The Vampire Diaries Romances: RANKED!

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10. Jo and Alaric

Jo and Alaric
Alaric's good looks helped him wind up in several relationships throughout the show's run. Unfortunately, Kai brought this one to a grinding halt.

9. Jenna and Alaric

Jenna and Alaric
Aunt Jenna was dating Alaric early in the show's run and they were great together. If there was no supernatural forces in Mystic Falls, they would probably still be a thing.

8. Stefan and Valerie

Stefan and Valerie
Stefan has a knack for hiding past relationships from his lovers. His short-lived relationship with Valerie was full of tragedy, but you could tell there was something between them. That's probably why they made a go of things again all those years later.

7. Stefan and Rebekah

Stefan and Rebekah
Part of the reason Rebekah became such an intriguing character was that she shared a lot of history with Stefan, who was still pining after Elena. Watching the layers of their relationship unfold in flashbacks was great and the whole pairing pissed Elena off, so there's that.

6. Stefan and Katherine

Stefan and Katherine
Stefan was really starting to feel something for Katherine back in Season 5. Heck, he even managed to stop her from throwing herself off the bell tower when she was human. They have a lot of history and a whole lot of chemistry.

5. Bonnie and Enzo

Bonnie and Enzo
Bonnie and Enzo were such a random pairing on The Vampire Diaries Season 7. It was clear they really loved each other, but it's just a shame Arkadius was around and Stefan opted to make Enzo part with his heart. Will they get a happy ending in the afterlife? Probably.

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Vampire Diaries Quotes

Dear Diary, a chipmunk asked me my name today. I told him it was Joe. That lie, will haunt me, forever.

Damon

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