Hoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student named Liv, who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia. After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo. Dr. Wes struggles to continue his research project with help from a new benefactor named Sloan. Still bent on revenge, Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them, but their plan takes an unexpected and horrifying turn.

While Nadia remembers her centuries-long search for her mother, Stefan, Caroline and Matt come up with a desperate new plan to save Elena's life. For the second time, Bonnie and Jeremy must turn to Liv for help. Damon baits Tyler into a nasty confrontation, then takes off to seek revenge on Dr. Wes. Caroline and Tyler come to a new understanding. Finally, Bonnie learns of a terrifying secret that will threaten the lives of all her friends.

Damon tries to figure out how to make a disturbing confession to Elena.

Bonnie has an unsettling encounter with Luke (CHRIS BROCHU), and learns more about his family history. The Travelers' leader, Markos (RAFFI BARSOUMIAN), arrives in Mystic Falls.

Elena and Stefan start having dreams about an alternate version of their lives; The Travelers move in on Mystic Falls; Matt has a frightening encounter on the Other Side.

Enzo holds Elena, Stefan and Bonnie hostage to uncover the truth about the love of his life. Markos performs a ritual to undo witch's magic.

When Stefan and Elena escape from Markos' control, only to find themselves Stranded in a remote location, Stefan gets philosophical with Elena about her relationship with Damon. After their attempt to protect the doppelgangers goes badly, Liv and Luke come up with a dangerous new strategy. Damon recruits Matt and Jeremy to help him set a trap for Markos, who turns out to have a devastating surprise of his own. Bonnie finally admits to Caroline that she's been keeping the truth about the Other Side from everyone. Finally, while Bonnie searches desperately for a way to stop Markos, Caroline is witness to an unthinkable act of violence by one of the Travelers.

Damon's plan causes a huge explosion in Mystic Falls, and everyone is caught up in the confusion, leaving a trail of heroism, sacrifice, relief and despair.

Four months have gone by since the Other Side broke down and Bonnie and Damon were lost. Mystic Falls is still a supernatural-free area. Everyone is grieving in their own ways, and some worse than others.

Caroline admits that she has feelings for Stefan. Bonnie and Damon find clues that make them think they might not be alone.

Elena invites Liam to a party at the corn maze; Stefan shows up asking Caroline for help with a mess created by Enzo; Tyler winds up in a dangerous position.

Elena is forced to confront her problems; Liv and Tyler get closer; Damon finds a surprising clue that renews his hope.

Elena gets some hopeful news from Alaric and Stefan regarding the Gemini Coven; Tyler tries to help Liv and Luke after learning of disturbing plans the coven has for them; dinner takes a drastic turn for Jo; Kai makes a dangerous discovery.

Elena and Damon enter the prison world to bring Bonnie home. Complications arise when Kai escapes and finds Liv. Stefan finds out the truth about Sarah.

Bonnie tries to replicate her favorite traditions, while reminiscing about happier times with her friends; Sheriff Forbes brings holiday cheer to Caroline at Whitmore College; Alaric turns to Damon and Elena for help when Jo goes missing; Tyler approaches Liv and Luke with a risky plan; Jeremy helps Matt carry out a plan to take down Enzo; Stefan is forced to break some devastating news to Caroline.

As Kai learns how to control his magic, he holds Elena captive; Caroline and Stefan go to North Carolina in search of a cure for Sheriff Forbes; Damon realizes Elena has been kidnapped.

Caroline struggles to save her mother. Damon comes up with a daring new plan. Jo and Kai prepare to merge, but Luke intervenes.

Elena is determined to celebrate Bonnie's birthday; after learning Stefan's secret, Enzo wants to interfere in Sarah Salvatore's life; Caroline struggles to cope with everything going on around her.

Elena and Bonnie help Jo with last minute wedding preparations.

In the aftermath of Jo and Alaric's wedding, an unexpected, and definitely uninvited guest shows up, putting Elena's life in jeopardy. Despite Matt's attempt to leave town to save himself, Bonnie takes matters into her own hands after finding herself on the receiving end of a twisted plan.