On campus, Elena is touched by a sad and secretive student named Aaron (recurring guest star SHAUN SIPOS – Melrose Place, Final Destination 2). 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 (recurring guest star RICK COSNETT), who has a disturbing message for her. Caroline’s evening at the ball takes her from happiness to heartbreak. Meanwhile, Nadia (recurring guest star OLGA FONDA) 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.