The Downward Spiral, 03/12
IAN SOMERHALDER MAKES HIS DIRECTORIAL DEBUT �" After shutting off her humanity following the death of her mother, Caroline (Candice Accola) gives her friends an unexpected ultimatum. Not knowing how to handle the new Caroline, Stefan’s (Paul Wesley) attempt to intervene sets off a dangerous chain of events, leaving him and Elena (Nina Dobrev) in a race against the clock. Meanwhile, after seeking answers from Kai (guest star Chris Wood) about the prison world, Damon’s (Ian Somerhalder) world is turned upside when he learns some devastating news about his mother Lily (guest star Annie Wersching). Elsewhere, Enzo (Michael Malarkey) finds himself becoming increasingly intrigued by Sarah Salvatore (guest star Tristan Mays), and Bonnie (Kat Graham) begins to struggle with the effects of being back in the real world. (#616).
A Bird in a Gilded Cage, 03/19
DAMON TRAVELS TO THE 1903 PRISON WORLD -- With the help of Bonnie (Kat Graham) and Kai (guest star Chris Wood), Damon (Ian Somerhalder) and Elena (Nina Dobrev) set forth a plan to rescue Damon’s mother Lily (guest star Annie Wersching), who is trapped in the 1903 prison world. Meanwhile, when Caroline's (Candice Accola) plan for Stefan (Paul Wesley) backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo (Michael Malarkey) and Alaric’s (Matt Davis) attempt to reel Caroline back in doesn’t quite go as planned when they realize they're outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core. Joshua Butler directed the episode written by Neil Reynolds (#617).