Original air date: 02/05/2016 Runtime: 42:26 min. 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 (recurring guest star TODD LASANCE) and his men take over Mystic Falls, leading Matt to spiral out of control and into trouble with an officer named Penny (recurring guest star ANA NOGUEIRA). Meanwhile, Tyler (guest star MICHAEL TREVINO) returns to town for Alaric’s baby shower and Caroline makes an upsetting discovery involving Alaric and his future plan for the babies.
Original air date: 04/15/2016 Runtime: 42:27 min. Determined to capture an escaped vampire named Ambrose, who may be the key to getting Stefan back safely, Damon heads to Memphis with Alaric in tow. However, reluctant to step back into his former vampire-hunting ways, Alaric makes his unwillingness to participate clear, while revealing the truth about the past three years of his life without Damon. Meanwhile, in the psych ward, Bonnie meets a young woman named Virginia (guest star AISHA DURAN), who provides her with some valuable information about why The Armory may be after her. Finally, Enzo takes matters into his own hands when he learns some devastating news from Rayna (recurring guest star LESLIE-ANNE HUFF).
Original air date: 04/22/2016 Runtime: 42:22 min. When Enzo’s efforts to protect Bonnie end up putting her life in jeopardy, it is learned that Rayna (recurring guest star LESLIE ANNE-HUFF) may hold the key to her survival. With time running out and Rayna at the reins, Enzo and Bonnie reluctantly team up with Damon, who is desperate to save Bonnie’s life and to repair their broken friendship. Elsewhere, when Stefan travels to Dallas and comes face to face with Alaric, tensions escalate and they are forced to confront the fallout from Stefan’s absence in Caroline’s life. Finally, Enzo learns The Armory’s true motives behind their search for Bonnie.
Original air date: 04/29/2016 Runtime: 42:28 min. 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.
Original air date: 05/06/2016 Runtime: 42:24 min. When Damon’s risky attempt to save Bonnie takes an unexpected turn, the consequences of his actions forces everyone to band together to help her pull through. Meanwhile, when a new threat leaves Caroline’s life in jeopardy, Stefan makes a rash decision that ultimately forces them to face the fallout from their relationship. Elsewhere, Enzo tries to hold it together as he painfully watches Bonnie in the fight of her life, while Matt takes matters into his own hands to save one of his closest friends.