With the traumatic effects of the Phoenix stone taking a toll on his brother, Stefan attempts to help Damon regain his grip on reality, while secretly struggling with his own experience in the stone. Elsewhere, Matt and Bonnie deal with the fallout after Julian and his men take over Mystic Falls, leading Matt to spiral out of control and into trouble with an officer named Penny.

Meanwhile, Tyler returns to town for Alaric's baby shower and Caroline makes an upsetting discovery involving Alaric and his future plan for the babies.

When his experience in the Phoenix stone leads him to do the unthinkable, Damon finds himself without a care in the world, spiraling out of control and under the influence of a dangerous and reckless Julian. Refusing to give up on his brother, Stefan attempts to reason with Damon only to uncover the devastating reason for his descent.

Elsewhere, Caroline begins having some dangerous side effects as a result of her supernatural pregnancy and is forced to turn to Valerie for help. Meanwhile, Bonnie, Nora and Mary Louise attempt to track down a ruthless vampire hunter named Rayna after they suspect that she has reemerged.

While Stefan and Valerie search for a magical herb that can keep him hidden from Rayna, Damon comes up with his own plan to take her down for good. However, while at The Armory, Bonnie makes a shocking discovery about Rayna that brings Damon’s plan to a screeching halt.

Elsewhere, a conversation with Caroline leaves Stefan questioning their future together, while Matt decides it may be time to truly take a stand against the vampires of Mystic Falls. Finally, as the season’s middle chapter draws to a close, Damon’s desire to take himself out of the game ramps up as he races to complete unfinished business with Stefan and Bonnie.

With Bonnie's life at stake and an uphill battle ahead of them, Damon and Enzo lead the charge to save Bonnie before her condition worsens. Stefan reluctantly teams up with Matt for the sake of Bonnie and uncovers the truth behind Matt's anger towards him.

Elsewhere, determined to help her best friend, Caroline joins Alaric on a mission and quickly realizes how much she's missed her former supernatural lifestyle. Finally, after their plan takes an unexpected turn, Damon makes a fateful decision that will forever change his relationship with Bonnie.

Despite their best efforts to help Bonnie through the harrowing predicament she now faces, Damon, Enzo and Caroline realize their options are running out and drastic measures need to be taken. With their only chance of saving their friend lying inside the Armory, Stefan breaks the news to Caroline that they may need help from an unlikely source – her and Alaric’s twin daughters.

Elsewhere, Enzo keeps Bonnie preoccupied by bringing her back to their cabin but when his plan takes an unexpected turn, it’ll be up to Damon to make the ultimate sacrifice to save his closest friends.