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).

A fellow Whitmore student named Jesse (KENDRICK SAMPSON) gives Elena some intriguing information about Professor Wes Maxfield (RICK COSNETT). Damon asks for help finding Stefan.

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 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.