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.

Elena comes to terms with the loss of Damon with the help of Alaric. Enzo convinces Caroline to join him as he tracks down Damon and Bonnie. Meanwhile, Matt worries about Jeremy who is spending time with Sarah, a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp, leader of the community protection program, tells Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly band together to uncover the mystery of where they are and how they are going to get back home.

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

Damon and Bonnie are trying to come up with a way to come back from the otherside, while Stefan tries to help Elena start fresh.

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 can't decide whether she wants her memories of Damon back; Alaric asks Elena to look into Jo's background; Tripp puts Damon, Enzo, and Alaric in mortal danger.

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 Jeremy reminisce about their past; Caroline and Stefan grow closer; Sheriff Forbes asks Damon for help with a case involving Elena's parents; Enzo lures Matt and Sarah into his plan.

Everybody gathers for the funeral of Liz Forbes. Elena is worried Caroline isn't coping as well as everyone believes.

Stefan blames himself for Caroline turning off her humanity. Bonnie is angry with Damon for aligning himself with Kai. Sarah's life is in danger.

Elena and Damon enter the 1903 prison world to bring back his mother. Stefan intends to exact revenge on Caroline. Bonnie cannot forgive Kai.

Damon concocts a risky plan involving Lily to stop Caroline and Stefan from wreaking havoc; Elena re-evaluates her life as a vampire after learning that Jo is pregnant; Sarah turns the tables on Enzo; Tyler and Matt wind up in danger.

Stefan concocts a plan to get Caroline to turn her humanity back on. Damon wrestles with what he should do with the cure. Enzo seeks answers.

Damon and Elena discuss the ramifications of Damon's offer. Alaric and Jo reluctantly participate in their bachelor and bachelorette parties. Lily continues on a dangerous downward spiral.

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.