The TV show The Vampire Diaries had it all. From fights and mysteries to epic romances and even some romantic failures. As it ran for eight seasons, the creators of the series had plenty of time to build the relationship between different heroes and villains. Sometimes they ended well, but most often romances continued The Vampire Diaries led to tragic endings.
While the show primarily focused on Elena Gilbert and the Salvatore brothers, Stefan and Damon, it also made the time necessary to create more other relationships. And while it’s hard to pick the best and the worst, some conditions worked really well, while others fell flat.
Updated January 6, 2022 by Hilary Elizabeth: Romance is obviously the heart of The Vampire Diaries as a series. Given that there have been so many conditions during the show, it’s important to recognize all the ships that fans will never forget (as well as the ones they wish they could forget).
The best Vampire Diaries couple
Nora and Mary Louise
When a couple stays together for more than a century, it is safe to assume that it is true love. This was also the case for the vampires Nora and Mary Louise, who began dating in the 1880s – in times when a romantic relationship between two women was a big taboo.
They had their arguments, but worried about each other. The relationship continued until they sacrificed their lives to destroy Rayna Cruz’s weapons.
Stefan and Katherine
At the beginning of their dynamic, it looked like Stefan hated Katherine and would have very little to do with her. He even convinced himself that he was never in love with her in the first place, that it was all a lie caused by Katherine’s coercion.
But the two still managed to find their way back to each other, and it seemed that they could actually revive some kind of relationship, especially when Katherine became human. Unfortunately for them, none of them survived in the end. And while their relationship was clearly not healthy, it was at least compelling to watch.
Jeremy and Anna
Unlike Bonnie and Jeremy, these two had real chemistry between them. Anna may have lied about being a vampire, but Jeremy quickly forgave her and they continued their relationship.
At first, Jeremy used Anna to learn more about vampirism, but eventually he fell for her just as hard as she fell for him. And when Anna died and later returned temporarily as a ghost that Jeremy was able to see, he admitted that he was still in love with her.
Tyler and Caroline
Eventually, Caroline and Tyler’s relationship went out because each character became more engrossed in other things, and they just kind of grew apart. However, they were one of the most important conditions in The Vampire Diaries, and Tyler and Caroline both made each other better people.
The star-crossed loving aspect of a werewolf and vampire falling in love certainly made their romance interesting, but Caroline’s journey that helped Tyler with his transition was a truly fascinating plotline in itself.
Bonnie and Enzo
Both Bonnie and Enzo knew of a lot of tragedies and faced some serious problems in life. It was one of those things that brought them together.
Bonnie was not very fond of Enzo at first, but he won her over in the end. Their relationship, unlike others in the show, was not so full of drama and danger. But even though it did not have a happy ending, Bonnie and Enzo were happy while it lasted and they seemed to be each other’s true epic loves.
Klaus and Caroline
Unlike many of the other conditions in The Vampire Diaries, the will-they-do-not-want-the-dynamic between Klaus and Caroline never really went far beyond that. However, that did not stop this potential pairing from becoming one of the most popular ships in the series’ history.
The chemistry between them was out of the charts, and even though they never made things official, Klaroline had so many amazing scenes that they are undeniably one of the best romances in the series.
Stefan and Elena
Although Stefan and Elena did not end up together, and their initial attraction could potentially be explained by their dual double status, they were the relationship that really started The Vampire Diaries.
The love they shared with each other was heartfelt, simple and pure, and it made them appeal to audiences all over the world. Elena may have ended up with Damon, but many fans were still excited that Stefan and Elena would be reunited until the very end.
Damon and Elena
This was a sore spot for many fans of the show, but despite the way Damon had treated Elena in the beginning, they still ended up together. He had many negative traits and some fans even thought Damon was insoluble, but he tried to be a better man for Elena.
They parted ways during the show, but reunited after everything was said and done. They started a family together when Damon became a human and lived happily ever after, according to the last episode of The Vampire Diaries. And despite any controversy, the Delena was undeniably the most popular ship in the series.
The Worst Vampire Diaries-par
Jeremy and Vicki
Jeremy really liked Vicki, and even though she seemed to have returned his feelings at some point, the relationship between them never worked. That was at least in part because Vicki secretly joined Jeremy and did not want anyone to know about it, least of all Tyler, the guy she actually seemed to have an interest in.
Vicki also tried to persuade Jeremy to take drugs with him and had a bad influence on the younger guy. Eventually, she also tried to kill both Jeremy and his sister Elena when she became a vampire.
Damon and Andie
Damon’s brief connection to Andie Star was essentially just a renewed version of his so-called “relationship” with Caroline. Of course, Andie said she would have been with Damon even if he did not force her, but he did not stop manipulating and controlling her anyway.
It seemed that Damon pretty much saw Andie as a useful tool and a way to kill time, and although Andie’s untimely death suggested that his feelings might be a little deeper, their relationship was brutal.
Bonnie and Jeremy
Bonnie may have found her perfect partner in Enzo, but he was not her first boyfriend, not by a long shot. For a while, she and Jeremy dated. But their relationship had several problems, beginning with the lack of chemistry and ending with the fact that Jeremy was still in love with Anna for a significant amount of time when they were together.
They came together to break up later (usually because one of them died temporarily) and did this cycle several times before interrupting things forever. Their relationship had a lot of drama, but it was never particularly interesting.
Tyler and Vicki
Apparently The Vampire Diaries wanted to establish that Tyler was the absolute worst right out of the gate as he was essentially on the verge of sexually assaulting Vicki before Jeremy intervened. And even though Tyler was a little nicer against Vicki in the following episodes, that does not say much.
He still treated her like nothing more than a hookup and was ashamed to be with her, and their whole connection seemed designed as an obstacle that Jeremy and Vicki had to overcome in order to start their own relationship anyway.
Damon and Caroline
Relatively early in the first season, Damon and Caroline had a very unhealthy relationship. Caroline was attracted to Damon, but he used her only as a walking blood bank, errand girl, and as a way to get closer to Elena.
He drank Caroline’s blood against her will, insulted her and terrorized her. And when he finally got bored of her, he tried to kill her – a plan that Stefan luckily stopped. Although it seemed that they later developed a strange frenemy-style relationship, they were undeniably one of the worst couples on the show.
Katherine and Damon
Katherine seemed to have genuine feelings for both Stefan and Damon, and Damon obviously loved Katherine for years, but their relationship was pretty toxic. Katherine had very little affection for Damon and she preferred Stefan. Still, she led Damon on, making him believe she had been trapped for over a century, and she did not even want to get in touch with him, even though she was free all the time.
Despite all this, Damon was still ready to forgive her when she returned, but Katherine crushed him by saying she had never loved him in the first place.
Caroline and Alaric
Given that Caroline was much younger than Alaric and he used to be her high school teacher, this relationship felt like a bad idea from the start.
It was borne of fact Caroline had given birth amazingly to Jo and Alaric’s children thanks to a magical baby swap. But even though they were engaged at one point, their relationship never felt like a real romance, and it was far more eerie than compelling.
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