Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire who hasn't really moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus' whereabouts from an unexpected source, he and Elena follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help.
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.