After learning someone from Stefan's past might be Damon and Enzo's next target, Stefan, Bonnie and Caroline head to North Carolina. While there, Bonnie takes drastic measures in an attempt to break Enzo free of whatever has a hold over him.
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.
Meanwhile Alaric and Stefan try to find out about the origins of what they are up to, Damon is searching for an artifact so he travels to Texas where he encounters Peter Maxwell who leads him to a new revelation.
When her children become the focus of the Siren's latest plan, Caroline (Candice King) takes drastic measures to ensure nothing gets in the way of keeping her family safe. In a race against the clock, Stefan (Paul Wesley) pledges to do everything he can to save the twins, while tensions between Alaric (Matt Davis) and Caroline boil over, leading them to face some harsh realities about the future of their family. Meanwhile, when Enzo (Michael Malarkey) finds himself unable to fight off Sybil's (guest star Nathalie Kelley) latest move, Stefan dives into his subconscious...
Faced with the fallout from his interaction with Cade (guest star Wole Parks), Stefan (Paul Wesley) is determined to have one thing go right - Christmas Eve with Caroline. However, when Damon (Ian Somerhalder) and Sybil (guest star Nathalie Kelley) crash their Christmas Eve dinner, which had been joined by Alaric (Matt Davis), Matt (Zach Roerig) and Peter (guest star Joel Gretsch), things quickly take a dark and twisted turn. Meanwhile, in a series of flashbacks to Stefan's past, Cade's attempt to entice him with his mysterious agenda leaves Stefan faced with an ...
Stefan and Damon attend an anger management support group looking for their next victim. Sybil is still alive and teaching a group of high school students who she'll later use as leverage to get Caroline to locate a historical artifact that can be used against her. Meanwhile, Stefan and Damon continue their commitment to Cade as they test the morals of a young doctor, Tara.
Stefan and Damon return to Mystic Falls at Sybil's request as she is still in search of the historical artifact. Bonnie returns from Paris wearing a vial of Enzo's blood making Caroline wonder if she will become a vampire. Stefan, Damon, Caroline, Bonnie and Enzo all attend the Miss Mystic Falls pageant, where Sybil continues to taunt Damon with memories of Elena.