Lane Miller

After shutting off her humanity following the death of her mother, Caroline gives her friends an unexpected ultimatum. Not knowing how to handle the new Caroline, Stefan's attempt to intervene sets off a dangerous chain of events, leaving him and Elena in a race against the clock. Meanwhile, after seeking answers from Kai (recurring guest star Chris Wood) about the prison world, Damon's world is turned upside down when he learns some devastating news about his mother, Lily (recurring guest star Annie Wersching – 24). Elsewhere, Enzo finds himself becoming increasingly intrigued by Sarah Salvatore (recurring guest star Tristan Mays), and Bonnie begins to struggle with the effects of being back in the real world.

With their humanity turned off, Stefan and Caroline begin wreaking havoc at Whitmore, leaving Damon to come up with a risky plan involving Lily (recurring guest star Annie Wersching). After rushing to help Jo (recurring guest star Jodi Lyn O'Keefe) treat victims of Stefan and Caroline's latest killing spree, Elena discovers Jo is pregnant, prompting her to reevaluate her own life as a vampire. Meanwhile, when Sarah (recurring guest star Tristin Mays) boldly turns the tables on an unsuspecting Enzo, he is forced to open up about his tragic past. Lastly, at Scull Bar, a twisted round of karaoke leaves Tyler and Matt in a dangerous situation.

Blue helps Keira prepare for an audition, resulting in an intimate "first" moment for the couple. Tasha tells Rick her intentions to break things off with Pookie but she is caught off guard by an impromptu proposal.