HECK YES SHE SHOULD. But not forever. That would leave us with lack of an intriguing plot line. And with lack of plot, a The Vampire Diaries would not be nearly as popular as it is today. And that can't happen, because I love that show. #TeamDamon Seriously though. For a while.
Main characters are better single. There just isn't any way to keep that relationship real when it involves a main character. There is too much going on in their lives to be involved. There would be too much added drama from a relationship between her and Damon. Lastly, things are as they are and shouldn't change. Lastly, she is just too young to have a serious relationship, as are her fans. Elena should not be with Damon.
Elena shouldn't be with Damon because he's selfish with her he'll kill her family just to save her. And ever since she's been with him she's been a different person and her best friend doesn't like it. I remember this one quote that Klaus told Stefan... The only thing stronger than your thirst for blood is your love for this one girl. Also Caroline told her that Stefan was hr epic love.