On the morning of Elena's 18th birthday, Caroline is busy planning a party, but Elena is focused on searching for any clues that might help her discover where Stefan is. Damon is also searching for Stefan, while trying to protect Elena and keep her from doing anything that would draw Klaus' attention. Meanwhile, Klaus and Stefan are busy trailing a werewolf named Ray Sutton. Now working at the Mystic Grill along with Matt, Jeremy is struggling to understand why he keeps seeing the ghosts of Vicki and Anna since he was brought back to life by Bonnie's magic. Meanwhile, Alaric does his best to watch over Elena and Jeremy, while dealing with his grief over Jenna's death. Finally, Caroline and Tyler face a new and unexpected challenge.

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.