All teen dramas, especially the supernatural ones, come with their fair share of tragedy, and The Vampire Diaries is no different. Elena Gilbert was going through a difficult time during the show's pilot, as she and her little brother were attempting to grieve the death of their parents and were adjusting to life with their Aunt Jenna.
Her luck gets even worse when Elena turns out to be a Petrova Doppelganger, and all of her friends are pulled into a world that's feels impossible to get out of alive. The Vampire Diaries isn't afraid to kill off fan-favorite characters, and because of the violent nature of the show, many episodes can get heavy and heartbreaking.
10 Season 5 Episode 11: "500 Years Of Solitude"
In the 100th episode of the series, several beloved characters returned to say goodbye to Katherine Pierce. However, some had more pure intentions than others. After Elena forced Katherine to take the cure, centuries began to catch up to her, and she was left dying of old age.
Stefan is kind to Katherine in her final moments, and when she is forced to relive the murder of her family, he enters Katherine's dreams and makes sure she can go peacefully. But Katherine never planned to go anywhere and she jumps into Elena's body moments before her own death.
9 Season 1 Episode 14: "Fool Me Once"
Damon always had a villainous streak, but as Elena said herself, he truly believed that every move he made was for love. He forces Bonnie and her grandmother to open the tomb to save Katherine, but is heartbroken to discover that she was never there.
His devastation is difficult to watch, but the real tragedy doesn't happen until later that night. After using too much power to keep the tomb open, Bonnie finds her grams dead in her room.
8 Season 2 Episode 21: "The Sun Also Rises"
"The Sun Also Rises" had one of the highest death rates of the series, but there was one that stood out above the rest. Elena and Jeremy's Aunt Jenna was one of the only characters in the show still oblivious to the vampires lurking around Mystic Falls.
She dedicated her life to taking care of her sister's kids after she passed away, but Jenna realized in her final moments that they were the ones protecting her. When Klaus needs to sacrifice a vampire to lift his curse, he cruelly uses Jenna in the sacrifice.
7 Season 2 Episode 22: "As I Lay Dying"
After Damon suffers from a lethal werewolf bite, he decides to accept his fate and go quietly. Stefan has to lock his brother in the basement to prevent him from taking off his daylight ring in the sun. Damon relives some of his worst mistakes during the episode, and he apologizes for them during an emotional scene on his death bed.
But Stefan comes through with a cure and Damon is healed right in the nick of time. To pay for the cure, Stefan is forced to leave his brother and Elena, and travel the country making hybrids with Klaus.
6 Season 6 Episode 14: "Stay"
Caroline has always been a bright light in a dark world, and she remains an optimist even when there's no reason to hold out hope.
Caroline went through the wringer throughout the series, but nothing broke her like losing her mother did. Out of all the ways to die in the vampire-filled world, cancer felt like an especially cruel way to go. After Caroline, Liz's death affected Damon the most, as Liz had come to see Damon as her best friend.
5 Season 8 Episode 11: "You Made A Choice To Be Good"
The Vampire Diaries refuses to let Bonnie Bennett be happy. She's constantly treated like an object by the other characters and is ignored until they need her to do a spell and fix their problems. For the first time in the show's history, Bonnie finally had someone who cared about her above all else.
Enzo and Bonnie were arguably the best couple in the series, and it seemed as though Bonnie might get the happy ending she deserved. But moments before Bonnie and Enzo ride off into the sunset, a humanity-free Stefan kills him right in front of Bonnie's eyes.
4 Season 3 Episode 22: "The Departed"
Elena's death was the show's most shocking twist. Rebekah drives Elena and Matt off the road and into the water, paralleling Elena's accident with her parents. As Elena tries to escape, the show flashes back to her parents' death in a scene designed to bring viewers to tears.
Stefan attempts to save Elena as he did in the past, but Elena begs him to save Matt instead. Stefan respects her wishes, and by the time he comes back for Elena, she has already drowned. Little did anyone know, that Meredith had given Elena vampire blood when she was in the hospital earlier that day.
3 Season 5 Episode 22: "Home"
It was hard for fans to fully believe that The Vampire Diaries killed off Damon Salvatore and Bonnie Bennett, but it didn't make the episode any less heartbreaking to watch.
Bonnie sacrifices herself for the greater good, as usual, and Damon gets stuck on the other side and unable to make it back to Elena. Although she can't see him, Elena breaks down and begs Damon not to leave her. The final shot of the season includes Bonnie and Damon holding hands and preparing themselves for whatever comes next.
2 Season 6 Episode 22: "I'm Thinking Of You All The While"
When Nina Dobrev chose to leave the series after the sixth season, The Vampire Diaries had to find a way to write off her character. It wouldn't make sense for Elena to leave her friends, but killing her would prevent Elena and Damon from having their "happily ever after" in the series finale.
The show chose to put Elena in a Sleeping-Beauty-type slumber that she could only wake up from after Bonnie had died. Every character has a chance to say an emotional goodbye before Elena is sealed in a coffin.
1 Season 8 Episode 16: "I Was Feeling Epic"
Even viewers who had stopped watching the show over the years were impacted by the series finale. Stefan injects Damon with the cure and sacrifices himself to save Mystic Falls. He reunites with Elena as he heads to the afterlife, and the two share a heartbreaking goodbye.
Stefan's friends and family are seen mourning him in the future, but Damon is affected most of all. A flash-forward reveals that Damon and Elena make it to the after-life, and Damon and Stefan have a teary reunion during the show's final shot.
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