Episodes
Episode 1Aired Oct 8, 2015Day One of Twenty-Two Thousand, Give or TakeDamon is faced with a new reality without the love of his life; Bonnie decides to be Damon's moral compass, and looks out for Alaric, who lost his fiancee; Stefan protects the town from Lily; Enzo must decide who he is loyal to. DetailsEpisode 2Aired Oct 15, 2015Never Let Me GoDamon makes an impulsive decision that could undermine a deal between Lily and Stefan; Alaric asks Bonnie for help with a potentially dangerous artifact; Caroline uncovers a stunning secret. DetailsEpisode 3Aired Oct 22, 2015Age of InnocenceDamon, Bonnie and Alaric set off on a road trip in search of anything they can use against Lily; while held hostage by the Heretics, Caroline learns information about Valerie's past. DetailsEpisode 4Aired Oct 29, 2015I Carry Your Heart With MeAn unexpected turn of events sends Damon scrambling for an alternate plan; Damon's actions force Stefan and Caroline to distract girls at a ball at Whitmore College; Enzo is determined to find out what Valerie is hiding. DetailsEpisode 5Aired Nov 5, 2015Live Through ThisDamon decides to make a change; Lily gets ready for the arrival of someone special from her past; Bonnie and Enzo are faced with a violent threat; disturbing information regarding the phoenix stone emerges. DetailsEpisode 6Aired Nov 12, 2015Best Served ColdLily hosts a dinner to introduce her past love, Julian, to Damon and Stefan, and to declare peace between her family and the residents of Mystic Falls; Matt and Bonnie uncover a mystery; Alaric reaches his breaking point. DetailsEpisode 7Aired Nov 19, 2015Mommie DearestDamon and Stefan confront Lily with painful childhood memories; Lily reveals a secret; Enzo challenges Julian to a duel; Valerie reveals news that upturns Caroline's world. DetailsEpisode 8Aired Dec 3, 2015Hold Me, Thrill Me, Kiss Me, Kill MeWhile Julian and Lily host a party to celebrate Mary Louise and Nora's anniversary, Stefan and Damon initiate a risky plan; Caroline faces a new reality that threatens to destroy her relationship with Stefan; Lily makes a difficult decision. DetailsEpisode 9Aired Dec 10, 2015Cold as IceAs the holidays draw near, Stefan and Damon's search for Julian leads them to a town outside Mystic Falls; Bonnie becomes friendly with Nora during a toy drive; Alaric fears that Caroline is struggling with her pregnancy. DetailsEpisode 10Aired Jan 29, 2016Hell Is Other PeopleWhen Damon wakes in the Phoenix stone, he is faced with reliving a traumatic experience from the Civil War; Bonnie races to get Damon out of the stone before the experience forever changes him. DetailsEpisode 11Aired Feb 5, 2016Things We Lost in the FireWhile Stefan secretly struggles with his own experience in the Phoenix stone, he tries to help Damon recover and regain his grip on reality; Matt spirals out of control; Tyler attends Alaric's baby shower; Caroline makes an upsetting discovery. DetailsEpisode 12Aired Feb 12, 2016Postcards From the EdgeWhen Stefan tries to reason with an increasingly reckless Damon, he learns the devastating reason for his brother's behavior; Caroline turns to Valerie when she begins suffering dangerous side effects of her pregnancy. DetailsEpisode 13Aired Feb 19, 2016This Woman's WorkPregnancy complications threaten Caroline's life, prompting Stefan and Valerie to take extreme measures; Enzo uses Damon's secret as leverage to secure assistance in his search for Rayna Cruz, a ruthless vampire hunter. DetailsEpisode 14Aired Feb 26, 2016Moonlight on the BayouStefan goes to New Orleans to lure a vengeful vampire hunter away from his friends in Mystic Falls; Enzo comes to Damon and Bonnie with a plan; Caroline contemplates her future. DetailsEpisode 15Aired Mar 4, 2016I Would for YouStefan and Valerie pursue an herb that can hide them from Rayna; Bonnie makes a discovery that thwarts Damon's plan to take Rayna down; Stefan questions his future with Caroline; Matt decides it may be time to take a real stand against vampires. DetailsEpisode 16Aired Apr 1, 2016Days of Future PastDamon offers to have Stefan's scar transferred to his own body; Rayna gets closer to Stefan; Valerie tries to reason with Damon. DetailsEpisode 17Aired Apr 8, 2016I Went to the WoodsAfter his brother's decision, Stefan awakens to find himself in a life-or-death struggle; Damon follows a strange lead; Valerie goes to Dallas to get Alaric to help search for Stefan; Rayna discovers a new threat. DetailsEpisode 18Aired Apr 15, 2016One Way or AnotherDamon and an unwilling Alaric head to Memphis in hopes of capturing an escaped vampire and getting a lead on Stefan; Bonnie gets some information about why the Armory may be after her. DetailsEpisode 19Aired Apr 22, 2016Somebody That I Used to KnowRayna may be the key to Bonnie's survival after Enzo's efforts to protect her end up putting her life in danger; Stefan faces Alaric and tensions escalate. DetailsEpisode 20Aired Apr 29, 2016Kill 'em AllDamon and Enzo lead the charge to rescue Bonnie before her condition worsens; Stefan learns the source of Matt's anger toward him; Caroline realizes how much she misses her former supernatural lifestyle; Damon makes a fateful decision. DetailsEpisode 21Aired May 6, 2016Requiem for a DreamDamon's dangerous attempt to save Bonnie takes an unexpected turn, forcing everyone to come together to help her pull through; a new threat jeopardizes Caroline's life. DetailsEpisode 22Aired May 13, 2016Gods & MonstersDamon, Enzo and Caroline realize they must take drastic measures if they hope to save Bonnie; Stefan tells Caroline that they may need to bring Alaric and the twins into their plan; Damon must make a sacrifice. Details
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