Sam and Dean drive the injured Bobby to the hospital.
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Bobby finds himself in the forest with Sam and Dean, hunting down the New Jersey Devil. As they come to the ranger’s corpse, Bobby realizes that something is wrong and discovers that he’s bleeding from his head. He tells them that something bad is going to happen… or it’s happened already. They go back to the cabin and the brothers ask what’s wrong. He tells them that he’s been shot in the head in the real world. They have no idea what he’s talking about buy Bobby says that there’s something he has to tell them, a series of numbers. He goes to find a piece of paper and write them down, explaining that it’s important to the Leviathans’ plans.
When Bobby turns around he finds himself in a bedroom facing his wife, Karen. She’s in bed and Bobby has a glass of wine in his hand. Bobby steps forward and gives it to her, and realizes that it’s just like how it was the first time. Karen starts to say something, telling him to sit and listen. He does so and Bobby realizes what night it is and what she’s going to say. A storm gathers outside and he looks outside. A young boy is on the yard outside, running toward the house. Bobby tells Karen that he has to go and apologizes.
Bobby goes out through the door and finds himself with Rufus outside a church. They’re dressed as pest-control workers and on a mission. Bobby tries to explain that he’s going to die but Rufus goes into the church. The young boy runs past while Rufus calls to him to come in. When Bobby turns back, the boy takes his hand and says that God is going to punish him. A glass of milk shatters behind Bobby, and when he turns back the boy has disappeared.
Inside the church, choir members have gathered but they disappear as the building shakes. The lights in the church shut off and a man in a black suit appears behind Bobby. He tells Bobby that his time is up, and Bobby realizes that the “man” is a Reaper. The Reaper explains that since Bobby is in a coma, he had to come in to get him. Bobby runs off and the Reaper calls out that he can find him anywhere and that Bobby is only prolonging the inevitable.
Bobby finds himself in his home, listening to Dean and Sam argue Jet Li versus Chuck Norris. They turn to Bobby to adjudicate but he goes to the kitchen. A woman is setting the dinner for table, and warns Bobby that he needs to clean up or he’ll get “him” angry.
The scene changes and Bobby is in the church crypt. Rufus explains that the ghost, Lara Coggins, they’re dealing with was left at the altar and killed herself, and now she kills men who break women’s hearts. Bobby tries to explain but Rufus ignores him and breaks open Lara’s mausoleum.
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The ER staff treats Bobby and usher the brothers out. The nurse warns that they may not be able to get the bullet out.
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Rufus opens the coffin but Bobby says that he needs to keep moving. Lara’s ghost appears and calls him a heartbreaker, and rams her hand into Bobby’s chest.
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The doctors try to stabilize Bobby.
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Rufus dissipates the ghost with cold iron. She reassembles and attacks him, and Bobby salts and burns her bones. He realizes that he needs Rufus and hauls him out.
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The doctor tells Dean and Sam that they’ve stabilized Bobby for the moment, but they’ll have to wait and see if he recovers.
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Bobby finds himself outside a hospital, and sees the young boy watching him. He finally recognizes the boy. A nurse brings Rufus out in a wheelchair and the boy disappears. Bobby asks Rufus about his near-death experience. Rufus explains that he saw the apartment building from when he was a kid and that he tried to find an exit door. Every time he opened a door, there was another chapter of his life on the other side. He finally went deep to his most frightening memory, the one he didn’t ever want to go to. Bobby explains that he’s in a coma and needs to find the right door to get the numbers to Sam and Dean. The imaginary Rufus is understandably skeptical that he’s just a memory. The storm moves in and Bobby tells Rufus that he needs him, and Rufus agrees.
As they walk down the street, Rufus tells Bobby to focus and then asks why Lara called him a heartbreaker. Bobby realizes what his worst memory could be and goes through a door. Karen is on the other side, back in the bedroom, saying that she hates him and that their life together is a lie. She asks why he never told her that he refuses to have children, and asks why he thinks that he breaks everything he touches. Karen backs away, stepping on the shattered glass. Bobby says that he’s sorry and never stopped being sorry. Rufus asks why he doesn’t want children, and Bobby explains that Karen was possessed three days after their confrontation. The biggest regret of his life was never being able to get past the conversation, and if he had known Karen was going to die then he would have said whatever she wanted to hear. Rufus tells him to try the door now.
Bobby steps through the door and finds himself in 1989 with Rufus. The younger Bobby is with Young Dean, playing baseball in a park rather than practicing shotgun shooting. Young Bobby explains that they’re going to play baseball like a normal father and son, and Rufus points out that Bobby makes a good dad. They spot another door nearby and go to it, and Rufus asks why Bobby didn’t want kids. Bobby explains that his father was a mean drunk and he didn’t want to pass on a legacy. Rufus warns that Bobby is avoiding the issue but Bobby insists he doesn’t know what it is he doesn’t want himself to know.
Bobby goes through the door and finds himself back in the kitchen with the woman. She’s serving dinner to her husband and the boy, Young Bobby, runs in. His father Ed insults him and asks for the biscuits, and Young Bobby spills a glass of milk on the floor. Ed tells him that he breaks everything that he touches. When his wife says they should have a nice supper, Ed throws his plate on the floor. Bobby closes the door and tells Rufus that the memory was just another normal life. Rufus doesn’t believe him but Bobby says that they’re in the wrong place. The world shakes again and Rufus warns that the Reaper will catch up. Bobby gets an idea and goes into his house, saying that they’ll stop the Reaper.
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The doctor tells the Winchesters that the bullet didn’t shatter and Bobby has a chance, but doesn’t want to give them false hope. An insurance representative comes in and talks to Dean privately, asking if Bobby is registered as an organ donor. Dean refuses to discuss the matter, insisting that Bobby will be fine because he’s always been fine. He hits a nearby sign in frustration and tells the representative to walk away.
Dean goes outside for some fresh air and sees Dick Roman the Leviathan parked outside. Dick boasts that he’s a good shot and that Bobby doesn’t have long, but Dean calls him out and warns that since he’s in a public figure, people will see and report. Dick stays in his car and Dean warns him that they’re coming for him and he’ll wish he could die.
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Bobby searches his library for a King James Bible and tells Rufus that a Reaper can’t be killed, but it can be stopped. He finds the Bible and the cross inside of it.
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Dean tells Sam that he saw Dick, and Sam tells his brother that Bobby is still fighting for his life. However, he warns Dean that the doctors are considering removing the damaged brain tissue and that they need to expect the worse. Dean insists that they’ve been through enough and walks away.
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As Bobby goes through his house looking for spell components, he discovers that things are disappearing one by one. He goes to the kitchen and sees his younger adult self on the phone with John Winchester, telling him that he played baseball with Dean and that the brothers are entitled. Bobby and Rufus complete the spell and draw a binding circle on the floor. When they cast the ritual using the cross, the Reaper is trapped inside. He tells Bobby that he’s trying to help him because Bobby will die no matter what. The disappearances are Bobby’s memories, fading one by one. Bobby looks around and realizes that the objects in his home are fading away. The Reaper warns him that once the room fades from Bobby’s memories, he’ll be free. He invites Bobby to come with him and be done. Rufus points out that if Bobby dies and gets stuck, he’ll become a ghost and a hunter will kill him. The Reaper assures him that he’s done enough and accomplished major things when he should have died of liver disease. Bobby refuses to accept that, insisting that Sam and Dean are his boys. Young Bobby appears in the room and Bobby says that the only way out is through, and tells his younger self to lead the way. He tells Rufus it’s been good seeing him again and leaves.
Bobby follows his younger self back to the kitchen where his mother is still cleaning up the broken glass. Ed tells Young Bobby to get a broom and the boy runs out of the room, and then the father tells his wife that she lets Young Bobby do whatever he wants. When she suggests he have another drink, Ed tells her not to tell him what to do. As Young Bobby comes back, Ed slaps his wife and she asks why he keeps provoking Young Bobby. Ed says that he’s a bad kid and looks at Bobby. Bobby says that it’s a load of crap and Ed demands that Bobby show his father respect. He insists that Bobby deserved to be beaten, but Bobby says that he respect is earned. When Ed says that Bobby broke everything he touched, Bobby tells him that he adopted two boys and they grew up to be heroes.
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The ER nurse tells Dean and Sam that Bobby is starting to recover and they’re taking him to surgery. She tells them to see Bobby quickly if they need to.
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Mrs. Singer pleads with her husband, begging his forgiveness, and Young Bobby comes in with a rifle. Ed laughs and says that he’s not man enough to shoot, and tells him that he’ll deal with him late. When he grabs his wife by the hair and yanks her up, Young Bobby shoots him in the head, killing him. Miss Singer stares in shock and then tells her son that God will punish him. Bobby tells his younger self that he did what he had to do, and this is where he learns that saving people never really saves them. He then tells Young Bobby to bury Ed behind the woodshed. The Reaper, freed, comes in and Bobby runs out the door and into the light.
As Sam and Dean stand at Bobby’s bedside, he wakes up and grabs Sam’s hand. He can’t speak and gestures for a pen, and then writes the numbers on Sam’s hand. Once he’s passed on the information, he smiles at the boys, says “Idjits,” and then flatlines.
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Bobby finds himself back in the memories of his house. As he gets beers for Sam and Dean, the Reaper congratulates him on managing to wake up. He warns Bobby that everything else is dark because all of Bobby’s other memories have been destroyed by brain damage from the bullet. The Reaper tells Bobby its his last chance to move on, for his own good, and assures Bobby that the Winchesters will be okay without him. When Bobby realizes that it’s his last memory, he says he’s glad he saved the best for last. He takes the beers to the brothers, who haggle about licorice and then fade out. The Reaper asks Bobby if he’s going to stay or go.
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