At a fraternity costume party, Damon gives Elena a lesson in choosing a victim. Klaus reveals an encounter with a group of vampire hunters - flashing back to 12th century Italy.

Stefan and Klaus form an uneasy alliance to try and contain the danger that Connor (TODD WILLIAMS) has unleashed. Professor Shane (DAVID ALPAY) works with Bonnie.

Terrifying hallucinations leave Elena shaken and confused and she makes a painful confession to Stefan. Matt gives Damon startling information about Professor Shane (DAVID ALPAY).

At the annual Miss Mystic Falls Pageant, Elena and Caroline give April (GRACE PHIPPS) advice, while Tyler and Hayley (PHOEBE TONKIN) work together on a secret project.

Damon and Stefan visit New Orleans in hopes of finding someone who remembers their last visit in 1942. MADELINE ZIMA (Californication) guest stars as one of Damon's former flames.

It's a winter wonderland in Mystic Falls. Plus, Professor Shane (DAVID ALPAY) reveals a piece of ancient history that leaves everyone speechless.

Rebekah (CLAIRE HOLT) is back with a vengeance. Bonnie is uncomfortable when her father, Rudy Hopkins (RICK WORTHY - Supernatural), accepts the role of Interim Mayor.

Jeremy is furious when Klaus tries to control him by putting Matt's life in danger. Damon coaches Jeremy as he prepares to take on Klaus' new vampires, but they find that Kol has beaten them to it. Kol makes it clear that he will stop at nothing to convince everyone to give up the search for the cure. Looking for a new ally, Rebekah reminds Stefan that they were once close friends. When Sheriff Forbes and Mayor Hopkins question Shane about his involvement in the Founders' Council deaths, Bonnie steps in with questions of her own, and Shane's responses push Bonnie to the edge of her powers. Elena negotiates with Klaus to keep Jeremy safe, but when danger suddenly appears from a totally unexpected enemy, Elena comes up with her own daring plan for Jeremy.

Shane (DAVID ALPAY) leads an expedition to a desolate island, where he believes the secret of the cure lies hidden. Rebekah (CLAIRE HOLT) and Elena continue their bitter rivalry.

Damon has an ugly run-in with a Hunter, Vaughn (CHARLIE BEWLEY - The Twilight Saga), and realizes he is one of the Five. Stefan admits his feelings about possibly becoming human.

Damon and Rebekah (CLAIRE HOLT) learn an unexpected bit of recent history from Vaughn (CHARLIE BEWLEY). Bonnie reveals the rest of Shane's (DAVID ALPAY) plan.

Realizing that Elena needs some time away from Mystic Falls, Damon takes her to New York City. Flashbacks reveal Damon's hedonistic life there in the 1970s.