When Alaric realizes that Jo can’t be compelled, he asks Elena to do some digging into her background. After learning that Enzo has been captured by Tripp, 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 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.

Determined to celebrate Bonnie’s birthday, Elena convinces Jeremy that it’s what Bonnie would have wanted. After piecing the broken ascendant back together, Elena, Jeremy and Damon attempt to send Bonnie a message, but the situation turns dire when they make an unsettling discovery. Meanwhile, after uncovering Stefan’s secret about his great-niece Sarah Salvatore, Enzo enlists a reluctant Matt to help interfere with her life. Elsewhere, Stefan keeps a close eye on Caroline as she unconventionally attempts to cope with everything going on around her. Lastly, realizing it might be time to move on with his life, Jeremy contemplates leaving Mystic Falls for good.

In order to get through to Lily about Julian's manipulating ways, Stefan and Damon confront their mother with painful memories from their childhood. However, when Lily reveals a dark secret she's been harboring for over 160 years, Stefan and Damon are left questioning everything they've ever known about their family. Determined to prove himself to Lily, Enzo comes face-to-face with Julian and challenges him to a duel, but an unexpected twist threatens to complicate things.

Elsewhere, Matt finds himself in the middle of a deepening mystery involving the residents of Mystic Falls, and Caroline's world is turned upside down when Valerie reveals some life-changing news to her.

When complications from her supernatural pregnancy leave Caroline's life hanging in the balance, Stefan and Valerie take extreme measures to try and save her and the babies. Meanwhile, after uncovering a dark secret about Damon, Enzo uses the information to force Damon into helping him track down Rayna Cruz, a ruthless vampire hunter who is on the loose. However, when Damon's actions inadvertently put everyone he loves in Rayna's path, he is forced to make things right before it's too late.

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.

As Enzo continues to fight the control over him, Bonnie finds herself at the center of a deadly game and forced to make a heart wrenching decision involving two of the most important people in her life. At the Armory, Alaric researches a mysterious artifact that he hopes will help in their fight to get Damon and Enzo back. Finally, Damon’s downward spiral leads him to Tyler Lockwood who attempts to talk some sense into him before it’s too late.

In order to save Stefan’s soul, Damon makes a deal with Cade to retrieve the Maxwell journal. Alaric and Matt refuse to hand the journal over as it may contain the key to destroying Cade. Caroline desperately tries to connect with Stefan before Cade goes through with his plan.