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This is my opinion about why Damon should win Elena:
Damon is a much thêm 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 thêm behind that mask than we know.
One thing is certain: the main feelings are pain and rejection. While still human, Damon was constantly overshadowed bởi 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) bởi 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 ma sói 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 ngày 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...