So I found this little guy on my computer while looking for another partially started DB fic, and I decided, what the hell! I have insane writer's block right now so might as well write some bad fanfiction to procrastinate! This is a '5 Times' story. I've never written one of those, but here's the setup/prologue.

p.s. It's a little AU because I wrote this like last year so season 4 is null and void. Also reviews will encourage me to actually write this! If you don't fuel my fire it might be another year before I write again! Ahhhh I know the horror! - 3 Air

"We can't go on like this-or can we?...What do you think?... Some of the time I think its my fault-I've ruined you." - This Side of Paradize, F. Scott Fitzgerald

Dan Humphrey had never let a woman destroy him. He'd never let love tear him down as a man and make him vulnerable and weak. He'd seen it happen too many times by now and he prided himself on having remained above it all. His breakup with Serena had hurt, but he got out first and while he admitted to doing his fare share of pining, he'd kept his composure. He could barely count Olivia and as for Vanessa, he'd come close, but he was determined to remain above it all to the end. Which is exactly what he did. He thought it best to preserve rather than to compromise himself, and though he lost her in the aftermath, he still had an odd reassurance that he was right.

He'd seen Nate Archibald ruined, having not had the virility or the strong will to survive Serena van der Woodsen. Nate had been a shell of a man after Serena had left him, and rumor had it Carter Baizen was falling prey as well just as we speak. And Chuck Bass? Well, for someone to have given every single ounce of himself to another human being, then sure as hell is hot that he'll be a ruined man after he comes out of that relationship. Dan really had no sympathy for any of them, and he secretly held a candle of smugness at the fact that he'd had it all figured out. And that he'd beaten them.

That is, he thought he had.

It was Christmas Eve of 2012 and he'd just heard the notch of the front door to his apartment click shut, and suddenly everything was quiet and still and a little bit sad. She had just left to spend Christmas with someone else who was not him. And once again, as he'd done at least twice before, he'd let her. He'd let her and he'd allowed himself to be the other man. The kept man. They'd fight and they'd break up and she'd be running back into his arms, to Brooklyn of all places and he just let it happen. He felt like a doormat. A fucking doormat and he wasn't in control, he didn't have the upper hand, the moralizing, the self-righteous dialectic. He had nothing to protect him anymore from the bloody, life ruining, heart eating mess that was love.

And when he just so happened to be in love with Blair Waldorf….well, he figured he probably didn't stand a chance from the very beginning.

It all started when he'd inadvertently caught her with her finger down her throat after Dorota's wedding. She blamed it on the alcohol and he agreed, asking if she needed anything to which she politely declined. But for days after he couldn't shake it from his mind that there was more to what he'd witnessed. Her disgusted exterior towards Chuck and their breakup, her snide remarks to him while dancing, her general upbeat demeanor and her smile, of all things, while taking shots with him and her parents. There was absolutely no way that Dan could have really lifted her spirits and distracted her enough, no. And for that, he actually felt a pang of regret.

He never tried to confront her about it. Maybe it was just what rich girls did from time to time. But deep down he knew better, and he felt himself watching her more often, studying her, and becoming more and more engrossed in her life and in her.

They hadn't exactly become friends, but in time Dan had found in Blair someone to read his writing with a critical and intelligent eye. And in Dan Blair had found someone to challenge her. It was a funny sort of companionship, really. They developed a sense of being able to stand each other's company while still never really liking one another.

For Dan, though, he could count the exact instance when she shook him, when she tested him and he figured they were like concussions. They built on one another, so by the lucky number five, he would have considerable brain damage.