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In Total Eclipse of the Heart, Whitmore College organizes a Bitter Ball for broken hearted students.
Damon and Enzo find Bonnie and Jeremy and interrupt them from going to the ball. They explain to Bonnie that they need to find Dr Wes so Bonnie will find someone to do the locator spell or Enzo is going to kill Jeremy. While Jeremy says that Damon is not going to hurt him, because Elena would never forgive him, Damon proves him wrong and says that Elena has already given up on him and takes Jeremy hostage while Bonnie is trying to figure out how to get some witch for locator spell to save Jeremy.
At the Bitter Ball, Katherine who is possessing Elena's body and Stefan share a dance and she tries to convince him that she has given up on Damon but they are interrupted by Caroline which makes Katherine wonder if Caroline has feelings for Stefan. Later, Damon and Bonnie arrive and meet Stefan and Caroline and Bonnie explains the situation to them. They show a photo of Jeremy being kidnapped by Enzo and Katherine appears and pretends to be panicked. She later begs Stefan to help her find Jeremy. Bonnie finds Liv asking for her help and she is able to locate Wes.
- Katherine in Elena's body shares a dance with Stefan.
- Caroline destroys a drawing made by Klaus for her because she wants to move on from the relationship.