{ updated 01/29/2011
katherine pierce
There's not a lot to be said about Katherine except that she's the love of Damon's life, and he's spent the past 145 years trying to rescue her-only to discover that she's never needed rescuing, that she doesn't really even give a damn about him. So now he's looking for anything he can find that might suggest that he wasn't kicked to the curb; he's invested too much in her to accept so easily that she played him for a fool. But there's a definite sense of bitterness and betrayal, as well: no matter how desperately he's clinging to the hope that there's an explanation for why she abandoned him-that she does love him back, that his whole life hasn't been a lie-a part of him knows better. And Damon does not take heartbreak lightly. His love for Katherine is not born out of anything healthy, but it's very real.
stefan salvatore
"For better or worse, he believed in his brother's unerring tendency to turn up like a bad penny."
HIS BEST BRO. Once upon a time. Now Damon kind of hates Stefan a lot and resents him even more for...well, everything. For what happened to Katherine, for what happened to him, for that small and admittedly pathetic part of him that believes Katherine may have been Stefan's more than she was ever Damon's. Still, Damon cares more for Stefan than he's willing to admit. When it comes down to it, Stefan is still his little brother, the kid he taught to play football way back in the day, the one person who's known him all of his very long life. Deep down, he misses what they used to have, although he will never acknowledge it. What this heartwarming fact means is that Damon will not bat an eyelash if Stefan ends up getting stabbed in the face-so long as he's the one doing the stabbing. Anyone else who tries to take a turn should run very fast.
elena gilbert
"At least if they were screwed, they would be screwed together now."
His original attraction was based on a) that she looked like Katherine and b) Stefan was dating her. But he's grown a bit fond of her-she's fun company and for some inexplicable reason, she seems to think Damon is worth something. There's no question that he'll drop everything to help Elena out if she were ever in trouble. Given that this is Damon we're talking about, this is a pretty special position that Elena holds. It's not an exaggeration to say that she's his first and only friend. He loves her, which makes things complicated considering she's dating his brother. He's never voiced this out loud, of course, but there's something to be said in the fact that he's never denied it, either. The truth is, she makes him want to be a better person. It might not be for the most altruistic reasons because a lot of it has to do with her approval, but it's a step forward at least.
alaric saltzman
"Alaric knew their relationship was awkward at best (yeah, he hadn't forgotten that... late night encounter)."
Damon slept with Alaric's wife, turned her (she asked him to, okay), and then killed Alaric when he came to confront him about this. Then he revived, a few things happened, and now they're sorta-allies, sorta-kinda-semi-friends. Inasmuch as Damon has friends. He doesn't mind Alaric's company, though, and there's something about Alaric that Damon likes. He also helped Damon rescue Stefan which yes, fine, Damon appreciates that. Let's just say that on a good day Damon would hesitate to kill him and Alaric is someone he would actually go out of his way to help. Plus, they've both been fucked over by the women they love so Damon can sympathize a little on that level.
IN SUMMATION:
bella swan
Damon was unaware that Bella was the Bella Swan when he first met her, but after having met Edward Cullen, he's definitely made the connection. There can't be that many Bella's around who smell attractive and have a giant engagement ring on their finger. They've met once since then and talked a little. Damon likes her well enough, but the fictional thing is...pretty weird. He can't help but associate her with Elena in some ways.
edward cullen
"I never really understood the whole fanatic craze related to vampires."
Edward came up to Damon to ask him about Twilight of all things, and then said his name was Edward Cullen. (DOT DOT FUCKING DOT). Anyway, he thinks the whole thing is surreal as fuck, but he's rolling with it because what else can he do. The guy sparkles, man. He finds it no coincidence that Stefan has become friends with Edward. That Edward is from Twilight has, in some weird way, made Damon accept Edward with less hostility if not necessarily less suspicion since it's just...hard to see him as a threat when Damon knows him from the pages of a badly written teen romance. And he did stick around to help Stefan when Stefan decided to be an idiot and sedate himself. Damon will never acknowledge that this as a reason for why he's okay with Edward, but it is part of it.
claire littleton
"Even the pitch of his voice was the same, and the incredulous raise of his brows. Boone used that exact look."
Claire came up to Damon freaking out about him being dead (true) and a plane crash (...less true). Apparently, he looks a lot like her dead friend Boone. Damon has no idea what the hell this is all about, but he's definitely more than interested. He was ready to exploit this at first, but then she came to his rescue one night. To express his thanks, he decided to eat her. He was hungry, okay? Claire wants him dead because he's a dick, and Damon wants her dead because she knows what he is. At this point, it's a case of who gets there first. To be fair, he doesn't dislike her as a person. She's just gotten in the way.
claire bennet
"He just seemed like what she'd probably call one of the friendlier patients in the institute, to be entirely honest."
Damon actually genuinely likes Claire Bennet. She's cute and makes pretty decent company, and she didn't annoy him which is more than he can say for most humans. Especially teenagers. She reminds him a bit of Elena, in some ways. He knows she's met Elena and Stefan both, which is largely what still keeps his interest. Plus, she clearly likes him, too, and people who like him are useful. He's not planning to eat her. Not yet, anyway.
klavier gavin
"Thankfully, this one -- Salvatore, was it? -- didn't seem like a raving lunatic."
Damon's new roommate. They've only talked a bit so Damon doesn't know what to make of him yet, although the guy was helpful with new information. Klavier also had the misfortune of catching Damon in a bad mood one evening even if that didn't go nearly as bad as it could've (a.k.a. no one died). So far, they're on neutral ground which is about as much as you can ask for with Damon. He doesn't dislike Klavier, but he wouldn't bat an eye if the guy dropped dead out of nowhere.
wally west / the flash
"It wasn't like helping someone gave you automatic rights to bugging them, after all."
They met when Wally helped keep Damon from falling on his face. Wally also managed to keep Damon from tearing someone's head off, which is actually pretty impressive. Damon's not quite certain what to make of Wally as of yet. He's definitely not a threat, though, and he seems to know something...interesting. Coupled with how goddamn nice he is, he's worth keeping around. Damon knows the benefits of having people on his side, after all, and he prefers to do that with someone who's naturally trusting. Makes the job easier.
fujiwara yoshiko
" Self-confidence. It had certain layers of amusement to it."
First person he met in the morning. They never quite introduced themselves so he doesn't know her name. He does know that she isn't human, though, or at least self-identifies as such, and he knows that she somehow sensed what he was. He's...curious, but she's not someone he'll involve himself with too deeply. While he does enjoy her somewhat-she's different from the usual; a nice change of pace-she's obviously not the type he can easily use and discard and he doesn't like that she pegged him as a supernatural creature. At the moment, she's useless to him at best, and a liability at worst. Still, he'll keep her in mind if anything comes up.