While You Were Sleeping – 5x16
Original air date: March 21, 2014
When Stefan tries to explain recent events to a very sick Elena, her first instinct is to call Damon. At the same time, Damon is trying to figure out how to make a disturbing confession to Elena. While going through Dr. Wes’ files, Caroline discovers a frightening secret, and is surprised when Enzo appears, claiming to have the solution everyone is searching for. At Enzo’s insistence, Caroline asks Stefan to meet her at a mysterious location where they are joined by a group of Travelers, including Sloan, who reveals new information on the importance of doppelgangers. During spring break on a mostly deserted Whitmore campus, Elena runs into Luke, a student who seems to know her, though she has no memory of meeting him. Recently dumped by his boyfriend, Luke proposes that he and Elena spend the break getting drunk together, but she sends him off on an urgent mission to find Bonnie and the “newbie” witch, Liv. Damon finally tells Elena the truth about his recent activities, and they come to a new agreement about their relationship.