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Just as Damon thinks hes 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 Damons actions gains the unwanted attention of Mary Louise and Nora, Stefan and Caroline are forced to spend the night distracting the girls at Whitmore Colleges Heaven & Hell ball. Finally, after suspecting that shes 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.