Stefan and Elena experience unsettling dreams of the life they might have had together. Bonnie has a disturbing encounter with Grams. Enzo searches for a woman he loved decades ago. Bonnie learns that Jeremy is working with Liv. Matt has a terrifying encounter with inhabitants of the Other Side.

More powerful than ever, Kai holds Elena captive while he learns to control his newly acquired magic. At the Salvatore mansion, Liv and Alaric try to prepare Jo for the impending merge ceremony with Kai, but they quickly realize Jo is weaker than they thought. After bringing Sheriff Forbes home from the hospital, Caroline travels with Stefan to North Carolina in search of a cure for her mother's cancer. Meanwhile, Stefan, who has his own intentions for traveling to North Carolina, is caught off guard when Enzo shows up demanding to know what Stefan is hiding. Lastly, when Damon discovers Elena has been kidnapped by Kai, he is forced to rethink his strategy after an unexpected visitor throws a wrench into his plan.

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 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 watch Bonnie in the fight of her life, while Matt takes matters into his own hands to save one of his closest friends.

When her children become the focus of the Siren’s latest plan, Caroline takes drastic measures to ensure nothing gets in the way of keeping her family safe. In a race against the clock, Stefan pledges to do everything he can to save the twins, while tensions between Alaric and Caroline boil over, leading them to face some harsh realities about the future of their family. Meanwhile, when Enzo finds himself unable to fight off Sybil’s latest move, Stefan dives into his subconscious and along the way, sets off a chain of events that leaves him faced with a life-changing decision.