After spending the past four months coping with the loss of Damon in an unconventional and potentially dangerous way, Elena has returned to Whitmore College for the start of sophomore year. Unable to move on, Caroline is desperate to find a way to reverse the anti-magic spell the Travelers have put over Mystic Falls and grows frustrated when her calls to Stefan go unanswered. Tyler, who is human once again, has a run-in at a football tailgate that tests his ability to control his anger, while Matt worries that Jeremy is dealing with the loss of Bonnie in a self-destructive way. Alaric, who is struggling to adjust to his new life as a vampire, finds himself in an awkward situation when he meets Jo, a beautiful doctor at the university hospital. Last, while everyone believes Stefan is off tracking a lead to get Damon and Bonnie back, Elena is shocked when she learns the truth of what he has really been up to.

Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. 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, makes an interesting confession to 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.

In an attempt to bring some fun back into their lives, Elena persuades Caroline to meet her at the swimming hole where she plans to introduce her to Liam. Tyler, still working on controlling his anger issues, asks Liv for a favor and is surprised when she makes an unexpected confession. Stefan arrives back in Mystic Falls looking for Enzo and is caught off guard when he notices a strange change in Elena. Meanwhile, at the lake, Enzo’s actions cause Matt to make a startling revelation, and Jeremy makes a discovery about the anti-magic spell that could potentially put Elena’s life in danger. Elsewhere, Damon and Bonnie stumble upon clues that lead them to believe they’re not alone.

When Damon and Bonnie realize that uncovering a time in Damon’s past may provide clues to finding their way home, Damon is forced to relive one of the worst days of his life. After an awkward run-in with Jo at the hospital, Alaric steps in to help Jeremy get his life together and cope with the loss of Bonnie. Elsewhere, Stefan attempts to show Elena what it’s like to start over and create a new identity, while an unsuspecting Matt finds himself in a disturbing situation when Tripp lets him in on a dark secret. Lastly, Stefan, who is desperate to regain some normalcy in his life, is stunned when an unexpected visitor shows up.

With Homecoming around the corner, Elena invites Liam to attend a party at the corn maze with her. Instead of attending the homecoming festivities, Caroline is preoccupied after Stefan shows up unexpectedly and needs her help cleaning up a mess created by Enzo. Heeding Elena’s advice to be more social, Alaric reluctantly attends the party, but a devastating accident quickly leaves him and Jo rushing to save lives. Elsewhere, Tyler finds himself in a dangerous position when his werewolf curse is put to the test, and an emotionally embattled Stefan comes clean to Caroline about his intent to move on from Mystic Falls. Lastly, Damon and Bonnie make an important discovery that affects their quest to get back home.

Jo fortæller Alaric om sin egen tragiske fortid. Tyler og Liv får et tættere forhold, og Damon falder over et forbløffende spor, som giver ham fornyet håb.

Mens Elena og Caroline forbereder sig på at fejre ""Friendsgiving"" på deres kollegie, modtager de opløftende nyheder fra Alaric og Stefan.

Liv hjælper Damon og Elena med deres plan for at få Bonnie tilbage, men der sker noget uventet, og hun må træffe et vanskeligt valg. Enzo går over stregen.

Julen nærmer sig, og Bonnie forsøger at genskabe nogle af sine yndlingstraditioner, mens hun mindes gladere tider tilbage i Mystic Falls.

Kai holder Elena til fange, mens han lærer at kontrollere sine magiske evner. Caroline og Stefan leder efter en kur til sherif Forbes. Damon opdager, at Elena er blevet kidnappet.

Liv og Tyler forsøger at overtale deres far til at lade Jo og Kai tage deres pladser i ceremonien. Carolines plan om at helbrede hendes mor går ikke som ventet.

Elena er fast besluttet på at fejre Bonnies fødselsdag. Enzo ønsker at blande sig i Sarah Salvatores liv, efter at han hører om Stefans hemmelighed.

Elena og Jeremy mindes deres fortid. Caroline og Stefan får et tættere forhold, og sherif Forbes beder Damon om hjælp i forbindelse med en sag, der involverer Elenas forældre.

Alle samles til Liz Forbes' begravelse. Elena er bekymret for, at Caroline ikke klarer sig så godt, som alle tror. Famon giver Caroline gode råd.

Stefan bebrejder sig selv, at Care har slukket for sine følelser. Damon må fortælle sin bror, at deres mor er i live. Enzo begynder at få følelser for Sarah.

Damon rejser tilbage til et fængsel i 1903. Enzo og Alarics forsøg på at snørre Caroline går ikke som planlagt. En uventet gave fra Bonnie ryster Damon.

Stefan og Carolines menneskelighed er blevet slukket, og de begynder at skabe kaos på Whitmore. Damon finder på en risikabel plan, der involverer Lily.

Mens Damon spekulerer over, om han skal fortælle Elena om kuren, begynder han at snakke om deres fremtidige liv sammen, og om hvordan deres tilværelse ville være, hvis de ikke var vampyrer.

Alaric og Jo deltager modstræbende i deres respektive polterabender. Samtidig indser Enzo, at Lily befinder sig i en farlig nedadgående spiral.

Det er Alaric og Jos bryllupsdag, og Elena og Bonnie hjælper Jo med forberedelserne. Stefan opdager altafgørende nyheder, som Damon har skjult fra ham.

En uventet gæst dukker op, efter at Alaric og Jo er blevet gift, og det bringer Elena i stor fare. Damon skal træffe sit livs vanskeligste beslutning.