Patrick and the team travel to Hollywood to investigate the murder of a movie producer.
In the aftermath of a clever plan orchestrated by Lily (recurring guest star ANNIE WERSCHING), 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.
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.
With the traumatic effects of the Phoenix stone taking a toll on his brother, Stefan attempts to help Damon regain his grip on reality, while secretly struggling with his own experience in the stone. Elsewhere, Matt and Bonnie deal with the fallout after Julian (recurring guest star TODD LASANCE) and his men take over Mystic Falls, leading Matt to spiral out of control and into trouble with an officer named Penny (recurring guest star ANA NOGUEIRA). Meanwhile, Tyler (guest star MICHAEL TREVINO) returns to town for Alaric's baby shower and Caroline makes an upsetting discovery involving Alaric and his future plan for the babies.
As Enzo (Michael Malarkey) continues to fight the control over him, Bonnie (Kat Graham) finds herself at the center of a deadly game and forced to make a heart wrenching decision involving two of the most important people in her life. At the Armory, Alaric (Matt Davis) researches a mysterious artifact that he hopes will help in their fight to get Damon (Ian Somerhalder) and Enzo back. Finally, Damon’s downward spiral leads him to Tyler Lockwood (guest star Michael Trevino) who attempts to talk some sense into him before it’s too late. Paul Wesley and Candice King also star.
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