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.
When the past comes back to haunt her, Elena is forced to face her problems head on. After a night out at the annual Whitmore Medical Center Fundraiser, Jo (recurring guest star Jodi Lyn O’Keefe) opens up to Alaric about her own tragic past. Meanwhile, Stefan, Matt and Enzo resort to extreme measures when Tripp (recurring guest star Colin Ferguson) withholds information about his vampire-killing operation, and when Sheriff Forbes (recurring guest star Marguerite MacIntyre) gets caught in the middle of a dangerous plan, Caroline is in a race against the clock. Elsewhere, Tyler and Liv (recurring guest star Penelope Mitchell) grow closer, and Damon stumbles upon a startling clue that renews his hope.
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.
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 O’Keefe) 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.
When Alaric realizes that Jo (recurring guest star Jodi Lyn O’Keefe) can’t be compelled, he asks Elena to do some digging into her background. After learning that Enzo has been captured by Tripp (recurring guest star Colin Ferguson), Caroline teams up with Matt and Stefan to rescue him before Tripp learns their true identities. Armed with some new information about her past, Sarah (recurring guest star Gabrielle Walsh) breaks into Tripp’s office and is surprised when she finds Matt there, doing some investigating of his own. Meanwhile, Elena is forced to deal with the consequences of her actions, and Jeremy hits rock bottom, lashing out in a destructive way. Lastly, Damon is determined to take matters into his own hands when he receives some upsetting news.
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