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.

A fellow Whitmore student named Jesse gives Elena some intriguing information about Professor Wes Maxfield. Damon asks for help finding Stefan.

Damon and Elena try to help Stefan through a confusing time, which ends up taking Elena on an emotional journey. Caroline makes an effort to know Jesse better.

Elena meets a sad and secretive student on campus. Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. While there, Elena receives a disturbing message from Dr. Maxfield. Nadia reveals her surprising history to Katherine;. Silas demands that Damon commit an unthinkable act.

Elena and Caroline plan a big party at school, but their plans are interrupted when Jesse suddenly needs Caroline's help. Meanwhile, Damon makes a terrifying discovery about a secret society.