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In the aftermath of a clever plan orchestrated by Lily (recurring guest star Annie Wersshing), Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother. Meanwhile, Caroline, who is being held hostage by the Heretics, learns some shocking information about Valerie's (recurring guest star Elizabeth Blackmore) past, while Stefan learns a few unexpected details about his own past from Lily. Finally, Alaric turns to Bonnie for her help after coming clean about a secret he's been keeping.