Emily Chang

In the season premiere, after spending four months coping with the loss of Damon in a potentially dangerous way, Elena returns to Whitmore College for her sophomore year.

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 (recurring guest star Gabrielle Walsh – Paranormal Activity: The Marked Ones), a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp (recurring guest star Colin Ferguson – Eureka), 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.

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 (recurring guest star Jodi Lyn) 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 (recurring guest star Colin Ferguson) 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.

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 (recurring guest star Marco James – The Client List). Tyler, still working on controlling his anger issues, asks Liv (recurring guest star Penelope Mitchell – Hemlock Grove) 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.

With Homecoming around the corner, Elena invites Liam (recurring guest star Marco James) 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 (recurring guest star Jodi Lyn O-Keefe) 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.