Sam check on the injured Bobby while Dean drives to the hospital.
Bobby is in the woods with Sam and Dean and they find a corpse strung up from a tree. He realizes that his head is bleeding and that something is wrong, and they go back to the cabin. Bobby tries to explain and realizes that there are numbers that he has to tell them that relate to the Leviathans' plan. When Bobby looks, up, he's in a bedroom holding a glass of wine and his wife Karen is on the bed. He realizes that it's another vision from his past, and Karen asks him to sit so she can tell him something. When he does so, Bobby realizes what night it is. A storm booms outside and he looks outside and sees the sky darken and the moon go out. A young boy runs toward the house and Bobby tells Karen that he has to go.
Outside, Bobby finds Rufus, dressed as a pest-control worker outside a church. He tries to tell Rufus that he's going to die, but Rufus goes into a house as the young boy runs past again. He comes back and grabs Bobby's arm, and says that God is going to punish him. A glass breaks behind Bobby and when he turns back, the boy is gone. Bobby goes inside and finds a church choir gathered. The church shakes and the choir members disappear, and then the lights go out row by row. A man comes in behind him, dressed in a black suit, and tells him that his time is up. Bobby realizes that the man is a Reaper, and the Reaper explains that Bobby is in a coma and that he had to enter his dream to get him. Bobby runs off and the Reaper warns him that he's prolonging the inevitable.
Bobby finds himself in his homeand finds Sam and Dean arguing about Chuck Norris vs. Jet Li. He ignores them and goes to the kitchen, and finds a woman setting the dinner table. She says that Bobby is filthy and asks why he wants "him" to get mad. Bobby then finds himself back at the church with Rufus, hunting Lara Coggins, a ghost who is killing men who break girls' hearts. As Rufus prepares to open the coffin, Bobby tries to explain what's happening to him. Rufus ignores him and breaks open the coffin...
Dean and Sam watch as the ER doctors work on Bobby. The nurse warns them that they can't get the bullet out until the swelling goes down.
In the crypt, Lara attacks Bobby, calling him a heart breaker, and rams her hand into his chest.
The brothers watch as Bobby crashes.
Rufus uses cold iron on Lara, temporarily dissipating her. She attacks Rufus, but Bobby salts and burns her bones, destroying her ghost. He tells the unconscious Rufus that he needs him and then carries him off.
A doctor finally tells the brothers that Bobby is stable and now they can only wait.
Bobby finds himself on a street in daylight. He sees the kid again and goes over to him, and then realizes that he knows who he is. The nurse brings Rufus out of the nearby hospital and the boy disappears. Bobby asks him what he saw during his near-death experience, and Rufus says that he saw the apartment building from when he was a kid, and he tried to get out by looking for the exit door. Every door he opened lead to another memory, and he finally went deep into the things he didn't want to think about to get out. Rufus wonders what Bobby is going about and he explains that he's in a coma and has to get the numbers to the Winchesters.
The storm starts rolling in and Bobby tells Rufus that he needs him, his partner, to come with him. When Rufus tells him to focus on his worst memory, Bobby says that he has too many to narrow things down. However, Rufus asks him why the ghost called him a heartbreaker and Bobby realizes what memory he needs to face. He finds himself facing Karen, who asks why he refuses to be with her. She accuses him of refusing to have children with her, breaking his heart, and tells him to go away, and Bobby apologizes, saying he never stopped being sorry. He then tells Rufus that Karen was possessed three days later, and his biggest regret was fighting with her. Rufus tells Bobby to try the door now, and Bobby thanks him before going to the door.
Bobby steps through and finds himself with Rufus, watching his younger self with Young Dean in 1989. He plays ball with the boy, and Rufus points out that Bobby makes a heck of a dad. Bobby tells him to shut up and looks around for another door. As they find one and approach it, Rufus asks why Bobby doesn't want kids. Bobby explains that his dad was a mean drunk and didn't want to pass on the legacy, and Rufus tells him that he needs to accept whatever it is that he's trying to avoid.
They go through the door and find themselves in Bobby's childhood home. His mother nervously serves supper and the boy, Young Bobby, knocks over a milk glass. His father Ed accuses him of breaking everything he touches, takes a drink, and throws his plate off the table when his wife tries to intervene. Bobby steps forward and closes the door, and then tells Rufus that he's sure he's in the wrong place. The storm grows closer and Rufus warns Bobby that the Reaper is getting closer and there's no way to stop it. Bobby realizes what he has to do and says that they're going to stop the Reaper.
The doctor tells the brothers that only one hemisphere of Bobby's brain was damaged, but says that more often than not the patient dies. It all comes down to Bobby. After the doctor leaves, an insurance representative comes in and asks if one of them is Bobby's next of kin. He talks to Dean and asks if Bobby was listed as an organ donor. Dean insists that Bobby won't die and that he'll be fine because he's always fine, and punches the wall behind the insurance representative. He tells the man to walk away and he does, and then Dean goes outside. He sees Dick parked outside and dares him to come out and finish the job. As people gather and start taking photos, Dean reminds him that he's in a high-profile body. Dick tells him to check Bobby because he's a good shot. When he laughs, Dean tells him that he's coming for him and goes back inside.
Bobby goes to his home and looks for a King James Bible. He then tells Rufus that it's impossible to stop a Reaper, but he can slow them down. He finds a cross and rosary in a compartment in the Bible and takes it out.
Dean tells Sam about his encounter with Dick and asks for an update, and Sam says the swelling is down and Bobby is still fighting. However, he warns his brother that the doctors aren't going to try taking the bullet out, but may cut out the injured brain tissue. He then tells Dean that they need to brace themselves for Bobby's death. Dean refuses to accept it and says that they've been through enough, and then walks away.
Bobby and Rufus prepare a ritual, but Bobby discovers that most of his ingredients are missing. As he goes through a drawer filled with objects, he sees his younger self on the phone talking to John, saying that the brothers need their father around. When Bobby turns back to the drawer, he discovers that it's empty. He goes back to the living room and inscribes a sigil on the floor, and then holds the cross and begins the ritual. The Reaper appears within the sigil and admits that he's impressed, and then tells Bobby that the dark is coming and Bobby knows it. Bobby looks around and realizes that things are disappearing as the bullet kills parts of his brain. The Reaper invites him to come with him, saying that he's earned it. Rufus asks Bobby if he wants to be stuck as a ghost, and the Reaper says that Bobby has helped with his small, meaningless night, and that he's done enough. Bobby refuses to accept that, saying that the Winchesters are his boys. He sees the young boy again, his younger self, and realizes that the only way out is through. He thanks Rufus and then follows the boy out.
Bobby is back at his childhood home, and watches as his mother cleans up the broken glass. Ed tells Young Bobby to help clean. When the boy leaves the room, Ed complains that his wife lets their son do whatever he wants. As Young Bobby comes back, Ed hits his mother and Young Bobby runs out of the room. When Bobby's mother wonders why her husband provokes his son, Bobby speaks up, saying that's a load of crap, and calls him a drunken bully. Ed says that he breaks everything that he touches, and Bobby tells him that he adopted two boys and they grew up heroes, and Ed can go to hell.
The ER nurse tells the brothers that Bobby is starting to respond and that they if they want to see him, they have to do it quickly.
Young Bobby comes back with a rifle and his father laughs. His father says that he's not man enough to use it and then grabs his wife by the hair. Young Bobby shoots him in the head and his mother, shocked, says that God will punish him. Bobby tells his younger self that he did what he had to, and this is the point where he learns that even when you save people, you don't save them. He then tells his younger self to get a shovel and bury his father behind the woodshed, the same as the first time. The Reaper appears behind him and points out that he has a genetic case of bullet to the brain. Bobby runs to the door and opens it, and goes into the light beyond.
As the doctors prepare Bobby for surgery, Sam takes his hand and thanks him for everything. Bobby opens his eyes and tries to talk. The brothers give him a pen and he writes the numbers on Sam's hand. Once he's done, he calls them "idjits," smiles, and then flatlines. The doctors take him to the trauma room
Bobby finds himself back at his house. As he gets beers for the brothers, the Reaper appears and congratulates him on managing to wake up. He then explains that it's dark outside because everything else in Bobby's brain has been destroyed by the bullet. The Reaper tells Bobby that for his own good, he should move on, and assures him that the Winchesters will be okay without him. Bobby considers and then says he's glad he saved the best memory for last. He goes in and watches as Dean and Sam banter back and forth. They fade away and the Reaper asks Bobby if he's going to stay or go.