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  • The final minutes of "Fool Me Once", from the moment Damon finds out Katherine faked her own death, to the scene where Bonnie finds her grandmother dead.
  • In the finale, Anna's death.
  • Stefan comforting Caroline during her breakdown over killing her first victim.
  • Caroline compelling her mother to forget their make up, because she couldn't risk her knowing about vampires.
  • In "Rose", Damon's I Want My Beloved to Be Happy moment, confessing his love for Elena and then compelling her to forget it so that it won't ruin things for her and Stefan.
    • Even most Stelena fans still found this scene touching and heartwarming.
  • "Katerina" shows the start of Katherine's descent into darkness. It was full of tearjerking moments, and portrayed Katherine (who previously had been seen as a Magnificent Bitch teetering into Complete Monster) surprisingly sympathetically.
  • Tyler's werewolf transformation. The pain that he went through was heartbreaking
  • Roses's death
    • Damon having a break down after Rose's death.
  • Elena breaking down and confessing to Stefan that she doesn't want to be a vampire.
  • Jenna and John's deaths, especially John's letter to Elena read over the funeral montage. Even if you hated the guy, he sacrificed himself for his daughter.
  • Damon telling Stefan that he's been bitten by a werewolf. Stefan's expression is as heartbreaking as Damon's resignation.
  • In the season finale: Damon dying. Eeven though we knew he would survive in the end, it was still tragic to hear him tell Elena he loved her and to apologize to Stefan - who, meanwhile was out sacrificing himself to Klaus to save his brother.
  • In the season 3 opener "The Birthday", the phone call between Stefan and Elena made even die-hard Delena fans tear up.
  • In "The Birthday", when Elena gets up and throws the curtains open, seeing how she has to steel herself before doing that and the fact that it's almost certainly been that way every morning since Stefan disappeared is heartbreaking.
  • Klaus compelling Stefan to switch off his humanity while Elena watches in horror. At first Stefan fights the compulsion of an Original, but inevitably, it works.
  • Anna finding her mum again in "Ghost World.
  • The Original family's story itself is a Tearjerker, especially considering the fact that Mikael and Esther only turned their children so they could protect them from the werewolves, after their youngest son's tragic death. And then they all die and scatter.
  • The end of "Ordinary People", with Rebekah breaking down sobbing after learning that Klaus killed her mother.
  • YMMV but something about Elena telling Damon they have to let Stefan go is heart wrenching.
  • Caroline having to slowly watch her father die when he refuses to drink blood to complete the transition.
  • Damon's attempted Suicide by Sunlight, especially when one remembers his asking Elena to forgive him, her refusing, and his telling her to take all the time she needs - all the time knowing that he will die soon and keeping it from Elena.
  • When Alaric refuses to complete the transition, and everyone comes to say goodbye to him. Subverted later when a possessed Bonnie feeds him her blood, turning him into a vampire hunter
  • Rebekah breaking down when Alaric stakes Klaus right in front of her.
  • Damon's goodbye to Elena as she and Matt drive back to Mystic Falls. Sobbing, she tells him that she's never fallen out of love with Stefan and that maybe if they'd met first... And then It Gets Worse. Damon actually did meet Elena first on the night her parents died. And he compelled her to forget about it.
  • Seeing Elena's final moments with her dad during the car crash and the parallels to it when she sacrifices herself so Stefan can save Matt, like her dad did with Stefan.
  • Caroline and Tyler's tearful goodbye after they find out about Klaus' death. And Tyler making Caroline promise to tell his mother that he got out of town like he said he would.
    • Possibly subverted, since it remains to be established whether that was really Klaus possessing Tyler rather than Tyler himself.
  • Damon cradling Alaric as he dies. His stricken mantra of 'You can't be dead, you can't be dead,' and you know he's thinking about Elena
    • Though he's probably thinking about his only friend as well. In that moment he thinks he's lost them both.
  • When the ghost of Alaric - the real Alaric - comes to say goodbye to Jeremy, and the look on Jeremy's face as he realizes that Elena is dead as well
  • Basically most of The Departed is a magical tear-generating machine. The flashbacks are upsetting since we know where they're going; the various tearful goodbyes, the melancholy musings...
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