Lily: I took your advice and I've been dabbling on Stefan's computer. What a wondrous invention -- all that knowledge.
Damon: And videos of cats riding robot vacuum cleaners.

[to Elena] You're lucky you're adorable because your eternal optimism is super annoying.

Elena: [to Lily] You've been in here for over a century.
Damon: Yeah, I would've come by sooner but I thought you were safe and sound in the family crypt. My bad.

Lily: Damon?
Damon: Hello, mother.

Elena: Is this presentable attire by 1903 standards?
Damon: Whoa, who said you were coming?
Elena: To meet the woman who gave birth to the two epic loves of my life? Me.

Listen, we go in, we grab my mom, she flips Stefan's switch, he triggers Caroline, emotional dominoes, heyyyyyyy! Everybody wins.

Damon: You don't have to pretend, Bon. I'm like a fever you can't shake.
Bonnie: Yeah, yeah, like a disease.

Damon: So Saint Caroline keeps her halo even with no humanity.
Stefan: Yeah, until she snaps and strangles somebody with it.

Stefan: I think you were wrong about Caroline. I realize that I may not be able to explain what I feel for her, but it is something, and yeah, maybe all love isn't true love in the messed up way that you and I have experienced it, but I think this could turn into something even better.
Damon: Well then, brother, stop wasting your time sitting here with me.

Liz Forbes was my friend. In her last moments she asked me to pass along a message to her daughter, but I cut her off before she could say too much, told her she could tell Caroline herself. She didn't get that chance. Your mom wanted you to know how proud of you she was, and she should be. You're a beautiful, strong woman, a generous friend, and a bright light in a sea of dark. She said you were extraordinary, and you are, and so was she. Liz was a hero to this town, she was a hero to all of you, and she was a hero to me. Goodbye, Sheriff. You will be missed.

Damon: No, I'm not done. And I will never be done. I am not a nice person. I should not have to stand in front of the entire town and pretend to be a nice person. This is Liz having a last laugh from the great beyond.
Elena: Hey, you are nice...

Stefan: Look, something happened between Caroline and me.
Damon: Oooh, finally.

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.


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.