The Vampire Diaries wrapped up in 2017, but let’s be real, we’re all still emotionally recovering from some of those brutal breakups. For eight seasons, this supernatural drama gave us the kind of epic love stories that made us believe in forever, only to rip our hearts out and stomp on them repeatedly.
Between impossible circumstances, tragic deaths, and those cruel twists of fate, TVD proved it was a master class in making us ugly cry. Whether you’ve rewatched the series five times or you’re still avoiding certain episodes because they hurt too much, these breakups hit different. They’re the kind that make you pause and stare at the ceiling, questioning why you do this to yourself.
8. Matt and Elena’s Innocent Beginning (Season 1)
Matt and Elena’s breakup might not have been the most dramatic, but it represented something significant: the end of Elena’s normal life. These two had that sweet, innocent first-love energy that felt authentic and relatable. Matt represented Elena’s connection to her human world, while Stefan opened the door to the supernatural.
Their relationship ending was handled with remarkable maturity for a teen drama. There was no cheating, no betrayal, just the gentle acknowledgment that Elena had fallen for someone else. Zach Roerig played Matt’s heartbreak with such sincerity that you felt for this genuinely good guy who lost the girl through no fault of his own.
There's a difference @cwtvd @ninadobrev @zach_roerig @paulwesley @iansomerhalder #TheVampireDiaries #VampireDiaries #ElenaGilbert #MattDonovan #StefanSalvatore #DamonSalvatore pic.twitter.com/YVgXFuWfz3
— Angel0frage (@Angel0fRage25) February 25, 2020
What made this breakup significant was what it symbolized. Elena choosing Stefan over Matt was her choosing the supernatural over the mundane, excitement over safety, forever over temporary. It set the tone for Elena’s entire character arc and established Matt as the show’s moral compass: the guy who always put others first despite getting his heart broken.
Matt’s continued care for Elena throughout the series, even after she broke his heart, showed us what unconditional love looks like. Sometimes the saddest endings are the quiet ones that close doors we can never open again.
7. Alaric and Jenna’s Unfinished Story (Season 2)
In a show filled with supernatural chaos, Alaric and Jenna represented something precious: the possibility of normal, adult love. Their relationship was built on genuine affection, shared responsibility for Elena and Jeremy, and the kind of sweet, everyday moments that made you believe in happily ever after.
Watching Alaric integrate into the Gilbert family felt natural and right. He and Jenna had that comfortable, realistic chemistry that comes from two adults who’ve been through loss and are ready to build something stable together. Sara Canning and Matt Davis played their relationship with such warmth that you couldn’t help but root for them.
But TVD had other plans. Jenna’s death during Klaus’s sacrifice ritual didn’t just kill her, it destroyed the family unit they’d been building and left Alaric devastated. What made this particularly cruel was how close they were to making it official. Jenna had finally accepted the supernatural truth about her family, and they were ready to move forward together.
Their ending felt especially tragic because it represented the loss of hope for normalcy in the Gilbert family. Sometimes the quietest love stories leave the biggest holes when they’re gone.
6. Jeremy and Anna’s Star-Crossed Romance (Season 2)
First love hits different, especially when it’s tragic and supernatural. Jeremy Gilbert and Anna’s relationship was doomed from episode one. She was a 500-year-old vampire, and he was a grieving teenager trying to navigate his sister’s chaotic supernatural life. But somehow, their connection felt real despite the impossible circumstances.
Anna genuinely cared about Jeremy, protecting him while helping him understand the vampire world that had consumed his family. She could have easily used him for information about the tomb vampires, but instead, she fell for this sweet, lost kid who reminded her of her own humanity.
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When Anna died during the tomb vampire massacre, it marked Jeremy’s first real heartbreak and his entry into the supernatural world’s cruelty. Malese Jow and Steven R. McQueen had such natural chemistry that you believed in their love story, even knowing it couldn’t last.
The tragedy was compounded when Jeremy started seeing Anna’s ghost, unable to let go of what they had. It showed us how first loves leave permanent marks on our hearts, especially when they end too soon. Anna’s death also represented the loss of Jeremy’s innocence, forcing him to grow up way too fast.
5. Bonnie and Enzo’s Tragic End (Season 8)
This one hits different because Bonnie Bennett deserved the world, and for a brief moment, it looked like she was finally getting it. After seasons of being the friend who sacrificed everything for everyone else, Bonnie found someone who loved her unconditionally. Enzo St. John saw Bonnie’s worth when others overlooked her, and their connection was genuine and beautiful.
But TVD couldn’t let Bonnie be happy, could it? Instead of a breakup, we got something worse: Enzo’s death at Stefan’s hands while he was under Cade’s influence. Watching Bonnie hold Enzo as he died was absolutely heartbreaking. Kat Graham’s performance as Bonnie turned off her emotions to cope with losing the love of her life was raw and devastating.
🏆The vampire diaries/the originals best kiss awards 🏆
10) Bonnie and enzo first kiss 💌 pic.twitter.com/hlAfrRERPA
— The vampire diaries // The originals polls 🏆 (@originaIvampirs) January 20, 2018
What makes this particularly painful is that Bonnie had already sacrificed so much for her friends. She’d literally died multiple times, been trapped in prison worlds, and given up pieces of herself to save others. When she finally found happiness with Enzo, even that was taken away from her.
The injustice of it all still makes fans angry. Bonnie deserved her happily ever after, and losing Enzo felt like the universe was punishing her for daring to be happy.
4. Klaus and Caroline’s “Maybe Someday” (Season 5)
Okay, let’s talk about the ultimate “what could have been” relationship. Klaus and Caroline were never officially together, but their goodbye in Season 5 felt like losing the greatest love story that never got its chance to unfold. These two had everything: intense chemistry, genuine understanding, and the kind of connection that transcends species barriers.
Klaus Mikaelson, the Original Hybrid who terrified literally everyone, became vulnerable only around Caroline. She challenged him, called out his worst behaviors, and somehow saw potential for good in the monster everyone else feared. Meanwhile, Klaus brought out Caroline’s fire and made her feel special in ways no one else could.
When Klaus left for New Orleans, that scene with the drawing and his promise of “however long it takes” absolutely wrecked us. Joseph Morgan and Candice King had such incredible chemistry that you could feel the weight of their goodbye. Caroline’s tears, Klaus’s lingering look back, it captured everything tragic about timing and circumstances.
The worst part? They’re both immortal, so “forever” was actually possible for them. But duty, family obligations, and just plain bad timing kept them apart. Fans are still hoping for their reunion, and honestly, we don’t blame them.
3. Caroline and Tyler’s Long-Distance Demise (Season 6)
Sometimes the most realistic breakups hurt the worst, and Caroline and Tyler’s relationship ending felt painfully relatable despite all the supernatural drama. These two had such potential! They understood each other’s struggles with being supernatural creatures, they had genuine chemistry, and their relationship development felt organic.
But here’s the thing about Tyler: his obsession with revenge, particularly against Klaus, became more important than everything else, including Caroline. When he left Mystic Falls to break his sire bond and later to hunt Klaus, Caroline was left picking up the pieces of her life. The distance didn’t just separate them physically; they grew into completely different people with different priorities.
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What made this breakup so devastating wasn’t a dramatic scene or tragic death; it was the slow, painful realization that love sometimes isn’t enough. Tyler chose revenge over building a future with Caroline, and she eventually had to choose herself over waiting for someone who might never come back. Candice King played Caroline’s heartbreak beautifully, showing us how someone can be strong and vulnerable at the same time.
Their relationship became a casualty of Tyler’s inability to let go of his anger, and honestly, Caroline deserved so much better.
2. Damon and Elena’s Memory Wipe Heartbreak (Season 6)
If you thought Stefan’s sacrifice was brutal, buckle up because Damon and Elena’s situation was pure psychological torture. When Kai Parker (that psychotic little witch) linked Elena’s life to Bonnie’s with a sleeping spell, it created the ultimate Sophie’s Choice scenario. Damon had to choose between waking Elena (and killing Bonnie) or letting his soulmate sleep for potentially decades.
But here’s where it gets really twisted: Elena decided to have Alaric compel away all her memories of loving Damon before the spell took effect. Imagine watching the love of your life look at you like you’re a stranger, knowing they once loved you more than life itself.
Ian Somerhalder absolutely crushed this storyline, showing us Damon’s desperation as he tried everything to make Elena remember.
The scene where Elena tells Damon she doesn’t love him (with zero emotion, like she’s discussing the weather) still gives us chills. It’s the kind of cruel irony that only TVD could pull off. Your person is right there, but they’re completely gone. That’s some next-level heartbreak that still makes fans reach for the tissues.
1. Elena and Stefan’s Final Goodbye (Season 4)
Oh, this one still stings, doesn’t it? Stefan and Elena’s breakup wasn’t just the end of a relationship; it was watching the foundation of the entire series crumble before our eyes. When Elena transitioned into a vampire, everything changed. Suddenly, the sweet, human girl who fell for the brooding vampire was gone, replaced by someone whose very nature pulled her toward Damon instead.
What absolutely destroyed us wasn’t just that they broke up, but how Stefan handled it. This man (and we use that term loosely since he’s technically a 160-year-old vampire) showed us what true love looks like. He literally stepped aside and told Elena he wanted her to be happy, even if it meant watching her fall for his brother. Paul Wesley’s performance in that rain-soaked breakup scene was nothing short of phenomenal.
The worst part? You could see Stefan’s heart breaking in real-time, but he kept his composure because that’s just who Stefan Salvatore was. He set the bar impossibly high for fictional boyfriends everywhere, and honestly, we’re still not over it. Team Stefan fans felt this one in their souls.
| Rank | Couple | Seasons Active | Breakup Cause | Why It Still Hurts |
| 1 | Elena & Stefan | 1-4 | Personality change (Vampirism) | Foundation of the show crumbled |
| 2 | Damon & Elena | 1-6 | Memory compulsion / Sleeping spell | Soulmate forgot their love existed |
| 3 | Caroline & Tyler | 2-6 | Distance / Different priorities | Love wasn’t enough to overcome differences |
| 4 | Klaus & Caroline | 3-5 | Circumstances / Duty | Ultimate “what could have been” |
| 5 | Bonnie & Enzo | 7-8 | Death | Bonnie deserved her happiness |
| 6 | Jeremy & Anna | 1-2 | Death | First love tragedy |
| 7 | Alaric & Jenna | 1-2 | Death | Normal love destroyed by supernatural |
| 8 | Matt & Elena | 1 | Falling for someone else | End of innocence |
What made The Vampire Diaries’ breakups so effective was their emotional authenticity wrapped in supernatural circumstances. The show understood that when you’re dealing with immortal beings, the stakes for love and loss become infinitely higher. These weren’t just teenage breakups. They were epic love stories being torn apart by impossible choices, death, magic, and fundamental incompatibilities.
The series never took the easy way out with simple reconciliations or fairy-tale endings. Instead, it showed us that sometimes love isn’t enough, that good people don’t always get what they deserve, and that timing really is everything. Years later, fans still debate these relationships and mourn their endings because they felt real despite the fangs and magic.
Can’t get enough of Mystic Falls drama? All eight seasons of The Vampire Diaries are currently streaming on Netflix, Amazon Prime Video (with subscription), and available for purchase on Apple TV, Google Play, and Vudu.
Fair warning, though: Keep the tissues handy. These breakups hit just as hard on the rewatch, maybe even harder when you know what’s coming. Let us know your comments below on which one breaks your heart the most!
