Damon: Now I know why Stefan digs you. You're a take charge kind of girl.
Valerie: And you're a self-serving narcissist.

Hashtag, you're welcome. Are hashtags still a thing? It's been three years.

Stefan: If there is even a fraction of you that cares about me, do not walk out that door.
Damon: Save a bottle of that good bourbon for me, brother. We’re gonna need to sort all this out in about sixty years.

I’m not a good brother when I’m not with Elena and when I’m not a good brother people get hurt.

Damon: Look, I’m selfish, narcissistic, prone to unnecessary bouts of violence...
Rayna: Tell me again why I shouldn’t be killing you.

Rayna: You want me to go against my very nature because he’s your family?
Damon: Pretty much.

Rayna: What’s next? It puts the lotion in the basket?
Damon: It wouldn’t have to if it just stayed dead.

Once whatever crap Enzo gave you is out of your system and magic works on you again I’m going to give you my blood and heal you. Okay? But in the meantime, there’s something Iw ant you to know. You are a terrible friend, you know that? Do you have any idea what I’d have to go through if you’d died today? Years of guilt. Crippling, self-loathing guilt. Not to mention the resentment I’d feel if I was forced to break in a new drinking buddy. You’re not supposed to die for me, Bon. Neither is my brother. But no matter what I say or how hard I drill it into your skulls, you’re not gonna stop trying, which is why I have to take myself out of the equation. It all ends tomorrow. You’ll never have to worry about me again.

Doubtful. We only go to New Orleans for crappy booze and Klaus blood.

Damon: Go ahead. Let it all out, Bonnie. I’m a vile cheater. I couldn’t even wait a year.
Bonnie: Are you kidding me? The last thing anyone wants to deal with for the next six decades is a cranky, bitter, sexless Damon Salvatore, okay?

You wanna send me back to Hell? Well let me tell you something, lady. I’m already there.

Enzo? Remember Thanksgiving in 1953? We were locked up and I told you I was thankful for you through that little hole in the wall. I take that back.

Vampire Diaries Quotes

Oooh, you know I don't know. Every time we try and go on a date you get kidnapped, I get sent to a prison world, or your feelings get compelled away...

Damon

Damon: My new girlfriend. Andie Starr. Action News.
Alaric: It's not called Action News.
Damon: I know. I like just saying it.