Just as Damon (Ian Somerhalder) thinks he's gained the upper hand in his fight against Lily (guest star Annie Wersching), an unexpected turn of events leaves him scrambling for a plan B. Elsewhere, when the fallout of Damon’s actions gains the unwanted attention of Mary Louise (guest star Teressa Liane) and Nora (guest star Scarlett Byrne), Stefan (Paul Wesley) and Caroline (Candice King) are forced to spend the night distracting the girls at Whitmore College's Heaven & Hell ball. Finally, after suspecting that she's up to something, Enzo (Michael Malarkey) sets off on a mission to find out what Valerie (guest star Elizabeth Blackmore) is hiding, while a plan set by Alaric (Matt Davis) and Bonnie (Kat Graham) leaves their worlds turned upside down.
