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I'm gonna be completely superficial for a minute here and say that the two of them look ridiculously GORDEOUS together <3
I don't want any of them to die, I'm attatched to every single one *sobs*
But, if I really had to choose, I'd say either Matt or Jenna (because, as everyone else mentioned, Alaric's in the pictures). I have an inkling it might be Matt though because unless "the powers that be" can get David Anders (actor who plays John Gilbert) to stay permanently, Elena and Jeremy would have no legal gaurdian =S I'd hate for it to be Matt though because I'm pretty fond of him, but he's the only one who wouldn't really hurt the story at this point =(
I do think that a potential Damon-death would make for some awesome angst though (because we all know that there's no chance in hell Damon, Elena or Stefan will ever die, that's be the end of the show lol) *-)
I agree with most of whay you're saying, particularly that Bonnie would have a problem with Damon as he is right now and that's why I honestly can't understand how people can hate on Damon trying to become better and yet want him with Bonnie when there is no chance in HELL that Bonnie would accept him unless he got his act together. In fact, I can say with confidence that Bonnie would want him to make the exact same changes Elena wants.
I'm honestly getting the impression that too many people are looking at this with their "shippy blinders" and hating on the fact that Damon is changing because of Elena more so than the fact that he's changing. Again, obviously not everyone, but I did get that impression from quite a few people.
Personally, I like complex characters that struggle and that bring the good and the bad to the table, which I feel Damon is doing at this point. The essence is still there, he's still humorous, engaging, and morally grey (and I'm sure he'll always be), but there's more to him now and I like it. There are more than enough one-note villians IMO for him to be another.