Elena asks Stefan to escort her to the town's annual Founder's Party. Vicki gets Tyler to ask her to the party, then accuses him of trying to hide their relationship from his family. Zach reveals a useful family secret to Stefan. At the party, Damon tells Elena a story about the Salvatore family's past, leaving Elena with questions that Stefan refuses to answer. Finally, Stefan takes action to get Damon out of his life for good.

As Vicki’s behavior becomes more dangerous, Stefan tries to help her. Elena tries to convince Jeremy to stay away from Vicki. Caroline gives Bonnie a necklace she took from Damon to wear with her Halloween costume, and when Damon tries to take it back, he is surprised by Bonnie’s abilities. Bonnie discusses the incident with Grams and learns more about her family’s past. Trying to cheer Vicki up, Matt takes her to the high school’s haunted house, but the evening soon takes a terrifying turn.

The second season begins with Elena discovering her uncle John's bloody body and learning Jeremy's fate, and Damon realizing that Katherine has returned. Meanwhile, Caroline is taken to the hospital following a car accident, and Tyler's mysterious uncle Mason arrives in town.

Klaus puts a plan in motion that will give him even more power, but even with the unwilling participation of werewolf Ray Sutton, things don’t go exactly as Klaus had planned. Damon and Alaric reluctantly go along with Elena’s new strategy to find Stefan, leading Damon into a dangerous fight with an unexpected enemy. Jeremy turns to Matt for help as he continues to try to understand what the ghosts from his past want from him. Unaware that Caroline is in need of his help, Tyler faces an emotional confrontation with his mother.