It just occurred to me that the only way for Delena to have a shot was for Elena to die, not because Damon is right for "Elena the vampire" and Stefan is right for "Elena the human" but if memory serves, Damon was about to be killed by possessed!Alaric and the only thing that saved him was Elena drowning, thus severing the magic bond that the witches had on Alaric. So, in a weird way, fate made this possible, because if Elena had lived, Damon would have most likely died that night, and she would have never have had the opportunity to reassess her choice.
That night, I think Elena was deeply torn. In my opinion, she chose Stefan partly out of loyalty, but also out of fear about whether she and Damon would really "work" as a couple or would he disappoint her.
In the past few episodes, Stefan has lied to her, basically made her feel "defective"/needing to be "fixed", risked her brother's life on multiple occasions (supposedly to "cure" her). Damon, while angry that she "died" accepted the reality of her new existence. He knows that baby vamps are moody and mess up, so he's shown her an amazing amount of patience, even when she was freaking out after the frat party and essentially insulting him. He tells her what Stefan's up to. She can be honest with him, and he'll be practical about finding a way forward for her. I think what doomed Stefan and Elena at present was that the trust was gone - Elena still cares for Stefan but you can't have intimacy without trust. Damon has come a long way from the loose canon that snapped Jeremy's neck in a hurt rage in Season 2, and Elena knows it. His acceptance and unwavering affection were exactly what she needed when she was feeling very depressed about being such a failure as a newbie vamp. I think Damon, and the feelings they share, gave her hope that things will be ok/get better in a way that Stefan really hasn't.
And let's be real, she's had a bit of a crush on him since Season 1 - look at how she recalls the Miss Mystic Falls dance? It clearly wasn't 100% platonic, although she was still was committed to Stefan at the time. She felt enough for Damon in Season 2 to kiss him on his "death bed", and admit she likes the "morally ambiguous" Damon just as he is. And, if Jeremy had not been there the night of the motel kiss, I'm sure Delena would have "happened" right then and there.
I kind of love that Elena just "went" for it with Damon...she's died (multiple times already); she's not with Stefan; what more is there to fear about giving into her feelings?
I sincerely hope they don't go the "sired" route with these two - but I don't think it really matters one way or the other. She initiated things going to the next level. These feelings were there when she was human. I just hope that these two get another "moment" where there's no speculation about either of their motivations.
Edited by Sedruol, Nov 30, 2012 @ 8:54 PM.