Dear Elena, yes you heard that correctly. Hell has frozen over. I'm writing it all down. Granted, I'm half a bottle in thanks to my 1950 Chateau Cheval Blanc, a bottle I waited 65 years to open. I used to spend nights sitting in my wine cellar convincing myself I could hear it age, tannins growing, fermenting, but appreciating its beauty didn't make time go by any faster. The bottle just laid there on its shelf, torturing me while I waited for Katherine and time stood still. Eventually I convinced myself that no sip of that wine could ever taste as good as I dreamt it would. And that is the story of why I drink bourbon. I don't know who I am without you, but I know that as long as I'm with you, time will stand still. So who is Damon Salvatore without Elena Gilbert? A selfish friend, a jealous brother, a horrible son? Or maybe with a little luck, I'll do right by you. Because you may be a thousand miles away or a hundred years away, but you're still here with me and my heart is right there in that coffin with you. Until you come back to me.

Damon

It's called dignity. Have some. It's free.

Bonnie [to Enzo]

Alaric: It's been so nice to hear her voice again. Thank you for allowing me to say goodbye.
Jo: Goodbye, Ric.

Damon: Wow. Did I ever mention I like your style?
Stefan: I had a feeling we were going to have to do this the hard way.
Damon: Best...Thanksgiving...ever.

Enzo: Well, if Julian wants it, so do I.
Bonnie: Are we talking about Oscar's car or Lily?

Julian: I assured Lily that there would be no more bloodshed in the house.
Enzo: Did you make any promises about outside?

Matt: Car, I've literally never seen you puke before.
Caroline: That is because I'm polite, not pregnant.

Little tip from a professional. Next time you want to kill a bazillion year old psycho, don't choose a sword from the junior's section.

Damon [to Enzo]

Bonnie: Do you wanna talk about i--
Alaric: Nope.
Bonnie: Okay. Didn't think so.

Bastard links his life to my mom's and then engages in a duel. What is this, Hamlet community theatre?

Damon

When 9 Russians tell you you're drunk, you lie down.

Enzo [to Bonnie]

Valerie: It’s just us. Beau couldn’t bring himself to say goodbye.
Damon: I’m sure he just couldn’t find the right words to say.

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.