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...

Mystic Falls is a picturesque town located in the southern area of Virginia. Aside from the towns foundation in 1859 (in the series timeline) by the Founding Families, the town also has a long history of vampires, witches and werewolves. As the Founder's Council, they secretly guard the town mainly from vampires, and they are seemingly unaware of other supernatural beings, such as werewolves and witches.

The Founder's council:

The Founders Council is an association of the Founding Families, townspeople descended from the original settlers of Mystic Falls, as well as various municipal officials....

Chapter 1:
December 1
Dear Diary,
I had a feeling that something terrible was going to happen today.
I don’t know why I wrote that. It’s outrageous. I have no reason to be upset, but every reason to be happy, but here I am at 8:30 in the evening, scared. But that doesn’t explain why I feel so lost.
The day before I left Virginia Beach, while I was gather a bag full of clothes. I came across five old journals, leather covers with old coffee stained pages. They were my great Uncle Jonathans’ journals; he was one of the first founder families in Mystic Falls and believed that there were vampires...

HEARTLESS

KANYE WEST BEAT
VAMPIRE DIARIES THEME

Hope you enjoy it!

in the night i hear 'em talk
the coldest story every told
somewhere far along this road
he lost his soul to a woman so
HEARTLESS

ohhh how could she be so heartless
how could she be so heartless how
could she be so cold

her name was Katherine
and she was cold
she was a vampire
mean and old

took the love of both Damon and Stefan Salvatore

how could she be so heartless
how could she be so cold

15th century love all gone
but she got a hold on Damon's heart
he wont let go
Stefan could tell true love's kiss so he knew what he felt for Katherine could...