Just as Damon thinks he's gained the upper hand in his fight against Lily, 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 and Nora, 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 is hiding, while a plan set by Alaric and Bonnie leaves their worlds turned upside down.