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 pass away instead. Meredith gave him a sedative to make his end easier and said goodbye.
JOHN AND ISOBEL (A FEW MONTHS)
John and Isobel dated when they were teenagers in high school. John fell in love with Isobel, but Isobel didn’t return his feelings. However, Isobel ended up pregnant. Not knowing what else to do, John took her to his older brother, who was a doctor, to deliver the baby. The new parents agreed to give the baby up to John’s brother and his wife.
Ultimately, Isobel married someone else, but John and Isobel still kept in touch over the years. It was John that put Isobel in touch with Damon when she wanted to talk to a vampire. They also teamed up to make sure their daughter, Elena, stayed safe, even though she was unaware that they were her biological parents.
ALARIC AND ISOBEL (ABOUT 12 YEARS)
Isobel met Alaric while she was studying parapsychology and folklore at Duke. She learned about vampires from John Gilbert as a teenager and had researched the supernatural ever since. Of course, to the University and Alaric, this just seemed like a legitimate line of academic inquiry.
When Alaric was initially introduced in The Vampire Diaries, he believed that Isobel had met her end at the hands of a vampire. He had learned how to hunt and take them out in order to exact revenge for his wife. Given Alaric’s continued devotion to Isobel, it would seem much of the pair’s marriage was positive. At some point in their relationship, though, Isobel became more interested in the idea of being a vampire than being with Alaric. Unbeknownst to him, the vampire he saw feed on her didn’t take her life, instead, he turned her. When Isobel made the transition, she started a new life without Alaric.
SILAS AND AMARA (OVER 2,000 YEARS, ON AND OFF)
Without Silas and Amara, there would be no doppelgängers in The Vampire Diaries. In fact, without their original immortal relationship, many of the relationships in the show would likely never have come to pass.
Originally, Silas was in a relationship with Qetsiyah, a powerful Traveler, but he fell in love with her handmaiden Amara. He devised a plan to use Qetsiyah's potion for immortality so that he could be with Amara forever, but Amara was taken by Qetsiyah and held for 2,000 years while Silas was trapped. Though the two deeply loved one another, Amara chose to take the cure and become human once she was woken up by Silas, apologizing to him. For Silas' part, he loved her so much that he was willing to respect her wishes and let her go, even allowing himself to be killed and trapped on The Other Side so that she could die as a human and move on.
JEREMY AND VICKI (3-4 Months)
Jeremy and Vicki traveled in the same questionable circles and during the summer break between school years, they started an intimate relationship. Vicki was older than Jeremy, though, and thought she'd be judged for being with someone younger. So, she demanded they keep their relationship a secret.
Vicki got back together with Tyler when the school year started, but Jeremy still harbored feelings for her. He repeatedly told Vicki that being with Tyler was a mistake. Eventually, Vicki realized Jeremy was right about Tyler and picked up with Jeremy again. Soon afterward, Vicki became a vampire and was quickly staked after she tried to bite Jeremy, leaving him distraught.
CAROLINE AND KLAUS (An Afternoon)
Caroline and Klaus have a complicated relationship. It started on purely antagonistic terms, but soon Klaus came to admire Caroline. He realized she was smart and spirited and made his feelings known. Caroline couldn't overlook his past, though, and refused to acknowledge the spark between them.
When he left Mystic Falls for New Orleans, Klaus informed Caroline that someday he wanted to show her the world and that he intended to be her last love. When he briefly returned to town, he promised never to come back if she'd be honest about her feelings for him. For the first time, she admitted her attraction and the pair were intimate, but Klaus left soon afterward. They saw one another on several additional occasions but only as friends.
ELENA AND MATT (APPROXIMATELY 3 YEARS)
Exactly how long Elena and Matt were together is left ambiguous in The Vampire Diaries. The characters mention them dating for most of high school before Elena meets Stefan and Damon Salvatore, though they do seem estranged for some of that time. Matt is the most drama-free of Elena's love interests.
He genuinely cares about her and wants her to be happy, but as she pulls away from him, he becomes more and more confused about the state of their relationship. Watching them fall apart is tough, but their history allows the two to maintain a friendship, even as Matt comes to loath all of the supernatural elements of Mystic Falls.
JEREMY AND ANNA (ALMOST 3 MONTHS)
Jeremy and Anna initially entered each other's lives under false pretenses. Anna was a vampire and she wanted to use Jeremy's blood to resurrect her mother, also a vampire, who had been trapped in a tomb for over a hundred years. Meanwhile, Jeremy wanted Anna to turn him into a vampire so he could be with Vicki, who he was unaware was gone.
When the truth came out, they reconciled and started a real relationship, which unfortunately ended with Anna's demise. Later, Jeremy learned he could see ghosts, including Anna. So, Anna and Jeremy spent time together and she helped him with the supernatural problems that inevitably came up in Mystic Falls. Anna decided to leave Jeremy alone when she realized she was holding him back from the living.
CAROLINE AND MATT (ABOUT 5 MONTHS)
Caroline and Matt had known each other since they were children and, throughout most of that time, Matt didn't like Caroline very much. Once they started talking and sharing their problems in high school, though, they realized they had a lot in common and soon got together. However, they had some problems, especially since Caroline was often jealous of Matt's history with her best friend Elena.
Caroline broke up with Matt after she became a vampire, but they briefly got back together after Caroline made a grand gesture and declared her feelings for him. When he learned Caroline was a vampire, though, Matt decided he couldn't be with Caroline, leading to the permanent end of their relationship.
DAMON AND ELENA (DECADES)
While Elena fell in love with Damon’s brother first, it was Damon that she ultimately ended up with. She was clearly attracted to Damon, but throughout the time she dated Stefan, she stayed loyal to Stefan. When she was turned into a vampire with Damon’s blood, though, she and Damon started a relationship. Initially, everyone believed their romance was the result of Elena’s sire bond with Damon. Even after it was broken, however, Elena chose Damon over Stefan.
Damon often did the wrong thing, but he attempted to keep his more questionable tendencies in check for Elena’s sake. And Elena was more than willing to call him on it when he didn’t live up to her expectations. Sometimes this caused friction, but Elena and Damon had a passion that neither could deny. Each of them would do almost anything to be with the other. By the end of The Vampire Diaries, they both took the cure for vampirism and were living out their human lives together.
STEFAN AND VALERIE (A NIGHT IN 1863, 3 YEARS IN MODERN DAY)
Valerie was Stefan's first love. The pair met when Lily, Stefan's mother who he believed had passed away, sent Valerie to check on Stefan in 1863. At the time they were both still human. They spent the day together at a fair. Even though Julian, Lily's lover, attempted to keep them apart, that brief time resulted in Valerie carrying a child. She told Stefan she would return to run away with him but before she could, Julian learned about the child and harmed her, causing her to lose it.
After about 150 years, the pair met again after both becoming vampires. Initially, they were just acquaintances, but then they became friends and allies. Eventually, they rekindled a romance that lasted for three years. However, when Valerie realized that Stefan still had feelings for his ex, Caroline, she broke up with him.