Sherod Ogletree

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.

At Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse suddenly needs Caroline's help. At Elena's request, Damon comes up with an effective method to get Wes to answer his questions. At the party, Elena finds that she and Aaron have a lot in common, and Caroline grows more concerned about Jesse. Meanwhile, Katherine does a favor for Matt and manages to get through to Stefan, who is still struggling to overcome the events of the summer. Finally, Bonnie does her best to cope with her new reality, and Damon makes a terrifying discovery about a secret society.