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 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. 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.
Based on novels of the same name, Vampire Diaries follows Elena, a young heroine, who is the object of passion for two vampire brothers. Four months after the tragic car accident that killed their parents, 17-year-old Elena Gilbert and her 15-year-old brother, Jeremy are still trying to cope with their grief and move on with their lives. Elena has always been the star student; beautiful, popular and involved with school and friends, but now she finds herself struggling to hide her sadness from the world.
As the school year begins, Elena and her friends are fascinated by a handsome and mysterious new student, Stefan Salvatore. Stefan and Elena are immediately drawn to one another, and Elena has no way of knowing that Stefan is a centuries-old vampire, struggling to live peacefully among humans, while his brother Damon is the embodiment of vampire violence and brutality. Now these two vampire brothers - one good, one evil - are at war for Elena's soul and for the souls of her friends, family and all the residents of the small town of Mystic Falls, Virginia.