Dean and Bobby

Dean Winchester and Bobby Singer have friendly working relationship. Like Dean, Bobby is also a hunter. Not to mention Bobby being like a father to Dean. 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 favourite.

Background
Bobby is a family friend of the Winchesters and they have known him for a while. Bobby is also a hunter and has stacks of books of lore of anything that is huntable. Dean does trust Bobby though, and goes to him when they need help. Although Bobby isn't seen a lot early in Dean's life, he is talked about.

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

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
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 possesed by Meg in Born Under A Bad Sign. He and Bobby team up to free Sam the Demon. When Dean attempts to excercise 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 posessed.

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 fightning. It is Bobby who tells them they are dealing with a trickester and they all go hunting. Once they kill the Trickester, 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 repsonds, "Then let is end!" Bobby tells Dean he doens'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 resurected 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 repsonds 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

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 emergeny 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 dreamwalking 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 posessed). 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 neighbourhood (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
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.

Season 5
"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