When Elena and Katherine have the same dream that Stefan is in danger and desperately needs their help, they convince Damon to help them find Stefan. However, their plans are thwarted by a mysterious young woman named Tessa who seems to know everything about Stefan's history. In flashbacks to a distant time and place, Tessa reveals the shocking secrets in her past and what she has planned for the future. She also has a disturbing message for Damon about his own future. Silas forces an unwilling accomplice to help him search for Katherine, leading to a confusing and life-threatening situation for Matt. Finally, Silas reveals the reason he's determined to find Katherine, and Damon and Elena face a disturbing new reality.

On campus, Elena is touched by a sad and secretive student named Aaron. Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. At the ball, Elena shares a dance with Dr. Maxfield, who has a disturbing message for her. Caroline's evening at the ball takes her from happiness to heartbreak. Meanwhile, Nadia reveals her surprising history to Katherine, and Damon tries to make a deal with Silas. But when Silas demands that Damon commit an unthinkable act, it leads to a violent confrontation.

Back to Katherine's early life 1490, Nadia helps her mom with a fighting plan.

As Damon's behavior escalates from destructive to deadly, Stefan begins to regret their last conversation and decides to track Damon down and intervene. For reasons of her own, "Elena" volunteers to come along. Dr. Wes enlists the Travelers to set a trap that will once again test Damon's friendship with Enzo. After a heart-to-heart talk with Nadia, Matt enlists Caroline and Tyler's help to protect Elena, leading to a violent confrontation. Later, when Stefan tries to comfort a dejected Caroline, their conversation leads to a horrifying realization.