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 on 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 us just how great romance could be, others provided a cautionary tale in what not to do when coupling up. In this list we’re exploring the different couples from The Vampire Diaries and putting them in order from worst to best.
Here are 25 Vampire Diaries Couples Ranked (And How Long They Lasted).
25 TYLER AND VICKI (A FEW MONTHS ON AND OFF)
Vicki and Tyler started dating 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.
24 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.
23 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.
22 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.
21 ALARIC AND CAROLINE (1-3 YEARS)
Alaric and Caroline were a very unexpected pairing. 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 is still in love with Stefan, he broke it off, but they continue to be very involved in each other's lives because of their children.
20 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 spent 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.
19 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 good-bye.
18 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 with child. 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.
17 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 on 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.
16 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.
15 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.
14 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 come up in Mystic Falls. Anna decided to leave Jeremy alone when she realized she was holding him back from the living.
13 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.
12 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.
11 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.
10 TYLER AND LIV (ABOUT 5 MONTHS)
Tyler and Liv were fellow students at Whitmore College. They had feelings for each other, although Liv was reluctant to act on them. Still, they eventually succumbed to their attraction and started a relationship. Their time together was challenging because it coincided with Liv's obligations to her family's coven of witches.
Tyler was determined to protect Liv any way he could and did his best to keep her safe. Ultimately, when Liv's twin Luke meets his demise at the hand of their older brother Kai, Liv decided to go after Kai. When this almost led to Liv's demise, Tyler broke up with her. Months later when Kai tried to end her family at her older sister's wedding, Liv asked a mortally wounded Tyler to take her life so he could re-trigger his werewolf curse and the superior healing that went with it. So, ultimately, she sacrificed her life to save his.
9 STEFAN AND REBEKAH (A FEW MONTHS)
Rebekah and Stefan first met in Chicago in 1922. Stefan and Rebekah started a romance and Stefan became friends with Rebekah’s brother Klaus. At the time, Stefan still embraced the vampire lifestyle, so he and Rebekah saw the world similarly.
Their romance had a fun and playful quality, that eventually led to the pair falling in love. Unfortunately, things couldn’t last. Klaus and Rebekah’s father soon tracked his children down. He wanted to eradicate them because he turned them into vampires. Rebekah wanted to flee with Stefan, but Klaus wouldn’t allow it. When Rebekah tried to run with Stefan instead of Klaus, Klaus neutralized her and used compulsion to remove any memory of Rebekah or him from Stefan’s mind.
8 BONNIE AND JEREMY (FIRST TIME: 4-5 MONTHS; SECOND TIME: ABOUT 6 MONTHS)
Bonnie and Jeremy grew up together. To Bonnie, Jeremy was her best friend Elena's younger brother. When they were both in high school, they started to hang out more and soon developed feelings for one another. Things progressed slowly at first. Bonnie was especially resistant to the relationship. They ended up dating but for a great deal of that time, Jeremy was emotionally turning on Bonnie with the ghosts of his ex-girlfriends, Vicki and Anna.
After breaking up, Bonnie and Jeremy slowly grew close again and began their relationship anew. This time, they were fully committed to each other and in love. Their romance was cut short when Bonnie was pulled into a magical prison world that separated her from Jeremy.
7 STEFAN AND ELENA (2 YEARS, ON AND OFF)
Stefan first met Elena when he saved her life after her parents’ car went off Wickery bridge. After realizing that she looked exactly like his ex-girlfriend, Katherine, Stefan decided to stick around Mystic Falls to observe Elena. Eventually, he realized what a good person she was and decided he needed to get to know her. That started off the couple’s love story, which for a time was the central romance of The Vampire Diaries.
Stefan and Elena fell head over heels in love and could be very sweet and supportive of each other. Yet, his status as a vampire and hers as the doppelganger put them in constant danger. They frequently broke up in an effort to keep each other and the people they cared about safe, but then came back to each other despite knowing better.
6 CAROLINE AND TYLER (A LITTLE OVER A YEAR, MOSTLY APART)
Caroline and Tyler had known each other since childhood but were never friends. However, after Caroline became a vampire, she learned about the supernatural. So she was the first to recognize when Tyler activated his werewolf curse. She supported him through his transition, and he started to develop feelings for her.
She was still in love with Matt at the time, but once they broke up, she started a romance with Tyler. The couple never got much of a chance though. Tyler became a vampire/werewolf hybrid sired to Klaus. When he realized how much of his free will had been taken away, he left town to break the sire bond. When he returned, Klaus threatened him, forcing Tyler to go on the run. Once Klaus ended his vendetta against Tyler, though, Tyler chose to go after Klaus instead of being with Caroline, officially ending their relationship.
5 ALARIC AND JENNA (ABOUT 4 MONTHS)
Alaric met Jenna, Elena and Jeremy's maternal aunt, soon after he came to Mystic Falls. The two bonded, grew close, and finally started dating. Things seemed to progress quickly as Alaric regularly slept over at her house.
The romance became strained when John Gilbert, Elena and Jeremy's paternal uncle, came to town and questioned how truthful Alaric was being with Jenna and if he was truly over his deceased wife. When she learned about vampires, Jenna broke up with Alaric, feeling betrayed that he kept secrets from her. Soon, she forgave him, and they made up. The reconciliation was short-lived, though. Klaus turned Jenna into a vampire and sacrificed her in a ritual before Alaric was able to rescue her.
4 STEFAN AND CAROLINE (FIRST TIME: ABOUT 2 YEARS; SECOND TIME: ABOUT 6 MONTHS)
Stefan and Caroline were friends for years. Over time, they became one another's support systems and developed romantic feelings for each other. However, their timing always seemed to be off and it took them a long time to get together. They finally managed to make a relationship work for a couple of years but were driven apart when Stefan was marked by the vampire hunter Rayna Cruz and forced to go on the run.
After three years in which they were both with other people, they got back together. Not wanting to waste any more time, Stefan proposed soon afterwards. They were again driven apart when Stefan was forced to turn off his humanity and work for Cade, aka The Devil. Once he got his humanity back, the pair finally got married. Unfortunately, Caroline soon became a widow when Stefan sacrificed himself to save Mystic Falls.
3 NORA AND MARY LOUISE (136 YEARS)
Nora and Mary Louise are the pairing with the most longevity on this list – after all, not many couples can say they celebrated a centennial. The pair started dating in the late 1880s when their romance would have been forbidden. Despite that, they managed to sustain their relationship for an impressive amount of time. They weren't especially nice to others, but they clearly cared deeply for each other.
Realizing that their relationship was more accepted in modern times, they got engaged. Even though they briefly broke up over a disagreement among their Heretic clan, they quickly forgave each other. Their love story came to a sad end when the two decided to sacrifice their lives in order to destroy the weapons of the vampire hunter, Rayna Cruz.
2 ALARIC AND JO (ALMOST A YEAR)
Jo is the love of Alaric's life. She was born into a witch coven but decided not to practice magic as an adult. Instead, she became a doctor and taught at Whitmore College. She and Alaric met while chaperoning a college party there. While their first encounters were awkward, Jo was clearly attracted to Alaric and they soon started to date.
After a few months, Jo became with child and Alaric asked her to marry him. At their wedding, Kai, Jo's twin, takes her life and the lives of her unborn twin girls just as she is beginning her vows. This left Alaric bereft and determined to find a way to bring Jo back to life.
1 BONNIE AND ENZO (ABOUT 3 YEARS)
Bonnie and Enzo weren't the most obvious pairing. However, once Enzo decided he needed to keep Bonnie safe from the supernatural organization, the Armory, they slowly grew close. Their feelings eventually became romantic. They both were completely invested in their relationship and loved each other completely.
After an extended period of time together, they were forced apart when the siren Sybil used mind control to make him come with her and do her bidding. Eventually Bonnie got him back, but Stefan ended Enzo's life shortly afterward. Bonnie was so devastated by the loss, that she created a new afterlife for his soul. Enzo continues to watch over Bonnie as she fulfills her promise to him to live her life to the fullest.