Dean Winchester and Bobby Singer's relationship consists of that of a friendly working relationship, and Bobby is considered a father-figure to Dean. Like Dean, Bobby is also a hunter. Bobby gives Dean advice to help him personally and on jobs. Bobby's house is like a home to Dean. Dean is also Bobby's favorite.
Background
Bobby is a family friend of the Winchesters and they have known him for a while. Whenever John had a case, he would drop the boys at Bobby's and he taught them how to hunt. Bobby is also a hunter and has stacks of books of lore of anything that is huntable. There was one time when Dean was young that Bobby didn't do what John asked and took Dean to the park to play catch instead of practicing with rifles.
Season 1
| “ | No. But I know it's something big. Storm is coming, and you boys and your Daddy you are smack in the middle of it. | ” |
— Bobby Singer
in Devil's Trap | ||
Dean goes to Bobby's with Sam in Devil's Trap, when John gets captured by Meg. Dean recounts what happened to Bobby and asks him for assistance. So Bobby shows Dean and Sam some lore, until Meg shows up. While Dean is excersing Meg, Bobby pulls Dean to the side and tells Dean that there really is a human girl trapped inside, and getting rid of the demon may kill her. Dean continues on with the excerism anyways. After Meg dies, Bobby tells Dean to go get their father and he'll deal with the cops. Dean is concerned that Bobby may have trouble, but Bobby rebuts by saying do you think you invented lying to the cops? Bobby also tells Dean to bring John by, and promises not to shot him with buck shot.
Season 2
Bobby, Sam, and Dean in Tall Tales
After John's death, Dean spends his time fixing up the Impala at Bobby's place. Dean stays there until Sam brings him a job.
Dean doesn't see Bobby for a while until Sam get possessed by Meg in Born Under A Bad Sign. He and Bobby team up to free Sam the Demon. When Dean attempts to exercise the demon Bobby notices the demon put a brand on Sam's arm to lock the demon inside Sam. Dean thanks Bobby and Bobby gives Dean advice not to talk about the hunter Sam killed while possessed.
Bobby comes to help Dean again in Tall Tales, when they find a bunch of strange murders Dean can't make sense of. Not to mention Sam and Dean are fighting. It is Bobby who tells them they are dealing with a trickster and they all go hunting. Once they kill the Trickster, Dean thanks Bobby for his help and Bobby responds by saying it alright but they need to get out of town.
When Sam goes missing Dean calls Bobby. Bobby comes right away and meets Dean. They head to the roadhouse only to find it burnt down to the ground. Then Dean gets a vision of Sam in a town. Bobby is concerned when this happens to Dean. Bobby asks Dean if Dean's vision is like Sam's? Dean tells Bobby no and they figure out where Sam is, Cold Oak. They arrive near town (the road is blocked) and walk in looking for Sam. They find Sam, only to watch him get stabbed.
A week after Sam's death, Bobby asks Dean if he wants to bury Sam. Dean snaps at Bobby and tells him to leave. Bobby tells Dean the world may end, and Dean responds, "Then let is end!" Bobby tells Dean he doesn't really mean that, but Dean begs to differ. Bobby leaves Dean telling Dean he knows where to find Bobby. Dean later comes to Bobby's door, with a resurrected Sam. Bobby confronts Dean and yells at him for being so stupid. Dean tells Bobby he did make a deal, and it doesn't matter since John made a deal for Dean. This way, something good comes out, Dean tells Bobby. Bobby asks 'How’s your brother going to feel when he knows your going to hell?" Dean asks Bobby not to tell Sam. Because Bobby cares for Dean, he does that.
Then they head to the Devil's gate for one final showdown with Yellow Eyes. The gates does get open and lets some demons out. Bobby tells Dean,"I hope you boys are ready, because the war has just begun." Dean responds by saying, "We got work to do."
Season 3
| “ | This isn't your fight." "The hell it isn't! Family don't end with blood, boy. | ” |
— Dean and Bobby
in No Rest For The Wicked | ||
Bobby joins Dean in a hunt where they are dealing with the seven deadly sins. Dean jokes with Bobby when Bobby is wearing a suit when they are investigating. While waiting for the guy they believe responsible, Bobby tells the boys they can't just walk in there without a plan. After an incident, Bobby figures out they are dealing with the Seven Deadly Sins.
Bobby continues to help from the sidelines. Like telling Dean how to destroy the cursed Rabbit Food in Bad Day at Black Rock.
Then in Dream A Little Of Me, Dean gets a call from the hospital about Bobby (Dean was put down as Bobby's emergency contact). Bobby is in a coma and the doctors don't know what to do. So Dean checks Bobby's last job to see what happened to him. When they don't know what to do, they decide to ask Bobby. This means dream walking in Bobby's head. Dean finds Bobby and tries to convince Bobby this is a dream, but Bobby is too frighten to think straight. Dean also tells Bobby that Bobby is like a father to him. Dean meets Bobby's wife who he killed (when she was demon possessed). Bobby does believe Dean and wakes up. Later Dean asks Bobby about his wife. Bobby answers they all get into hunting somehow; Bobby's wife was his.
As Dean's final hours are counting down, Bobby finds a way to locate Lilith. They find her and Sam suggests to summon Ruby. Bobby tries to talk Dean into agreeing with Sam, but Dean refuses. Bobby leaves to go find another way. As the boys are trying to leave, the car won't start and Bobby reveals he taken a part out. Bobby tells Dean they aren't leaving him behind. Bobby also continues by asking Dean how many hallucinations hes had. Dean is surprised and asks how Bobby knows. Bobby respond by saying I know what its like to have hellhounds on your butt. Bobby finishes by saying he gonna follow.
On the way there, Dean kills a demon, because now Dean can see them. Bobby tells Dean he can see them now most likely because Dean's almost hell's bitch. Bobby suggests to use this to see where Lilith has all her demons stashed throughout the neighborhood (which she does). Bobby turns the sprinkler system into holy water to protect the boys as they go into the house. Bobby watches the clock as times ticks away for Dean. He mumbles under his breath for Dean to hurry up.
Season 4
Bobby re-unites with Dean.
When Dean comes back from hell, he calls Bobby, but Bobby hangs up on him. So Dean heads out to Bobby's house. Bobby is shocked to see Dean on his front door. Dean says hi, but Bobby attacks Dean thinking hes a shapeshifter. But Dean proves hes not by cutting himself with a sliver knife. Bobby almost believes Dean, but slashes Dean with holy water just to make sure. Bobby is very glad to see Dean alive again. Dean notices a bunch of empty bottles in Bobby's study, and remarks about it. Bobby tells Dean it was how Bobby dealt with Dean's death. Later, Bobby and Dean go after Castiel together.
After meeting Castiel, Dean doesn't want to believe Castiel is an angel. Bobby tells Dean there is a possibility and shows him lore. Then the rising of the witnesses comes, Bobby figures it out to be the signs of the apocalypse. Bobby also shows Dean his panic room, which Dean loves and tells Bobby "Your Awesome".
{C In When the Levee Breaks, Bobby helps Dean lock up Sam so he can detox on demon blood. Dean asks Bobby how long he thinks this will go on. Bobby replies, "Here, let me look it up in my demon detox manual. Oh wait - no one ever wrote one." Dean is silent and Bobby continues by saying he doesn't even know if Sam will live through it. After Rufus's call, Bobby informs Dean that seals are breaking fast. Bobby also asks if this is the right time to deal with Sam's demon blood problem? Bobby suggests to use Sam in the coming Apocalypse, but Dean doesn't like this idea. Bobby tells Dean, he doesn't like it either, but Sam could be helping instead of being locked up here.
Bobby gets angry with Dean when Dean agrees to be the angel's "bitch" (mostly because after all that fighting that, Dean gives in). Though Bobby sees Dean's point when Dean says its either the angels or Sam trusting a demon. Then they notice its gone quiet downstairs, they watch Sam get flinged around the room. Bobby and Dean grab him and tie Sam to the bed. This pains Dean to do this and Bobby knows how Dean feels, but keeps it together. Back upstairs Bobby asks Dean again if they're doing the right thing. Dean answers that they saw what the blood was doing to Sam; it's killing him. Bobby resorts, no its not, we are. Dean is surprised at this.
Bobby tells Dean he can't keep quiet any more. Bobby tells Dean that they're killing Sam by keeping him down there. If they don't get Sam what he needs, he won't last much longer. Dean refuses and Bobby replies that Sam will die. Dean shouts back, at least he dies human. Dean continues on how he would die for Sam, but he won't let Sam drink demon blood. He tells Bobby, hes found his line.
After the fight with Sam, Dean returns back to Bobby's. There Bobby asks if Dean is gonna call Sam. Dean tells him no, because Armageddon is just around the corner. Bobby continues on by saying even though Sam has messed up, hes your brother, but Dean cuts Bobby off. Dean is still very hurt by Sam's betrayal and Bobby is trying to help Dean patch it up. When Dean refuses to, Bobby get angry and says, "Well boo-hoo, I am so sorry your feelings are hurt, princess! Are you under the impression that family’s supposed to make you feel good? Make you an apple pie, maybe? They’re supposed to make you miserable, that’s why they’re family!" Dean resorts it was Sam's choice and Bobby counters that Dean sound like John. Bobby tells Dean John had rathered push Sam away then to reach out to Sam. Bobby finishes with telling Dean, not to be his father. Dean is shocked by Bobby's words, but they do move him towards fixing his relationship with Sam.
Season 5
Posessed Bobby holding Dean
| “ | That's the round I mean to put through my skull. Every morning, I look at it, and I think.. "Maybe today's the day I flip the lights out." But I don't do it. I never do it. You know why? Because I promised you I wouldn't give up! | ” |
— Bobby Singer
in Point of No Return | ||
Bobby brings Dean's beloved Impala to their motel and helps Dean with the research on the Michael sword. Just when Dean figures out where it is, Meg walks in with two other demons and "Bobby" attacks Dean. Bobby is possessed. Meg orders "Bobby" to kill Dean, but Bobby manages to regain control of his body and stabs himself with Ruby's knife (its because he cared for Dean so much that he is able to overpower the demon). Although during this attack, Meg refers to Bobby as Dean's daddy.
Later in the hospital, Bobby is told he will never be able to walk again. Dean tells Bobby that he would be up kicking butt in no time. Dean tells Bobby, screw everything - demons - angels - the whole damn apocalypse. They need to talk everything on and kill the devil. Later on, Dean watches Bobby from the doorway and notices Bobby's depression. Dean doesn't like to see Bobby depressed.
Then in The Curious Case of Dean Winchester, Bobby comes in on a case that involves a poker game where you can either gain or lose years. When Dean finds Bobby and hears that he played the game, Dean gets angry. But Dean still does play the game and gives Bobby 25 of his years. Dean loses and lives the joys of old age. Not to mention that Dean and Bobby bicker like an old married couple. When Dean returns back to normal, he tells Bobby he doesn't Bobby as useless and hes glad Bobby is around. Bobby is touched by this and when Dean leaves Bobby visibly shows that he is thankful for Dean's words.
In Dead Men Don't Wear Plaid, Bobby's dead wife is brought back from the dead. Dean is suspicious of this and warns Bobby. But Bobby strongly believes it won't happen to his wife. Dean asks what would Bobby do if he was in their situation. Bobby said the exact same thing, but pulls a gun on Dean and tells him to get out. Dean still hangs around Bobby's out of concern for him. When the zombies attack, Dean fight along side Bobby. Whens it over, Bobby reveals a message Death left behind for him. This happened because of his support to Sam and Dean.
Then Dean decides to say Yes to Michael (Point of No Return), and they lock him Bobby's house. Bobby and Sam look for other ways to ice the devil, but Dean keeps making comments. Bobby says something and calls Dean son. Dean resorts, your not my father. Bobby is visibly hurt by this comment. All is forgiven when Dean doesn't say no.
Though Dean gets angry with Bobby when Bobby "lends" his soul to Crowley to find Death's location. Bobby resorts its just one soul, but Dean doesn't care. The fact was Bobby still sold his soul. They split up to do different tasks (deans goes after death, Bobby to stop the virus). When everything is ready, Bobby tells Dean he thinks Sam can really do it. Dean also shows Bobby how the rings work. Bobby comes along when they bring Sam to Lucifer. Bobby also backs Dean up when Dean goes to have a talk with Sam.
Season 6
Dean calls Bobby
Bobby and Dean meet again when djinn Dean. He brings Ben and Lisa to Bobby's so they can be safe. Though Dean gets angry with Bobby when he finds out Bobby knew Sam was alive and didn't tell him. Bobby responds by telling Dean, he didn't tell Dean because Dean go out of this life, and didn't want to drag Dean back in. Dean was able to get a normal life that most hunters could never achieve. Dean later returns to Bobby's to pick up Lisa and Ben.
In Weekend At Bobby's, Dean calls Bobby with his concerns about Sam. He tells Bobby hes the only person he can talk to about this stuff. When Bobby tells Dean he doesn't have time for this, Dean calls Bobby selfish. Bobby tells Dean to bring Sam in. Dean brings Sam and Bobby says:
| “ | Sam, Dean, I love you like my own. I do. But sometimes...sometimes you two are the whiniest, most self absorbed, sons of bitches I ever met. I'm selfish? Me? I do everything for you. Everything! You need some lore scrounged up. You need your asses pulled out of the fire. You need someone to bitch to about each other. You call me and I come through. Every! Damn! Time! And what do I get for it? Jack with a side of squat! | ” |
— Bobby
in Weekend At Bobby's | ||
Dean responds by saying Bobby, if you need anything, just ask. Which they do. Sam and Dean fly to Scotland to dig up Crowley's bones for Bobby. After thats done with, Bobby apologies to Dean for what he said earlier. Dean tells Bobby, he was right when he said they take advantage of him. Bobby cuts the moment off before it gets too emotional.
InAppointment In Samarra, Dean leaves Bobby to watch over Sam, while he does his wager with death. Bobby thinks what Dean's doing is stupid, but agrees to watch Sam. When he returns, Dean arrives just in time to save Bobby from Sam. Dean tells Bobby that he can't keep doing this. They can't lock up Sam every time he tries to kill someone. But lucky for Dean, Death gets Sam's soul.
Bobby helps Dean wait for Sam to wake up, and offers him a drink. When Sam does wake up and tells Dean he doesn't remember anything other than jumping in the hole. As Sam is getting his rest, Bobby tells Dean he can't exactly be friendly with Sam, because about 10 days ago, Sam tried to kill him. Dean doesn't see it this way and responds that it wasn't really Sam. Dean continues on by saying they can't tell Sam this cause it might damage the wall in Sam's head. Bobby tells Dean that Sam won't like the fact that Dean is lying to him. Dean resorts well Sam doesn't need to know.
In ...And Then There Were None, Bobby stands up for Dean and Sam against Samuel. Bobby yells at Samuel for selling his own blood out. Samuel resorts by saying Bobby is the man pretending to be Sam and Dean's father. Following that in My Heart Will Go On Dean is worried how Bobby is reacting to Rufus's death. Dean racks his brain on how to cheer Bobby up. In Mommy Dearest, Bobby gives Dean naming rights of Eve's latest creation.
In The Man Who Would Be King, Bobby tells Dean Castiel could be working with Crowley. Dean disagrees with this thought. But when Castiel slips up, Bobby and Dean work together to trap Castiel.
In The Man Who Knew Too Much, Bobby helped Dean deal with Sam's state, despite feeling helpless as well. Later Bobby convinces Dean to come with him to go after Castiel. Dean hesitates, but Bobby remind Dean this is what Castiel wanted. Dean agrees and goes with Bobby. Before they head in, they scope out the place, but then notice a horde of demon coming at them. They get into the Impala, which is slammed into and wrecked the Impala. When they come to, Dean checks if Bobby is alright. Then they go in together to stop Castiel.
Season 7
| “ | "Course, if at any time you want to decide that's utter horse crap, I'll be where I always am. Right here." "What? Do you want to do couples yoga or get back to hunting the Big Bads?" "Shut up. Idgit." | ” |
— Bobby and Dean
in Hello, Cruel World | ||
Soon after Castiel claims hes god, he leaves. So Bobby and Dean head back to Bobby's house. Dean begins to start fixing the Impala. In Hello, Cruel World, Bobby is worried about Dean due to Dean losing Castiel and Sam possibly going off the edge. He asks Dean how he is doing. Dean tells Bobby that hes fine, Bobby doesn't believe this and tells Dean that when he does want to talk, hes going to be where he always is.
Later on when Dean discovers Bobby's house burnt down and believes Bobby to be dead. He call Bobby in a similar fashion as he did to John in Home, and admits that hes not okay. Although, Dean is relived to see Bobby alive in The Girl Next Door. Bobby helps him and Sam escape from the hospital. They hide out in an abandoned home, while Dean recovers. Dean and Bobby also really get into a Spanish soap opera.
Dean looks to Bobby for support with Sam's situation, and Bobby reassures Dean that Sam will be fine. Bobby is worried about Dean though. When guilty people are being put on trail by Osiris, Bobby tells Sam to get Dean out of there.
In How to Win Friends and Influence Monsters, Bobby gets more worried about Dean when Dean begins to complain about the job and how he wants to be people. Bobby quickly points out that people don't sit in a van full of guns and an old man. Bobby also points how Dean tried to be normal with Lisa but it didn't work. Bobby tells Dean that he seen men who talked like Dean dead and quickly tells Dean to find something to live for. Later on Bobby is grabbed by the Leviathans, and Dean and Sam rush to save him.
Following the events of the previous episode, Bobby is shot by Dick Roman and Dean is extremely concerned for Bobby's life. He rushes Bobby to a hospital and watches as Bobby is being tended to. When a man approaches Dean about donating Bobby's organs, Dean gets extremely angry and punches the wall beside the man, and tells him to walk away. Dean doesn't want to think of the possibility that Bobby might die. Dean is happy to see Bobby wake up, but is devastated when Bobby flatlines. Dean watches in horror as the nurses and doctor work to save Bobby's life.
In Adventures in Babysitting, Dean is taking Bobby's passing hard. He spends weeks drinking and brooding around the house he and Sam are staying at. Dean begins his hunt for Dick Roman to get his revenge. Dean is also unwilling to tell people that Bobby has passed on, showing that Bobby's death really affected him. In The Slice Girls, its revealed that Dean kept Bobby's flask and was using it as well as using to remember Bobby. Dean even calls a one night stand up to get it back.
Dean has a sinking feeling though that Bobby might be still around. In Party On, Garth, the sword that fell out of Dean's hands came to Dean again which makes Dean believe that Bobby might be still around. Garth even tells Dean that EMF was coming off the flask. Dean desperately wants to believe Bobby is around, but Sam tells Dean that Bobby would have created a sign. Unknown to Dean, Bobby is watching, but unseen to the eye.
Upon learning new tricks, Bobby eventually reveals his existence to Dean, who is shocked. Later on Bobby becomes visible to Dean, Dean is stunned to see Bobby. Dean asks Bobby what he was thinking when he decided to become a ghost. Bobby is hurt that Dean said this, and vanishes. Dean is unsure of what to do, and throws Bobby's flask into the trunk of the car. Dean mentions to Sam that Bobby is messing up the natural order and its not going to end well. Bobby is sitting in the back, silently listening to all this.
Dean becomes worried though that Bobby is slowly becoming one of the ghosts that they hunt. Although Bobby is not concerned about it. Dean first notices this when Bobby sneaks his flask in Charlie's bag to go into the head office of Dick Roman. The ending result is that Bobby lays down some serious ghost mojo and breaks Charlie's arm. Dean gets further proof in There Will Be Blood, when Bobby loses control and breaks a mirror when discussing creating the weapon to kill Dick Roman. Dean is slowly becoming worried about Bobby, this causes his to lock Bobby's flask in the safe in order to keep Bobby's ghost rage in check.
In Survival of the Fittest, Sam deals with the possessing Bobby knowing Dean wouldn't be able to. Bobby disappears for a bit and returns to them in Rufus's Cabin. Dean asks Bobby what it was like being a ghost and Bobby tells him that its like itch you can't scratch no matter what. This saddens Dean, and Bobby tells them to burn his flask. As they prepare to send Bobby off, Bobby says one final goodbye to the boys. Bobby disapates with a smile and Dean is forced to say goodbye for a second time.
Season 8
In Taxi Driver, when Dean hears about Bobby is in hell, he and Sam decide that they need to rescue Bobby. Dean tries to go with Sam, but Sam insists on doing the trial alone. When Sam returns, and releases Bobby's spirit, Dean is worried for Bobby's soul with Crowley shows up. Luckily Naomi shows up and Dean watches Bobby's soul go to heaven.