The TV show The Vampire Diaries had it all. From fights and mysteries to epic romances and even some romantic letdowns. Since it ran for eight seasons, the show's creators had plenty of time to build the relationships between various heroes and villains alike. Sometimes they ended well, but more often than not, romances on 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 that necessary to create multiple other relationships. And while it's hard to choose the best and worst, some relationships worked really well while others fell flat.
Updated on January 6th, 2022 by Hilary Elizabeth: Romance is obviously the heart of The Vampire Diaries as a series. Considering that there have been so many relationships throughout the course of the show, it's important to recognize all of the ships that fans will never forget (as well as those that they wish they could forget).
The Best Vampire Diaries Couples
Nora & Mary Louise
When a couple stays together for well over a century, it's safe to presume it's real love. That was also the case for the vampires Nora and Mary Louise who started dating in the 1880s - in times when a romantic relationship between two women was a big taboo.
They had their arguments but cared about one another. The relationship continued until they sacrificed their lives to destroy Rayna Cruz's weapon.
Stefan & Katherine
At the start of their dynamic, it looked like Stefan hated Katherine and wanted to have very little to do with her. He even persuaded himself that he was never in love with her in the first place, that it was all a lie caused by Katherine's compulsion.
But the two still managed to find their way back to one another and it looked like they might actually be rekindling some kind of relationship, especially once Katherine became human. Unfortunately for them, neither survived in the end. And while their relationship clearly wasn't healthy, it was at the very least compelling to watch.
Jeremy & Anna
Unlike Bonnie and Jeremy, these two had genuine chemistry between them. Anna may have lied about being a vampire, but Jeremy quickly forgave her and they continued with their relationship.
At first, Jeremy was using Anna to learn more about vampirism, but in the end, he fell for her just as hard as she fell for him. And when Anna died and later came back temporarily as a ghost who Jeremy was able to see, he confessed he was still in love with her.
Tyler & Caroline
Ultimately, Caroline and Tyler's relationship fizzled out because each character became more consumed with other things and they sort of just grew apart. However, they were one of the most important relationships in The Vampire Diaries, and Tyler and Caroline both made each other better people.
The star-crossed lovers aspect of a werewolf and vampire falling in love definitely made their romance interesting, but Caroline's journey helping Tyler with his transition was a really fascinating plotline in its own right.
Bonnie & Enzo
Both Bonnie and Enzo knew a lot of tragedy and faced some serious problems in life. That was one of the things that brought them together.
Bonnie wasn't very fond of Enzo at first, but he won her over in the end. Their relationship, unlike others on the show, wasn't as full of drama and danger. But even though it didn't have a happy ending, Bonnie and Enzo were happy while it lasted, and they seemed to be each other's genuine epic loves.
Klaus & Caroline
Unlike many of the other relationships in The Vampire Diaries, the will-they-won't-they dynamic between Klaus and Caroline never really went too far past that. However, that didn't stop this potential pairing from becoming one of the most popular ships in the history of the series.
The chemistry between them was off the charts, and although they never made things official, Klaroline had so many great scenes that they're undeniably one of the best romances in the show.
Stefan & Elena
Although Stefan and Elena didn't end up together and their initial attraction could potentially be explained by their dual doppelganger status, they were the relationship that truly launched The Vampire Diaries.
The love that they shared with each other was heartfelt, simple, and pure, and that made them appealing to audiences across the world. Elena may have ended up with Damon, but many fans were still rooting for Stefan and Elena to reunite up until the very end.
Damon & Elena
This was a sore spot for many fans of the show, but despite the way Damon had treated Elena at first, they still ended up together. He had many negative qualities, and some fans even thought Damon was irredeemable, but he tried to become a better man for Elena.
They separated during the show but got back together again after all was said and done. They started a family together once Damon became a human and lived happily ever after, according to the final episode of The Vampire Diaries. And regardless of any controversy, Delena was undeniably the most popular ship in the series.
The Worst Vampire Diaries Couples
Jeremy & Vicki
Jeremy genuinely liked Vicki, and although she seemed to have returned his feelings at one point, the relationship between them never worked. That was at least partially because Vicki hooked up with Jeremy in secret and didn't want anybody 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 do drugs with him and was a bad influence on the younger guy. Finally, she also tried to kill both Jeremy and his sister Elena once she became a vampire.
Damon & Andie
Damon's brief connection to Andie Star was essentially just a revamped version of his so-called "relationship" with Caroline. Sure, Andie said that she would have been with Damon even if he didn't compel her, but he didn't stop manipulating and controlling her regardless.
It seemed like Damon largely saw Andie as a useful tool and a way to kill time, and although Andie's untimely death indicated that maybe his feelings were a bit deeper, their relationship was gross.
Bonnie & Jeremy
Bonnie may have found her perfect partner in Enzo, but he wasn't her first boyfriend, not by a long shot. For quite some time, she and Jeremy dated. But their relationship had multiple issues, starting 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 got together only to break up later (usually because one of them temporarily died) and did this cycle several times before they called things off for good. Their relationship had a lot of drama, but it was never particularly interesting.
Tyler & 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 while Tyler was slightly nicer to Vicki in the following episodes, that's not saying much.
He still treated her as nothing more than a hook-up and acted ashamed to be with her, and their entire connection seemed designed as a hurdle that Jeremy and Vicki had to get over in order to start their own relationship anyway.
Damon & Caroline
Relatively early in the first season, Damon and Caroline had a very unhealthy relationship. Caroline was attracted to Damon, but he was only using her 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 Stefan luckily stopped. Although it seemed like they developed a strange frenemy-style relationship later on, they were indisputably one of the worst pairs in the show.
Katherine & Damon
Katherine seemed to have genuine feelings for both Stefan and Damon, and Damon clearly loved Katherine for years, but their relationship was pretty toxic. Katherine had very little affection for Damon and she preferred Stefan. Yet she led Damon on, let him believe she was trapped for over a century, and she didn't even bother to get in touch with him even though she was free the entire time.
Despite all this, Damon was still ready to forgive her once she came back but Katherine crushed him by saying that she had never loved him in the first place.
Caroline & Alaric
Considering the fact 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 from the fact Caroline had bafflingly given birth to Jo and Alaric's children thanks to a magical baby swap. However, even though they got engaged at one point, their relationship never felt like a real romance, and it was far more creepy than compelling.
