Content Warning: the following article contains discussions of sexual violence.
There were so many love interests throughout the eight seasons of The Vampire Diaries, that it can be hard to keep track of them all. Some relationships weren't smooth, and viewers couldn't wait for them to end, while others kept viewers invested in the series.
Damon is arguably one of the show's most romantic characters, as when he loves someone he gives them his all. However, if he's not feeling it, Damon will quite literally throw them aside like they mean nothing. Some relationships that involved Damon were really great, while others were incredibly stormy.
8 Damon And Sybil
Sybil contorted Damon's memories of Elena and made him think that she was the girl he was in love with. Season 8 of The Vampire Diaries was rough for Delena fans, but it also proved just how powerful the love between them was.
Sybil's plan failed after Damon's memories started making their way through the fog and he realized that Sybil had been manipulating him and that their relationship was not something he was consenting to at all. Sybil is his worst love interest by a landslide and what she did was truly horrible.
7 Damon And Caroline
Damon's treatment of Caroline was one of the many things that made viewers hate Damon from the start. While he and Caroline were sleeping together, he began to feed on her against her will. Caroline tried to escape from Damon, but he compelled her to be okay with everything he was doing to her, a non-consensual violation of her will.
Damon crossed many lines in this relationship and never should have gone anywhere near her.
6 Damon And Andie
When Damon and Andie first started dating, he did the exact same thing to her that he did to Caroline. He slept with Andie, fed off of her, and compelled her fear away. However, Damon started to show some real development and it was clear that he had grown to care for her.
He stopped compelling her and they formed a truer relationship, but it doesn't excuse Damon's past behavior and assault of Andie. When Stefan killed her to save his brother from Klaus, Damon was heartbroken over her death. Still, as far as relationships go, this one is not one to be lauded.
5 Damon And Katherine
Katherine was Damon's first love and he devoted over 150 years to her. When he believed she was trapped in a tomb under Fell's Church, he spent most of his existence trying to find a way to free her.
But Katherine was never in the tomb, and she hadn't cared about Damon as much as he did for her. There were times when Katherine admitted to loving Damon, but it was nothing compared to how she felt about Stefan. The relationship was one-sided and almost impossible to root for.
4 Damon And Rebekah
Damon and Rebekah were more sexually involved than romantically involved. Damon flirted with her to gain her trust on more than one occasion, and he and Rebekah ended up sleeping together as a way to lash out at the people they cared about.
Out of the Salvatore brothers, Rebekah cared more for Stefan, and it didn't bother Damon in the slightest. There weren't any sparks flying between them, but Damon had more potential with Rebekah than several of his other love interests.
3 Damon And Rose
If Damon hadn't been all about Elena, he and Rose would have stood a real chance. Rose was always on Damon's side and became someone that he could confide in. She understood Damon like no one else did and they had good romantic chemistry.
Rose was well aware of Damon's feelings for Elena, and she made it clear that she couldn't fully be with someone who was in love with another woman. After Rose is bitten by a werewolf, Damon takes care of her and makes sure she spends her last day in paradise.
2 Damon And Bonnie
Bonnie and Damon were never in a romantic relationship in the show, but there were plenty of fans who wanted them to be together. The two had a romance in the books and both versions of Bamon had chemistry.
Damon and Bonnie started off as enemies, and it took six seasons for them to become anything more than begrudging allies. But after being trapped in a prison world together, they became best friends who cared about each other deeply. Bonnie was the only person Damon had ever put over Elena, and their friendship would have been a great foundation for more.
1 Damon And Elena
No matter how viewers felt about Damon and Elena's relationship, Elena is Damon's only real love interest for the majority of the series. After he moves on from Katherine in Season 1, he falls so helplessly in love with Elena that anyone else he was with was only there to pass the time.
Damon becomes a better man for Elena, and the transformation he undergoes to be with her is impressive. Damon and Elena's love story is at the front and center of The Vampire Diaries, and credit needs to be given where it's due.
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