10. Hell is Other People

Complete story — includes the ending

Three months later, Damon's hell: Amidst Civil War, Damon receives a sad letter from Stefan asking him to return. According to higher orders, in order to take leave, he has to arrest union sympathizers. So he and his friend Henry leave for the mission but end up massacring the host family. As Damon searches the basement, Lily shows up and he realizes it is all fake. Next, Bonnie brings back Damon who wakes up only to realize that Stefan, too, is stuck in hell-world and Julian's held his body hostage. He rushes to a miffed Julian who scorches Stefan's body. Lily shows up again. Damon quickly realizes all this is still hell. He keeps shuttling between the war day and real life, in hell, on a loop unable to save the deserters. Eventually, under the influence of Stefan, Damon realizes that his messed up life basically roots down to him escaping guilt after having missed his mother when he needed her the most. Finally, Damon returns to the very first vision of hell he had and finds Lily in excruciating pain. Overwhelmed by emotions, Damon starts sobbing and saying that he missed her and how angry he was at himself for not bidding her goodbye the way she deserved in the last two chances. He begs her to give him one last chance to serve her and receive her love but death intervenes. Lily dies in his arms and Damon is left devastated. This time he actually escapes hell, unable to believe that he lost his mother again and begs Bonnie to send him back. As Stefan tries explaining to him that all of it was hell faux, he loses it completely and goes on an attacking spree over Stefan, Caroline, Matt and Bonnie. As the episode ends, Damon is mentally and emotionally drained as he staggers to stand still, looking around and realizing that this time it was real.