Just as Damon thinks he's gained the upper hand in his fight against Lily (recurring 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 (recurring guest star Teressa Liane) and Nora (recurring guest star Scarlett Byrne), Stefan and Caroline 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 sets off on a mission to find out what Valerie (recurring guest star Elizabeth Blackmore) is hiding, while a plan set by Alaric and Bonnie leaves their worlds turned upside down.