A fellow Whitmore student named Jesse gives Elena some intriguing information about Professor Wes Maxfield. Damon asks for help finding Stefan.

Damon and Elena try to help Stefan through a confusing time, which ends up taking Elena on an emotional journey. Caroline makes an effort to know Jesse better.

Elena meets a sad and secretive student on campus. Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. While there, Elena receives a disturbing message from Dr. Maxfield. Nadia reveals her surprising history to Katherine;. Silas demands that Damon commit an unthinkable act.

Silas announces his new goal to Damon and Elena. Tessa tells Stefan about her next move. Katherine discovers an unexpected consequence of being human and realises she needs a new place to stay. Bonnie is touched by Jeremy's determination to stand by her. Damon is stunned when he learns the secret to Tessa's plan.

Dr. Wes gives Katherine some disturbing news. Jeremy and Bonnie share a glimmer of hope after talking with Amara. Silas fails to keep a promise which causes Damon to turn to Tessa for help with his new plan. Stefan makes a heartbreaking confession to Damon and Elena.

Elena and Caroline plan a big party at school, but their plans are interrupted when Jesse suddenly needs Caroline's help. Meanwhile, Damon makes a terrifying discovery about a secret society.

Caroline offers Stefan an unusual form of therapy. Meanwhile, Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades, and she shares with him some disturbing information she recently learned about her family.

Damon is forced to deal with a part of his past he thought was gone forever when Dr. Wes unleashes a secret weapon to stop him from rescuing Elena. Elena learns about the dark history of Whitmore College. Katherine turns to Matt for help.

Caroline convinces Elena and Bonnie to attend Whitmore College's Bitter Ball for broken-hearted students. Bonnie meets a fellow student who appears to be dabbling in witchcraft. Tyler worries about Matt's relationship with Nadia. Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them get revenge, but their plan takes a horrifying turn.

Damon's behavior escalates from destructive to deadly. Stefan begins to regret their last conversation and tries to track Damon down and intervene. Dr. Wes enlists the Travelers to set a trap that will test Damon's friendship with Enzo; and a talk between Caroline and Stefan leads to a horrifying realization.

Nadia recalls her centuries-long search for her mother. Stefan, Caroline and Matt come up with a desperate plan to save Elena's life. Damon baits Tyler into an ugly confrontation and seeks revenge against Dr. Wes. Bonnie learns a terrifying secret that threatens the lives of all her friends.