Episode 1
Aired Oct 8, 2015
Day One of Twenty-Two Thousand, Give or Take
Damon 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.
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Episode 2
Aired Oct 15, 2015
Never Let Me Go
Damon 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.
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Episode 3
Aired Oct 22, 2015
Age of Innocence
Damon, 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.
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Episode 4
Aired Oct 29, 2015
I Carry Your Heart With Me
An 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.
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Episode 5
Aired Nov 5, 2015
Live Through This
Damon 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.
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Episode 6
Aired Nov 12, 2015
Best Served Cold
Lily 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.
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Episode 7
Aired Nov 19, 2015
Mommie Dearest
Damon 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.
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Episode 8
Aired Dec 3, 2015
Hold Me, Thrill Me, Kiss Me, Kill Me
While 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.
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Episode 9
Aired Dec 10, 2015
Cold as Ice
As 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.
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Episode 10
Aired Jan 29, 2016
Hell Is Other People
When 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.
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Episode 11
Aired Feb 5, 2016
Things We Lost in the Fire
While 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.
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Episode 12
Aired Feb 12, 2016
Postcards From the Edge
When 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.
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Episode 13
Aired Feb 19, 2016
This Woman's Work
Pregnancy 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.
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Episode 14
Aired Feb 26, 2016
Moonlight on the Bayou
Stefan 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.
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Episode 15
Aired Mar 4, 2016
I Would for You
Stefan 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.
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Episode 16
Aired Apr 1, 2016
Days of Future Past
Damon offers to have Stefan's scar transferred to his own body; Rayna gets closer to Stefan; Valerie tries to reason with Damon.
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Episode 17
Aired Apr 8, 2016
I Went to the Woods
After 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.
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Episode 18
Aired Apr 15, 2016
One Way or Another
Damon 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.
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Episode 19
Aired Apr 22, 2016
Somebody That I Used to Know
Rayna 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.
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Episode 20
Aired Apr 29, 2016
Kill 'em All
Damon 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.
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Episode 21
Aired May 6, 2016
Requiem for a Dream
Damon'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.
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Episode 22
Aired May 13, 2016
Gods & Monsters
Damon, 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.
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