The advent of The Vampire Diaries redefined the teen genre with its ability to weave fantasy and action with passionate romance. It reignited people’s interest in a well-crafted love triangle, but not all the love stories in the show ended with elation. While fans were always rooting for happy endings, some The Vampire Diaries couples had tragic arcs that didn’t end well.

Characters like Alaric and Stefan had some terrible luck with romances, often losing their partners in terrible ways or sacrificing themselves for the greater good of Mystic Falls. What made these calamitous romances even more devastating was that they all had the potential to be love stories that lasted forever, but fate had other plans.

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10 Alaric and Jenna

Jenna talks to Alaric excitedly in The Vampire Diaries

Alaric quickly became a permanent fixture in every season of The Vampire Diaries but had the worst luck with romance since the start. He had already lost his wife of 12 years, Isobel, to the allure of the supernatural. However, he got a new lease on life when he met Elena’s sweet and witty aunt, Jenna, and they began a relationship.

They had great chemistry and were warm and loving. Tragically, Jenna got caught up in Klaus’ games because she had not been told about vampires, werewolves, or the existence of any supernatural creatures by either Elena or Alaric. Klaus turned Jenna into a vampire, then promptly sacrificed her in front of her loved ones so he could break his curse and become a hybrid, leaving a hole in Alaric’s heart at the unexpected loss of another partner.

9 Silas and Amara

Silas holds Amara in The Vampire Diaries

Silas was one of the most menacing The Vampire Diaries villains, but his love story with Amara was a legendary one that lasted 2000 years. Amara and he got together secretly while Silas was still with Qetsiyah. They stole the potion for immortality themselves, and in her rage, Qetsiyah made Amara the anchor to the Other Side, entombing Silas after leading him to believe that Amara was dead.

Even when Silas learned that Amara was alive, they couldn’t be together in peace. Amara died as a human, while Silas passed to the Other Side. Their love was so great that it spawned generations of doppelgangers, but the two could never be together in peace because of how they had wronged Qetsiyah.

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8 Nora and Mary Louise

Nora and Mary Louise in TVD.

Despite being a part of the venomous Heretics led by Lily Salvatore, Nora and Mary Louise had a history that made audiences warm up to them instantly. Their love was forbidden, especially in the 1800s when they met each other. The Vampire Diaries couple faced opposition from the world for their sapphic love but stayed together through thick and thin.

They found acceptance in the modern day, but what divided them was ideological differences. Mary Louise chose to believe in Julian, while Nora knew that he had wronged Valerie by hurting her centuries ago. They could never truly be themselves and love proudly for most of their vampiric lives, and when they reached an era where they could, Nora and Mary Louise sacrificed themselves to destroy the Phoenix Stone.

7 Caroline and Stefan

Stefan and Caroline get married in The Vampire Diaries

Before falling in love, Caroline and Stefan had one of the best friendships in The Vampire Diaries. Slowly, Caroline fell in love with Stefan, who took a while to realize that his feelings had become romantic. They understood each other intimately but were torn apart when Stefan had Rayna’s target on his back and Caroline became pregnant with the Gemini twins.

In Season 8, Stefan proposed to Caroline, and they had a beautiful June wedding. In a heartbreaking twist, Stefan chose to sacrifice himself to kill Katherine and save Mystic Falls soon after. He had to save his brother, and Caroline had to let him go with a heavy heart almost immediately after they got married.

6 Matt and Penny

Matt stands with a gun while Penny flanks him in The Vampire Diaries

After years of being at the mercy of the vampires, Matt Donovan finally found true love and a purpose when he met Penny Ares. They were both on the police force, so they identified with each other, and Matt opened up to her about the supernatural and what lurked in the dark. Sadly, his obsession with hunting down vampires led to the end of their relationship.

One night, as Matt was hunting down Stefan, he shot blindly in the dark and ended up shooting Penny fatally. Stefan compelled Matt to forget this because of the enormity of this mistake, but he later remembered that he had killed his own fiancée. This was a cruel twist in Matt’s life, especially since he had never had a great family life since childhood.

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5 Alaric and Jo

Alaric and Jo get married in The Vampire Diaries

Sweet and sensitive Jo brought out the best in Alaric, which was why they decided to get married. Jo had a melancholic past where she had almost been killed by her own brother Kai in the Gemini coven, but she was ready to start fresh with Alaric. On her wedding day, Kai concocted a devious plan where he stabbed his sister lethally and endangered her twins.

It was gut-wrenching to see a gentle soul like Jo die on her wedding day. In his grief, Alaric tried numerous crooked ways to bring her back to life but only ended up disrespecting her memory. Their family life was snatched from them for no good reason.

4 Bonnie and Enzo

Enzo and Bonnie embrace in The Vampire Diaries.

After a string of unsuccessful relationships, Bonnie found her soulmate in Enzo. Unlike other couples, Bonnie and Enzo even made their peace with the fact that Bonnie was a witch and he was a vampire. This meant that they were mature enough to respect each other’s choices and accept that they may have different life spans.

After three years of protecting Bonnie and their relationship, Enzo was ready to commit to her. After a cursed life, it was heartening to see Enzo also find true love. However, Stefan killed Enzo on a no-humanity spree, which left Bonnie all alone again. There was no actual reason to eliminate Enzo from the show, which was why many fans felt that this arc was unfair to the couple.

3 Rebekah and Stefan

Rebekah and Stefan in the Twenties in The Vampire DIaries

The Original sister and Stefan met during the Prohibition era, and their relationship was flirty. Stefan was living a life of vampiric hedonism, but after a while, he and Rebekah fell in love. Stefan even met Rebekah’s brother, Klaus, but their camaraderie turned sour when Mikael descended upon the Originals.

Klaus asked Rebekah to choose between him and Stefan, and when Rebekah chose the latter, he stabbed her with a White Oak dagger and locked her away. Stefan was compelled to forget all about them, which meant that Klaus effectively erased their whole relationship without their knowledge. This was heartbreaking to see, especially since all Rebekah wanted was to find someone who cherished and loved her.

RELATED: 10 Most Important Stefan and Elena Episodes in The Vampire Diaries

2 Stefan and Valerie

Stefan and Valerie sit at a distance and talk in The Vampire Diaries

Many fans thought that Katherine was Stefan’s first love, but it was actually Heretic Valerie who stole his heart when he was still human. They had met at a town fair and had spent some time getting to know each other. Stefan also had sex for the first time with her, which made her truly special for him.

Valerie had promised to meet Stefan so that they could run away together, but Julian cut their love story short. He found out that Valerie was pregnant, so he beat her till she lost her child and couldn’t return to Stefan. The truth only emerged when Valerie met Stefan after years, and even when they rekindled their romance, she realized that they missed their chance way back in 1863.

1 Damon and Rose

Damon hugs Rose in a field in The Vampire Diaries

Damon was helplessly in love with Elena, who was loyal to his brother. The only person who could make Damon move on and experience joy for himself was Rose, but she did not survive for long. Initially, Rose had kidnapped Elena to turn her over to Elijah, but when she found out what Klaus wanted, Rose defected to the side of the Salvatores.

Damon and Rose began a romantic relationship grounded in respect, tenderness, and empathy. They were compatible in every way possible, but Rose got bitten by a werewolf. At the time, Damon did not know how to cure her, so she passed in peace, with Damon guiding her last moments through telepathy.

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