After assigning tasks to each of her friends, Caroline attempts to deal with her current situation as reality begins to set in around her. While spending the day with Caroline, Elena grows concerned when she starts noticing a strange change in her behavior. Meanwhile, Alaric becomes wary when Kai, who has begun experiencing unexpected consequences from the merge, turns to Jo, desperate for her help. Elsewhere, while Bonnie finds herself in an unfamiliar situation, Matt and Tyler contemplate a major life change. And when Damon offers Caroline advice on how to cope with everything going on around her, it forces him to revisit painful memories involving his own mother.

With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon's mother Lily, who is trapped in the 1903 prison world. Meanwhile, when Caroline's plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric's attempt to reel Caroline back in doesn't quite go as planned when they realize they're outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.