In Hurleyville, New York, two young boys run to a barn as someone chases them. They duck inside and hide, and another boy, Timmy, comes in and says that the barn is off-limits for hide-and-seek. An older man, Jack, come in and tells them that it's bedtime, and notice the temperature drop suddenly. He gives them to the count of ten to come out, and then his flashlight flickers and goes off. A tractor stops and shifts into gear on its own, and drives directly toward Jack, running him through and pinning him to the barn doors.
At the Letters HQ, Sam calls to Dean and Kevin but gets no answer. He starts to settle down with a book, but Dean's cellphone rings. Sam reluctantly answers it and the caller asks for "D-Dawg." Dean, coming in, overhears the conversation, take the phone, refers to the caller as Sonny, and says that he'll be there as soon as he can. Sam wonders what's going on and Dean reminds him of the time when they were kids and he disappeared for a couple of months. John told Sam that Dean disappeared on a hunt, but Dean explains that he lost the food money John left them so he went for good, was arrested, and sent to a boy's home. Sonny ran the place and knows what they do, and Dean gave him his number if something supernatural came up. As he heads out, Dean asks Sam if he's okay to travel, and then asks if "everyone" is okay to leave. Sam has no idea what he's talking about and Dean tells him to head out. As they go, Sam asks why Dean didn't tell him about the incident and Dean says that John told him not to and he never thought to say anything since.
As the brothers arrive at Sonny's house, Sam wonders why John didn't find him. Dean explains that John left him there as punishment for two months because he had a mistake. As they go up to the front door, a boy watches them from an upstairs window. Meanwhile, an older woman, Ruth, answers the door and she reluctantly lets them in and asks if they know Sonny from prison. Ruth goes to get Sonny while Dean and Sam go inside, and Dean remembers how he ended up there.
A deputy, Billy, drops Dean off at the house and tells Sonny that he was stealing peanut butter and bread. John told them to let Dean rot in jail so Billy brought him to Sonny. Sonny notices that the deputy has a black eye and Dean snickers. Billy starts to go for Dean but Sonny stops him. Once Billy leaves, Sonny points out that the deputy left with the key. Sonny easily gets them open with a paper clip and notices scratches on Dean's wrist. Dean says that a werewolf clawed him and Sonny accepts his story without comment. Dean wonders why Sonny thinks he won't run away, and Sonny points out that he stole food so he doesn't have anywhere to go. He explains that kids work there and get some discipline, and that it beats jail.
Sonny comes in and greets Dean. He admits that they only have a few boys there because the system incarcerates them instead of sending them away. As Ruth cleans up around the place, Sam suggests that they talk privately and Sonny sends her to check on the boys. Once she leaves, Sonny explains that Jack was killed by a tractor even though it doesn't work. He figures that something isn't right, and says that lights have been flickering and windows and doors are slamming shut on their own. Sonny tells them that most of the boys are gone for break, and Dean goes out to check the barn while Sam checks the house.
Sam checks out the bedrooms and finds one bed with Dean's name on it beneath a layer of nametags. He hears something moving in the next room and draws a knife, and then goes in to check on it. He finds Ruth kneeling at her bed, praying. Sam apologizes and Ruth asks if he saw a ghost. She says that she knows why the Winchesters are really there and is praying for the ghost haunting the farm to leave.
Dean checks out the barn and scans for electromagnetic activity. He hears boys laughing and goes into the next room to investigate. A boy steps out of the shadows to confront him. When Dean wonders what he's doing, the boy says that he's fighting monsters and holds up an action figure. The boy introduces himself as Timmy gives him a hesitant handshake. Dean shows him how to shake like a man and asks about Jack, and Timmy explains that he and the other boys were playing there when Jack died. The boy describes how it got cold suddenly, and then goes off to do his chores.
Ruth tells Sam that she grew up in the town and knew the farm's original owners, Howard and Doreen Wasserlauf . Jack worked there as a farmhand and a drunken Howard got the idea that Jack and Doreen were having an affair. He tried to kill them both with a meat cleaver and got life in jail when he killed Doreen but Jack escaped. Howard died in prison a year ago and Ruth figures that his ghost got revenge on Jack.
That night, Sam and Dean go to the cemetery and dig up Howard's grave. Sam wants to know more about Dean's time there, and Dean insists that it wasn't that bad. They open Howard's coffin, salt the bones, and set them on fire.
The next day at the house, Ruth is taking a bath when the lights flicker and the temperature drops. The shower curtain comes down on Ruth, asphyxiating her, and Sonny hears her struggling. He tries to break down the door without success while Ruth dies.
Dean and Sam stop at a restaurant in town, and Dean notices the waitress.
Sonny takes Dean to the restaurant after a month, and Dean thanks him for getting the charges dropped. Much to Dean's surprise, Sonny says that he can stay there as long as he wants and that he's proud of him for doing well at school. He then asks why Dean has a few occult symbols carved on his bedpost and puts down a salt line. Dean doesn't want to talk about it, saying that it's a family thing, and sonny points out that his family left him there. Despite that, Dean still refuses to discuss it. Sonny talks about how he was in a gang, but his loyalty got him in prison for 15 years. He tells Dean that the important thing is to be loyal to oneself. A young girl, Robin, comes over to get their order.
Robin comes over to get Sam and Dean's order. She doesn't recognize Dean until he introduces himself, and even then it takes a minute. Dean points out that she used to come up with her mom, who gave him guitar lessons. Once she leaves, Dean gets up and tells Sam that they're going. Outside, Sam wonders what's going on but Dean insists that it's nothing. Sonny calls and tells them that Ruth is dead.
At the farm, Sonny tells the Winchesters what happened as the EMTs take Ruth's body away. Dean asks Sonny if he remembers anything else unusual, and he says that Ruth's rosary beads are missing. Dean goes to chat with the boys while Sam and Sonny go over the employee records.
Dean finds two of the bigger boys picking on Timmy. He breaks it up and asks where they were. They confirm that they were running errands in town and say that the only thing weird at the farm is Timmy. Dean tells them not to touch the boy again and they run off. He then tells Timmy that bullies are cowards and they'll stop if he stands up to them.
As Sam and Sonny go into the house, Sam notices a wall filled with ribbons and awards. Sonny explains that they've had some talented athletes, including Dean, who was a wrestling champion.
The two bullies are working in the yard when Robin pulls up to give guitar lessons. As she goes inside, one of the boys snags Ruth's rosary beads on his lawnmower. He reaches in to pull it out, while Timmy watches from upstairs. Neither bully notices as the lever on the lawnmower moves on its own, and the boy screams in agony. Upstairs, a ghostly figure puts a reassuring hand on Timmy's shoulder.
Dean takes the bully to the hospital and then returns to the farm. Sam confirms that the bully was picking on Timmy, and shows Dean the file confirming that Timmy was found in an abandoned building a year ago. The parents never showed up and Timmy kept running away from orphanages, so Sonny took him in three months ago. Sam figures that it's ghostly possession and they split up to search for the boy. Sam goes to the barn and checks out the crawlspace. He discovers that Timmy has drawn pictures of his parents dying in a burning car crash.
In the house, Dean hears Robin playing and goes into the room where she's tuning up.
A young Robin shows Dean how to play and he talks about how his dad likes to move around a lot. He admits that he doesn't like it but John expects him to follow in his footsteps. Robin says that she feels the same thing and asks what he really wants to do. She wants to be a photographer and see the world, and Dean admits that he wants to be a mechanic. As he talks about how cool it is, Robin kisses him. She asks if he's kissed a lot and Dean insists that he has. Robin doesn't believe him and tells him that he'll have to keep practicing, and kisses him again.
Robin asks where Dean went, and he says that it's a long story. He asks where Timmy is and then says that they have to leave. Robin doesn't see a reason to trust him, and Dean realizes that she remembers him.
Dean and Robin are kissing on the porch and she hesitates. He assures her that he won't leave her and invites her to the school dance.
As Dean tries to get Robin out, the door slams shut. Timmy comes in and says that he can't stop it. Objects start flying through the house as Dean gets Robin to the back door just as Sam comes in. The door locks behind Sam and Dean tosses a box of salt to his brother and tells him to make a circle. Dean then tells Robin to stay in the circle. Timmy comes in and says that he can't control "her," and Sam realizes that he's talking about his mother. Sam asks him to tell them about the fire, and Timmy describes how they were driving home and crashed in the woods. His mother pushed him out but was caught in the flames. Timmy ran through the woods until he found an empty building, He hid there and cried for his mom, and she came. However, he realized that she changed. She was the one who gave him the action figure on his ninth birthday.
Sam realizes that the action figure is the key and asks Timmy for it. The ghost appears and shoves Sam back, and Dean drives it off with an iron poker. He then grabs the action figure from Timmy and burns it on the stove. A wind blows in, breaking the salt line, and they realize that the figure isn't the anchor holding the ghost there: it's Timmy. Sam figures that Timmy's mother is protecting her son from everything, whether it's a threat or not.
Robin panics and tries to run out, and Dean grabs her. The ghost appears, knocking the poker out of his hand, and starts choking him. However, when she realizes that Sam is talking to Timmy, she appears back in the kitchen and starts choking Sam. Dean runs in and the ghost chokes him as well. Sam tells Timmy that he has to try and stop her, and tell her to go away. Dean tells him that his mother is a ghost and she's going crazy because she can't move on. He looks Timmy in the eye and tells him that he has to do what's best for him even if it hurts the ones he loves. After a moment, Timmy gets up and hesitantly tells his mother to stop. Dean tells him to take control and the boy yells at his mother's ghost, telling her to stop hurting people. Timmy promises that he'll be okay but she has to go and never come back. The ghost smiles for a moment and then fades away, and Timmy runs to Dean.
That night, Robin talks to Dean and realizes what his family business is. She assures him that he still looks pretty rocking, and admits that she loves staying in town and owning the restaurant. Dean figures that neither one of them knew everything at 16, and Robin says that she knew one thing. She kisses him and goes into the house with Timmy. Sonny thanks Dean for his help and gives him a hug, and Dean promises to see him around.
As Sonny leaves, Sam wonders how Dean knew that Timmy telling his mother to leave would work. Dean figures that he got lucky, and Sam figures that Dean got lucky to find the farm. When he asks why he left, Dean says that it didn't feel right and he couldn't wait to leave because it wasn't him. As they get in the Impala, Dean looks back at the house.
As Dean prepares for the school dance, Sonny comes in and tells him that John is outside. Sonny tries to explain that it was Dean's big night, but John said that Dean had a job. Dean looks at the photo of himself and Robin together, while Sonny says that the farm gave him a second chance. He offers to fight for him to stay, but John honks the horn outside and Dean looks out. he sees Sam sitting in the car, playing with a toy, and thanks Sonny for everything.
Dean gets in the car and Sam thanks him for always having his back. He admits that it hasn't always been easy, but Dean jokingly says that he doesn't know what his brother is talking about.