CW's The Vampire Diaries is brimming with romance. While the love triangle between Stefan, Elena, and Damon made up the core of the show, Stefan/Elena and Damon/Elena were far from the only couples to attract fan love. In fact, throughout the show's eight seasons, each character had their fair share of relationships. This resulted in dozens of couples, all of whom had their own shippers.
Yet, each of the relationships in The Vampire Diaries wasn’t equally successful. And while the characters committed wholeheartedly to those couplings, the length of time they stayed together was highly variable. Plus, the consequences of some relationships reverberated years later, even if the couples themselves only lasted weeks. Meanwhile, other relationships were quickly forgotten as each participant moved on to greener pastures. No matter how epic or broken their previous relationships were, the characters of The Vampire Diaries were always eager to try again – sometimes even with the same person. As a result, the quality of different couples’ romances could vary greatly. So, while some characters' relationships showed the audience just how great romance could be, others provided a cautionary tale of what not to do when coupling up.
Updated on June 20th, 2022 by Amanda Bruce: Nearly a decade on television means a lot of different relationships in a show like The Vampire Diaries. Add to that spin-off series The Originals and Legacies set in the same universe where fan-favorite characters could be revisited, and there is so much lore and so many relationships for fans to invest in. As Legacies comes to an end and The Vampire Diaries universe seems to be put to bed, however, fans will simply have to revisit these characters and pairings on streaming sites instead.
DAMON AND CAROLINE (A FEW MONTHS)
Both of these characters are incredibly loved by the audience because of their complexities, and they provided for one of the earliest relationships in The Vampire Diaries. At the time that they were together, however, Damon was largely an antagonist and Caroline was his victim. While she was still human, she was compelled into providing him information about others in town, and that compulsion led to a relationship that she hid from her friends.
Damon even used her as a food source before she was turned into a vampire and spending time in his bed. That's not exactly the makings of a healthy relationship, and it's amazing that the writers were able to have them become eventual allies, even family, as the series continued.
TYLER AND VICKI (A FEW MONTHS ON AND OFF)
Vicki and Tyler started their relationship at some point before The Vampire Diaries started. It was a tumultuous relationship and they broke up. But when the school year began, they got back together again. Even though they were physically attracted to each other, neither was truly emotionally invested in their relationship. Tyler, in particular, did not treat Vicki well. He was embarrassed to be seen with her because of her family background. And when she was hospitalized, he didn't visit her.
Vicki felt she should be with Tyler because he was her age and she was comfortable with their arrangement. However, Jeremy opened her eyes to the idea that she might deserve better.
DAMON AND KATHERINE (2-3 WEEKS)
Katherine is the vampire who turned Damon and Stefan. She met the brothers when she came to Mystic Falls in 1864. She took up residence at the Salvatore home and quickly turned her attention to romancing both of them.
During their brief time together, Damon fell deeply in love with Katherine. He continued to hold a torch for her for over a hundred years after he learned that she hadn’t actually burned in Fell’s Church, as he’d been led to believe. While Katherine never really returned his feelings, Damon spent decades attempting to free her from the church and idealizing her in his mind. This led to an especially rude awakening when Katherine eventually did return to Mystic Falls.
STEFAN AND KATHERINE (2-3 WEEKS)
Katherine went for Stefan at the same time she did Damon. Yet, while Stefan was smitten with Katherine, his feelings for her didn't seem to develop quite as deeply as Damon’s did. In fact, Katherine appeared to care more for Stefan than vice versa.
Unlike Damon, he never discovered that Katherine managed to escape her demise in Fell's Church. Instead, Stefan learned to enjoy being a vampire and moved on from Katherine after his transition. So when Katherine eventually came back into the brothers’ lives, Stefan was able to see her for the manipulative and selfish individual she was.
BONNIE AND JAMIE (A FEW DAYS)
Bonnie and Jamie had a lot of potential to be a great pairing. He was sweet, and he took the existence of vampires, werewolves, and witches in stride. Jamie also happened to be the one guy Bonnie dated in the show who was completely human and didn't end up dead after being caught up in the happenings of Mystic Falls.
The trouble is that Jamie was essentially family. Bonnie met him while searching for her mother, and it turned out Jamie had been taken in by her mother like a son. Though the two hit it off right away, it's a big leap for the audience to think of Abby Bennet's children dating. It didn't help that he vanished from the show with no explanation as to whether they decided to remain friends or even keep in touch.
KATHERINE AND ELIJAH (3 MONTHS OR SO)
Katherine and Elijah first met in 1492 when Katherine was still human. Elijah's brother Klaus had plans to sacrifice Katherine as part of a ritual, but Elijah, having fallen in love with Katherine, was making plans to save her. Instead, Katherine took matters into her own hands and turned herself into a vampire. For the next 500 years, Elijah helped Klaus pursue Katherine for betraying him.
When Elijah finally sees Katherine again in the present day, the encounter is hostile. Eventually, though, the two started a relationship when Katherine takes up residence in a small Pennsylvania town. Soon, Elijah starts to doubt her feelings for him, though. He worries that Katherine simply sees him as a means to an end. Katherine denies that's the case, but Elijah doesn't trust her and ends the relationship.
ALARIC AND CAROLINE (1-3 YEARS)
Alaric and Caroline were a very unexpected The Vampire Diaries couple. Alaric was Caroline's history teacher when Caroline was still in high school. When Alaric's fiancée's life ended (while she was with children), her twin infants were magically transferred into Caroline and she carried the babies to term. In that time, she became deeply invested in the girls and, when they were born, embraced the role of their mother.
Over time, she and Alaric grew closer. Eventually, Alaric fell in love with Caroline and the pair got engaged. While Caroline didn't return Alaric's feelings, she agreed to marry him for the sake of their daughters. When Alaric realized that Caroline was still in love with Stefan, he broke it off, but they continued to be very involved in each other's lives because of their children.
REBEKAH AND MATT (3 Months)
Matt, the only character on The Vampire Diaries who remained human throughout the show, was generally against vampires. Despite that, Rebekah developed feelings for him and attempted to woo him by inviting him to parties and buying him expensive gifts. None of that worked, but when she took the time to get to know him and helped him study, he started to warm up to her.
Since he had no plans after graduating from high school, he agreed to travel the world with her for the summer, on the conditions that she didn't turn him into a vampire and what happened on the road stayed there. During their travels, they had a romantic relationship, but it ended when Rebekah moved to New Orleans to be with her brothers.
CAROLINE AND JESSE (A FEW WEEKS)
Caroline and Jesse met in college while Caroline was trying to live a normal life despite being a vampire. Jesse was one of the few people to call her out on her weird behavior. At the time, Caroline was in a long-distance relationship with someone else, but there was clearly a spark between the two.
Just as they became friends and had the potential for something more, however, Jesse was turned into a vampire with Caroline's blood in his system because she tried to save his life. Jesse became the subject of an experiment as a vampire that fed on other vampires, and Elena found herself forced to kill him in a confrontation. As a result, they're one of the shortest relationships in The Vampire Diaries. The audience doesn't get a lot of time with the two of them and doesn't know how their relationship would have progressed once Jesse knew the truth about everything.
ALARIC AND MEREDITH (ABOUT A MONTH)
Alaric and Meredith met at the local hospital. He was hit by a car and she was his doctor. Afterward, he kept running into her. When Meredith revealed her knowledge of vampires, the pair started to bond. They had a light, flirtatious chemistry that made them a fun couple.
Unfortunately, there was also someone ending people's lives in town – and both Meredith and Alaric were suspicious that the other was the culprit. Ultimately, Meredith was proven correct. Alaric had developed a dangerous alter-ego he knew nothing about. His alter-ego agreed to be turned into a vampire, but when Alaric discovered what happened, he decided to forego his transition and away instead. Meredith gave him a sedative to make his end easier and said goodbye.
