This is my opinion about why Damon should win Elena:
Damon is a much more 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 more behind that mask than we know.
One thing is certain: the main feelings are pain and rejection. While still human, Damon was constantly overshadowed by his little brother, Stefan. He loved his mother very much, yet she had to die in order to bring his little brother to life. As a young adult, their father expresses preference towards Stefan, he constantly has huge arguments with Damon who just stands up to who he is, and if it wasn't for Katherine, he would already have kicked him ouy of the house. But in the end even Katherine admitted she always loved Stefan more.
Damon is a powerful vampire and his Power should have been able to provide him everything, all that he ever wanted, but not everything depends on Power. Love is an emotion that is conquered not handed. And when yo love someone you give...

Name: Damon Salvatore

Nickname: None

Birthday: Some time during the 15th century

Eyes: Black

Hair: Black, straight

Gender: Male

Species: Vampire

Astrological Sign: Unknown

Relationships: Katherine Von Swartzchild and Elena Gilbert though he occasionally shows feelings towards Bonnie McCullough

Parents: Giuseppe, Conte di Salvatore, mother unknown

Siblings: Stefan Salvatore

Powers: Crow form, wolf form, weather manipulation, mind manipulation

Random Facts:

•Damon quotes Edgar Allan Poe's poem, "To Helen," when he attempts to seduce Elena at the dumb supper.
•Damon really likes oranges, as evident in Dark Reunion.

Damon’s appearance:

"He was remarkably good-looking. His face was pale in the artificial twilight, but she could see that his features were cleanly defined and nearly perfect under a shock of dark hair. Those cheekbones were a sculptor's dream."

Caution: may contain spoilers from The Return: Shadow Souls

Also if your a Stefan/Elena shipper.... please dont hate me

Since I began reading the Vampire Diaries series, there hasn't been one moment I haven't thought Elena and Damon belonged together. From the time of their first intense meeting in the gym at her school, I've loved these two together. Not only is Damon hot, wild and dangerous, he is an unapologeticly unique character. While Stefan sits around and whines about the road his life has taken, Damon has accepted his new life and hasn't looked back once. Needless to say, when the Return trilogy came out, I was ecstatic. Three whole books focusing mainly on Damon!! Can I get a hell yeah? In The Return: Nightfall, despite the whole possessed by the evil malach thing, I was so happy a book finally delved deeper into the huge mystery that is Damon Salvatore. Recently The Return: Shadow Souls hit the shelves and, of course, I bought it the same day it came out and finished it the day after. The end was something no one would have guessed. Damon, the Lord of Darkness, the vampire of all vampires, the despiser of humans, became one. Now I...