With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon's mother Lily, who is trapped in the 1903 prison world. Meanwhile, when Caroline's plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric's 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.
Elenco: Paul Wesley , Ian Somerhalder , Kat Graham , Candice King , Zach Roerig , Matthew Davis , Michael Malarkey , Michael Trevino , Susan Walters , Zach Roerig , Bianca Lawson , Candice Accola , Claire Holt , Daniel Gillies , Katerina Graham , Matthew Davis , Rebekah , Sara Canning , Steven R. McQueen , Torrey DeVitto .