Realizing that Elena (Nina Dobrev) needs some time away from Mystic Falls, Damon (Ian Somerhalder) takes her to New York City, where he lived and partied hard in the 1970s. When Rebekah (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 (guest star Arielle Kebbel). Meanwhile, Caroline (Candice Accola) and Stefan (Paul Wesley) try to convince Klaus (Joseph Morgan) that it would be in his own best interest to help them track Silas down, and Bonnie (Kat Graham) struggles to keep her grasp on reality and do the right thing.