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** The background music, Music/ChristinaGrimmie's "With Love", especially if you know what happened to her.

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** The background music, BackgroundMusic, Music/ChristinaGrimmie's "With Love", especially if you know what happened to her.
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* "Katerina" shows the [[StartOfDarkness start of Katherine's descent into darkness]]. It was full of tearjerking moments, and portrayed Katherine surprisingly [[JerkassWoobie sympathetically]].

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* "Katerina" shows the [[StartOfDarkness start of Katherine's descent into darkness]]. It was full of tearjerking moments, and portrayed Katherine surprisingly [[JerkassWoobie sympathetically]]. Near the end of the episode she finds a centuries-old drawing of her family preserved in a book and tearfully touches the images of her parents' faces. Cue waterworks.
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** The background music, Music/ChristinaGrimmie's "With Love", especially if you know what happened to her.
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* At the end of season 3/beginning of season 4, [[spoiler: Elena becomes a vampire. All that struggling to hold on to her humanity, in stark contrast to [[{{Twilight}} a certain other vampire-dating girl]] ]], we might add, and it's all for nothing.

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* At the end of season 3/beginning of season 4, [[spoiler: Elena becomes a vampire. All that struggling to hold on to her humanity, in stark contrast to [[{{Twilight}} [[Literature/{{Twilight}} a certain other vampire-dating girl]] ]], we might add, and it's all for nothing.
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Linking directly instead of through redirect.


*** And after [[spoiler: their BigDamnKiss]] DAMN!!!!

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*** And after [[spoiler: their BigDamnKiss]] [[spoiler:TheBigDamnKiss]] DAMN!!!!
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* Rebekah confessing that she wants the cure so that she can have a normal life: to live, and dance, have children and grow old with someone who loves her. What makes this scene even worse is that she's confessing this to Stefan, who'd spent the entire evening with her at the cancelled school dance, just so he can get her dagger to put Kol down. And she just gives him the dagger, fully expecting him to use it on her, just like everyone else has done in her life. That's how badly she's been let down/betrayed/manipulated by people throughout her vampiric existence. [[spoiler: Which makes Stefan's decision ''not'' to use it a CrowningMomentofHeartwarming]]

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* Rebekah confessing that she wants the cure so that she can have a normal life: to live, and dance, have children and grow old with someone who loves her. What makes this scene even worse is that she's confessing this to Stefan, who'd spent the entire evening with her at the cancelled school dance, just so he can get her dagger to put Kol down. And she just gives him the dagger, fully expecting him to use it on her, just like everyone else has done in her life. That's how badly she's been let down/betrayed/manipulated by people throughout her vampiric existence. [[spoiler: Which makes Stefan's decision ''not'' to use it a CrowningMomentofHeartwarming]]SugarWiki/{{Heartwarming Moment|s}}]]



* It overlaps with CrowningMomentofHeartwarming, but seeing [[spoiler: Elena's grief-stricken, shocked reaction when Damon snaps Matt's neck...and then her joy when she finds out that he was wearing Jeremy's ring...and then watching her sob and cry as the guilt and weight of all her actions finally bears down on her.]]

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* It overlaps with CrowningMomentofHeartwarming, SugarWiki/HeartwarmingMoments, but seeing [[spoiler: Elena's grief-stricken, shocked reaction when Damon snaps Matt's neck...and then her joy when she finds out that he was wearing Jeremy's ring...and then watching her sob and cry as the guilt and weight of all her actions finally bears down on her.]]
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* In the finale, [[spoiler: Anna's death.]]

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* In the Season 1 finale, [[spoiler: Anna's death.]]
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plot point described turned out not to be true in later episodes


** Even worse, [[spoiler: because of her doppleganger nature, Elena can't feed on animals or from blood bags. Meaning Elena has no choice but to bite people, running the very real risk of killing someone.]]
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* The fact that [[spoiler: every supernatural character who died on the show and never made it back from the Other Side is gone for good, which - unless there's a way out - means that Vicki, Grams and Lexi are never coming back.]]

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* The fact that [[spoiler: every supernatural character who died on the show and never made it back from the Other Side is gone for good, which - unless there's a way out - means that Vicki, Grams and Lexi are never coming back.]]]]
*The death of Elizabeth Forbes. Caroline's reaction, Damon's reaction, her funeral. All of it.
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* Jonas's desperate attempt to bring his son back to life, only to find out that he can't.

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