As the fifth season opens, Elena, after a passionate summer with Damon, heads to college nearby with Caroline as her roommate. Plus, a terrifying appearance by Silas (Paul Wesley).
Without telling Elena that Stefan is missing, Damon turns to Sheriff Forbes (recurring guest star Marguerite MacIntyre) for help finding his brother. Elena and Caroline try to find out who is covering up a campus murder, and a fellow Whitmore student named Jesse (recurring guest star Kendrick Sampson – Greek) gives Elena some intriguing information about Professor Wes Maxfield (recurring guest star Rick Cosnett – The New Inventors). While Jeremy struggles to return to his old life, he continues to be the only person who can see and talk to Bonnie, but he can’t convince her that the time has come to let the others know she sacrificed her own life for his. After learning that Silas is searching for Katherine, Damon asks Matt and Jeremy to keep her out of sight, but the situation quickly spirals out of control. Finally, Nadia (recurring guest star Olga Fonda) uses violence to make a point about her own agenda.
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 (recurring guest star Janina Gavankar – True Blood) 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 (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.
The power of doppelgangers…. While Elena and Damon try to explain Amara’s (played by series star Nina Dobrev) situation to Stefan, Dr. Wes Maxfield (recurring guest star Rick Cosnett) gives Katherine some deeply disturbing news. Nadia (recurring guest star Olga Fonda) shows up at Caroline’s dorm room searching for Katherine. After a surprising conversation with Amara, Jeremy and Bonnie share a glimmer of hope. Silas fails to keep a promise, causing Damon to turn to Tessa (recurring guest star Janina Gavankar) for help with his new plan, and Stefan makes a heartbreaking confession to Damon and Elena.
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