COSTUME PARTY OF THE DAMNED – On campus, Elena (Nina Dobrev) is touched by a sad and secretive student named Aaron (guest star Shaun Sipos). Elena and Damon (Ian Somerhalder) attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. At the Ball, Elena shares a dance with Dr. Maxfield (guest star Rick Cosnett), who has a disturbing message for her. Caroline’s (Candice Accola) evening at the Ball takes her from happiness to heartbreak. Meanwhile, Nadia (guest star Olga Fonda) reveals her surprising history to Katherine (Nina Dobrev), and Damon tries to make a deal with Silas (Paul Wesley). Silas’ demand that Damon commit an unthinkable act leads to a violent confrontation. Kat Graham and Zach Roerig also star. Kellie Cyrus directed the episode written by Sonny Postiglione (#505).