[series]: Gossip Girl (TV Show, not book verse)
[character]: Dan Humphrey
[character history / background]:
Wiki makes everything easier. [character abilities]: Being a pretentious douche, posting flyers for his dad's lame band, listening to ~*~sensitive~*~ music, occasional underage drinking, believing everything people tell him provided it is wrong and will mess things up, having a cabbage patch doll, whining about rich kids getting everything, whining about college, whining. Slightly homoerotic subtext with Nate and Chuck. Shockingly good at lying. A much better than average writer, edging on very good. Extensive knowledge of foreign film and classic literature.
...No, really. Dan's kind of useless. Unless you need a lecture on the unfairness inherent in the NYC class system, an intellectual wonk, or a cater waiter. Then he's your guy.
[character personality]: Dan is a Brooklyn boy in a Manhattan world. He attends St. Jude's, a ritzy private school, but looks down on all his classmates as spoiled, useless snobs. The one chink in his anti-Upper East side armor is Serena van der Woodsen; he's had a crush on her since he was fifteen and she paid attention to him at a party. In Serena, Dan sees an idealized version of who she really is; it's more who he wants her to be than anything else. Their relationship is very up and down, with misunderstandings and fights, break ups and make ups. A lot of this centers around Dan's mental image of Serena, and who he feels she should be. Her friendship with Blair, the mistakes she makes, her past... none of these fit into the image he had of his dream girl. Still, Dan loves Serena-- or at least the Serena he wants her to be-- and tries to make it work. Despite everything, the first season starts with the beginning of their relationship, and ends on its close.
The world as seen by Dan Humphrey is a fairly simplistic one; he struggles with the grey areas and uncertainties, which he covers up by being intensely moralistic and judgmental. Occasionally even Holier Than Thou. And being as he sees himself as the perpetual outsider, looking in on the excesses and frailties of New York's social elite but never becoming one of their glittering throng, he's well equipped to cast judgment without ever really looking at his own actions.
He's also an intellectual snob of sorts. He's the guy who can tell you at length exactly why the NY Times Bestseller list is full of crap, and talk for hours over coffee about why the literary industry needs to be revitalized before it lumbers off like some aging dinosaur and dies in a flurry of mass market paperbacks and copies of Twilight. Dan is smart and well-read, and a good writer; knowing he's talented and hardworking but essentially screwed because his family doesn't have the same amount of money or status as, say, Nate-- who, at the beginning of the series, has a guaranteed ride to Dartmouth thanks to his father, a legacy there; Dartmouth being the school Dan would probably shank someone to get into-- just reinforces his bitterness about the situation.
Dan is extremely close to his family, barring perhaps his mother; he and his father are extremely close, and Dan's both insanely protective of and affectionate to his younger sister Jenny. And during season one, as Jenny tries to become everything Dan hates, that helps reinforce his feelings about the GG set; watching someone he cares about try to emulate Blair Waldorf is just beyond the pale. He's even willing to use the system he hates to try and protect Jenny; when he sees her boyfriend kissing another guy and can't get her to listen in person, Dan sends in a tip to Gossip Girl about it. He and Jenny have a long fight about this, where he says that Jenny's letting herself be used; when she shoots back she was using in turn, Dan is shocked into silence, before admitting he sent in the tip himself. Jenny is furious, and points out the elephant in the room: Dan can judge and justify all he wants, but when he starts using GG's tactics to fight his battles, he's in the game just as much as anyone else. The (entirely correct) summation of his actions aren't easy for Dan to swallow, but he quickly lets Jenny back in after her social climb becomes a social swan dive. No matter what he thought of Jenny's actions, she's still his sister, and for Dan that's enough.
Despite his definite bad qualities, Dan isn't a bad guy. He genuinely cares about his family and friends; he's smart, and he can be funny when he's not sticking his foot in his mouth and making the turn from ironic to intensely awkward.
[point in timeline you're picking your character from]: The end of the summer after the season one finale, Much 'I Do' About Nothing, but before S2.