Stefan searches tirelessly for Damon and Enzo months after their mysterious disappearance.

No one can accept the loss of Damons humanity that Enzo hopes for too, Damon carelessly tries to prove everyone wrong.

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.

Stefan and the others remember what matters most when tragedy strikes close to home.

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 and along the way, sets off a chain of events that leaves him faced with a life-changing decision.

Faced with the fallout from his interaction with Cade (Wolè Parks), Stefan (Paul Wesley) is determined to have one thing go right - Christmas Eve with Caroline. However, when Damon (Ian Somerhalder) and Sybil (Nathalie Kelley) crash their Christmas Eve dinner, which had been joined by Alaric (Matt Davis), Matt (Zach Roerig) and Peter (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 unimaginable decision. Kat Graham and Michael Malarkey also star.

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.

Mystic falls is greeted by a traditional celebration and also two reckless brothers. Caroline remains in denial about the future.

Sybil puts Damon in a catatonic state for revenge. Caroline and Bonnie enter Damon's mind and realize Stefan is the key to his fate. Sybil competes with her sister for control of the bell.

Cade returns to Mystic Falls with new assignments for Damon and Stefan that each lead to unthinkable consequences.

Damon makes a deal with Cade to retrieve the Maxwell journal in exchange for Stefan's soul.

Damon and Alaric face an old enemy after finding a weapon that might kill Cade. Stefan is captured by someone from his past. Bonnie tries to reach out to Enzo through Cade.

Damon and Stefan join forces against Cade to protect Elena's casket, while Caroline and Alaric cope with their daughters' growing powers.

A wedding is quickly planned in order for Damon and Stefan to lure a dangerous enemy out into the open.

With the fate of Mystic Falls at stake, Stefan and Damon must fight their greatest enemy for one last battle.