Damon wakes up in 1863. He is not a vampire, just a soldier in the Civil War. Lily is standing there alive. That should have been a clue something was going on, but he goes about his day. He saves a fellow soldier named Henry, he wakes in a medical tent, and gets a dramatic letter from Stefan about how their father isn’t handling their mother’s death well.
To go help Stefan, Damon asks for leave. His superior says no, but Damon says he will do whatever he has to do to get the leave. His superior says he can go if can bring back a couple of deserters from a nearby town. Damon and Henry head to the house where three women let them in for dinner. But the two deserters come out shooting and everyone ends up dead except Damon.
Damon hears a noise in the cellar and goes to check on it. It’s his mother–alive. She tells him that his spirit is in the Phoenix Stone and that this is hies punishment. She shoots him and he wakes up to Bonnie.
Bonnie pulled Damon out of the prison world first. But Julian stole Stefan’s body while she was distracted. While she does a locator spell to find him, Caroline explains they pulled Damon out first because the longer you’re spirit is in the Phoenix Stone, the more of it you lose. They didn’t want Damon to lose too much that when he came out he would kill Bonnie to bring back Elena.
Bonnie’s locator spell works, so Damon goes to meet Julian at a diner on Route 29. Julian has Stefan’s body soaked in gasoline. He explains that resisting the pain when you’re in the Phoenix Stone just makes it worse. Then he throws a lighter onto Stefan’s body. As Stefan’s body goes up in flames, Damon sees his mother again. She says “the pain is real, the feeling is real” before he wakes up in the medic bed.
Re-living The Day
Damon is re-living this day in the prison world and thinking he escapes it on repeat. He tells Henry what to do at the farmhouse. They gather up the women so the men won’t shoot them. They shoot them anyways. Damon wakes up with Bonnie again, but Stefan was pulled out before him. Damon stabs his brother.
In the real present, it turns out that they did pull Stefan out first, but they are struggling to pull Damon out. Stefan says that the only way they were able to reunite his soul with his body is because he gave into the pain. But that doesn’t sound very Damon-like.
Damon tries various ways of trying to kill the deserters until he gives up. He decides the quickest way to get to Stefan is to become a deserter himself. He tries to head to Mystic Falls, but ends up at the house anyways. Lily is inside as well as Stefan and Elena’s coffin. Stefan tells Damon he can’t tell right from wrong without Elena. Stefan keeps jabbing at him until Damon admits the day of the farmhouse massacre it wasn’t Stefan he wanted to see–it was his mom.
Damon wakes up in the forest, but this time Lily is under the wheel, not Henry. She wants him to save her, but he says it isn’t real and doesn’t matter. She recites, “the pain is real, the feeling is real”. Instead of saving her, Damon finally confronts his feelings about his mother. He says what he should have told her when she was dying.
This feeling was enough for Damon to be united to his spirit. He wakes up to Bonnie, Stefan, Caroline and Matt. But doesn’t think it’s real and stakes Caroline and Stefan and knocks out Matt and Bonnie. He looks around and wonders why he is still there when it isn’t real.