guy out there. He had you - he had you, and you were married and in love and everything. And he lost you. What kind of moron would let you go, would let you, you know, be with his best friend? And I'm not saying you were, you know, right or anything, but he... Derek is a... well, a complete idiot."

His cheeks flushed and he backed away slightly, cursing the night's alcohol consumption yet again, which seemed to have completely removed the filter between his brain and his mouth. He didn't dare imagine what thoughts were running through her head at that moment - stunning, wildly intimidating Addison Montgomery with her amazing green-blue eyes and red, red lips - and tried to mumble out some form of an apology for his insanity.

She grabbed him by the collar and brought his lips slamming against hers. They tumbled into the room, him kicking the door shut behind him with his foot.

It wasn't something they expected or something they even thought they wanted. They had practically nothing in common, and besides, she was way out of of his league...

Except after that night, they realized that maybe they had a lot more in common than they thought.

-End-

A/n: Well, I think it's a fun idea, if never going to happen. ;) I'd personally be all over George and never let him go! Haha! Anyways, thanks so much for reading and reviews are love. :D