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Damon approaches Jeremy, who goes into an isolated storage room. Deducing that Kol ordered him to kill Jeremy, Damon warns Elena to keep him away from her brother. He follows Jeremy down a passageway under the bar, warning Jeremy that he has been sent to kill him. In Shane's study, Rebekah tortures the man (who kills himself by biting off his ...
Damon admits that he loves her and Elena kisses him when Katherine arrives with Klaus’ blood. Damon drinks it and gets healed while Katherine informs them that Stefan sacrificed everything to save his brother and he will leave town with Klaus. The episode ends with Jeremy seeing Vicki (Kayla Ewell) and Anna's ghosts.
After Katherine kills Jeremy in 'Down the Rabbit Hole' Damon stays behind determined to find the missing Bonnie, telling Stefan he cannot come home without her. Eventually he finds Bonnie, hugging her in relief, but when the two arrive back in Mystic Falls in informs Stefan Bonnie has lost her mind.
Back at the college, Bonnie tells Jeremy (Steven R. McQueen) about the Ball when Damon appears to ask for Bonnie's help about a locator spell. Bonnie reminds him that she is not a witch anymore. Damon and Enzo kidnap Jeremy and threatened to kill him to make her find them a witch who can make the spell.
Klaus blames Damon for all of the failed attempts at making Jeremy complete the hunters mark. Damon informs Klaus that he could have Jeremy wanting to kill Elena every time he saw her. Klaus taunts Damon saying that there has to be an explanation for Elena overlooking all of the horrible things that Damon has done to her and the people she loves.
However, Jeremy witnesses Stefan kill Vicki (after Damon turned her into a vampire). At Elena's request, Damon makes Jeremy forget this, and Jeremy becomes more stable and stops using drugs. Jeremy then starts a relationship with a vampire named Anna, but John Gilbert, Jeremy's uncle, kills Anna at the end of season one.
He shows Damon a stake and says he came there to kill him, but then throws it away. Damon asks him why he changed his mind. Jeremy says his father and his uncle hated vampires because they were taught to, but he realizes that killing Damon wouldn’t solve anything. Damon says his father felt the same way. Jeremy leaves.
Jeremy witnesses this and Elena asks Damon to make Jeremy forget this to spare him the pain. Matt on the other hand is devastated. After the history teacher is killed, a man named Alaric is hired to take his place. Alaric came to town to kill Damon, believing him to have killed his wife, Isobel.