S4, E17: Realizing that Elena needs some time away from Mystic Falls, Damon takes her to New York City, where he lived and partied hard in the 1970s. When Rebekah (recurring guest star Claire Holt) also shows up in New York, she’s impressed with Elena’s secret agenda. Flashbacks reveal Damon’s hedonistic life in the underground club scene and a complicated encounter with Lexi (recurring guest star Arielle Kebbel). Meanwhile, Caroline and Stefan try to convince Klaus that it would be in his own best interest to help them track Silas down, and Bonnie struggles to keep her grasp on reality and do the right thing. The band Dead Sara performs.