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).

Damon and Elena are skeptical of Silas's new goal; Tessa realizes she was outsmarted by Silas; after discovering a new consequence of becoming human, Katherine decides she needs a new place to stay; Bonnie is impressed with Jeremy.

Hoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student named Liv, who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia. After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo. Dr. Wes struggles to continue his research project with help from a new benefactor named Sloan. Still bent on revenge, Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them, but their plan takes an unexpected and horrifying turn.