S6, E15: After assigning tasks to each of her friends, Caroline attempts to deal with her current situation as reality begins to set in around her. Elena spends a day with Caroline and grows concerned when she starts noticing a strange change in Caroline’s behavior. Meanwhile, Alaric becomes wary when Kai (recurring guest star Chris Wood), who has begun experiencing unexpected consequences from the merge, turns to Jo (recurring guest star Jodi Lyn O’Keefe), 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.