WELCOME TO THE BITTER BALL — 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 (guest star Penelope Mitchell), who appears to be dabbling in witchcraft. Tyler starts to worry about Matt’s relationship with Nadia (guest star Olga Fonda). After making a disturbing discovery, Stefan has a frustrating conversation with Damo and Enzo (guest star Michael Malarkey). Dr. Wes (guest star Rick Cosnett) struggles to continue his research project with help from a new benefactor named Sloan (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. Darren Genet directed the episode written by Rebecca Sonnenshine & Holly Brix.