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. Silas’ demand that Damon commit an unthinkable act leads to a violent confrontation.
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