Vampire Diaries: Every Damon Relationship Ranked From ‘Catastrophe’ To ‘Meant To Be’

The Vampire Diaries was no stranger to throwing romance at fans, even when nobody asked for it. Well, that's the price you pay for having two hot guys as the main characters.

It's true that the Salvatore brothers were heartbreakingly good-looking, but one of them was actually a little more successful at making girls fall for him. And yes, it's Damon.

So let's take a look at all of his romances and try to understand which ones were better off axed, and which ones were a blessing for him and for us.

8. Sybil

This pairing happened during the most horrible season of the show for Delena fans, season 8, when Damon was suffering from the memory loss spell that Sybil put on him to make him think that she was the woman he loved. She was successful for a while, but then Damon's memories started to come back and he realized that Sybil had manipulated him.

7. Caroline

Damon and Caroline being together was probably the worst thing that ever happened to the poor girl. Damon was truly hated by the fandom for everything he had done to her.

When he was with Caroline and she was still a human, he started using her as a blood source... Of course, against her will. And when she tried to run away from him, he forced her to agree to everything he was doing to her. This "relationship" was the most disturbing and should never have existed.

6. Andie

Their relationship with Andie started out the same way as with Caroline, but somehow Damon really started to develop genuine feelings towards her. Of course, after that he stopped compelling her.

When Stefan was forced to kill the woman to save his brother from Klaus, Damon was devastated. But still, even that doesn’t excuse him from his past behavior towards Andie.

5. Katherine

First love is claimed to be the strongest. Well, for 150 years this statement was true for Damon. He thought that Katherine was trapped in a tomb beneath Fell's Church, so he spent many years trying to find a way to free her and be with her.

But in reality, Katherine was not worth it. For starters, she wasn’t in the tomb, and what’s more, she never cared about Damon. This relationship was absolutely one-sided.

4. Rebekah

Although their relationship was mainly sexual and there was almost no romance, many fans believe that it could have been something more. Well, compared to many of Damon's other love interests that made much less sense. If given a real chance, they could have made their couple really entertaining.

3. Rose

Another couple that really stood a chance, if Damon wasn’t so hung up on Elena. Rose was really close to him and understood him like no one else. They really had this spark between them, but even that was not enough to make him love her the same way he loved Elena.

2. Bonnie

This is probably the most exciting pairing in the whole show. To start with, Damon and Bonnie were never involved romantically in the series (although they were in the books), but fans kept shipping them all the way till the end of the show.

They started out as enemies, but in the long run they became the best friends with the strongest chemistry. Bonnie was the only person Damon had ever put over Elena, and their friendship would have been a great foundation for something more.

1. Elena

Not very surprising, right? Of course, Elena should be number one on this list, because let's face it, these two are made for each other, and that's not just a nice thing to say when describing a great couple.

Damon literally became the best version of himself to be worthy of Elena. And that's something that only a person with strong and deep feelings can do. Damon and Elena's love story is the heart of The Vampire Diaries, and you have to give credit where it's due.