Katherine: So, here we are: the brother who loved me too much and the only who didn't love me enough.
Damon: And the evil slut vampire who only loved herself.

Katherine will only rip your heart out. Let me do it for her.

I look at you and I see myself. A less dashing, less intelligent version.

Mason Lockwood? Werewolf thing aside, the guy's a surfer.

I was afraid you were gonna be some beast master with no affinity for pain.

Your search for life's purpose is as obvious as it is tragic.

Liz: My daughter is gone.
Damon: You have no idea how wrong you are about that.

You're my friend.

Damon: I don't peace.
Stefan: Oh. Consider it opposite day.

I tried to kill a werewolf, I failed. Now I feel like I'm not living up to the version of my best self.

Katherine: Bad day.
Damon: Bad century.

Damon: I always pegged you for a lone wolf.
Mason: I'm sure I wasn't half the lady killer you were.

Vampire Diaries Quotes

You want a love that consumes you. You want passion and adventure, and even a little danger... I want you to get everything you're looking for. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena.

Damon

He's your first love. I intend to be your last. However long it takes.

Klaus [to Caroline]