Bonnie McCullough ( The Vampire Diaries (books) )
blytheandbonnie ♦ ★★★★★★★★★★
Bonnie has bee Damon's constant companion. They've traveled through three worlds together. Oddly enough, when they first met in a world called Rowan, Damon didn't even remember meeting Bonnie. She came from a future in which the two of them were lovers and in which he turned her into a vampire however. As such, he began to take responsibility for her, at first, as a parent or sire, but eventually as someone who loved her very much. Despite their ups and downs and Damon's insistence that nothing lasts forever where vampires are concerned, when Bonnie asked him to marry her, Damon said yes.
Buffy Summers ( Buffy the Vampire Slayer )
kiss_evilgoodbye ♦ ★★★★★★★☆☆☆
Despite the fact that they're technically supposed to be enemies, Damon and Buffy get along surprisingly well. They met on Damon's arrival, when he joined the Bete Noire police force in order to keep his ear to the ground about vampire shenanigans. Despite his intentions, it turned out, Damon was actually pretty good at being heroic. Even if he didn't want to admit it. He and Buffy teamed up several times, particularly during Angelus' reign of terror. Though they've had some differences (Buffy once, justifiably, hit him over the head with a shovel), Damon considers Buffy to be one of his best friends in the city.
Jack Harkness ( Torchwood )
capj_harkness ♦ ★★★★★★★★☆☆
Damon first met Jack Harkness in a world called Rowan. He then met him in a world called Willaknapp. Yet again, he met him Bete Noire. Needless to say, Jack didn't remember any of it. But Damon didn't mind. In Bete Noire, he and Bonnie quickly befriended Jack, or as Damon took to calling him, "honeyboy." When lists of inhuman creatures were released and Jack's name was on one, Damon offered him shelter in the villa. They've been good friends ever since and Jack was one of the first people to keep Damon's secret about being a vampire.
Raylan Givens ( Justified )
iwasjustified ♦ ★★★★★☆☆☆☆☆
Raylan Givens is Damon's boss at the police department. As such, they are natural enemies. Yet they get along well. Since Damon is efficient at his job and hasn't stepped out of line, Raylan has no idea of Damon's true motives for being on the force. Damon, however, has weedled some massive secrets out of Raylan. Namely, that he is a werewolf. Now, Damon hopes to use that secret as leverage. He hasn't really had the need to do so yet, but he's always on the lookout. As a person, he actually doesn't mind Raylan that much.
Elena Gilbert ( The Vampire Diaries (TV) )
braveandstupid ♦ ★★★★★☆☆☆☆☆
Awkward does not begin to describe this relationship. Elena Gilbert has the same name as the woman Damon last loved. Who, sadly, died tragically in front of him. But Elena has a different face and a different history. She knows very little about Damon, not even that he's a vampire. Yet. Hilarity will doubtlessly ensue. In the meanwhile, Damon is keeping her at arm's length. Watching out for her, but always from a bit of a distance.
HMTL by Creatively @ DW