This is my opinion about why Damon should win Elena:
Damon is a much और complicating character than Stefan. He is strong, intelligent, always wears a mask to hide his true feelings and in the beginning he is being presented to us as the bad guy who is proved not to be so bad after all. In reality, if we look a bit deeper, we will find out that Damon hides much और behind that mask than we know.
One thing is certain: the main feelings are pain and rejection. While still human, Damon was constantly overshadowed द्वारा his little brother, Stefan. He loved his mother very much, yet she had to die...

Right I wrote this in the pick "Who do आप think Damon will be with after the Donnie spoilers?" या something along those lines...and I thought आप should see it.

This is most of the reasons why I am kinda TOO optimistic about Delena being end game in the BOOKS

1) If Stefan and Elena is end game, it is copying Twilight. Yes I know LJ Smith started her series BEFORE Meyer, but she didn't finish it until AFTER Meyer.

2) If they aren't then all their development was for nothing.

3) In Shadow Souls Damon and Bonnie didn't have hardly any scenes together and when they did, nothing was mentioned romanticly...