S5, E13: 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 (recurring guest star Penelope Mitchell – Hemlock Grove), who appears to be dabbling in witchcraft. Tyler starts to worry about Matt’s relationship with Nadia (recurring guest star Olga Fonda). After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo (recurring guest star Michael Malarkey). Dr. Wes (recurring guest star Rick Cosnett) struggles to continue his research project with help from a new benefactor named Sloan (recurring guest star Caitlin McHugh). 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.