What major conflicts are there between Bobby and one or both of the Winchesters? He mostly seems to go bitchly along with one or the other in their conflicts. That’s why his gruff persona seems more cutesy than believable. It’s telling that his beef with the two of them in Weekend at Bobby’s is simply that they take him for granted and he has his own life. His role, generally, is to be a sounding board, provide a home base, provide them with information when they need it, and save them when they need it. He might as well not be a character.
I guess looking at it from a Watsonian perspective, this is kind of interesting: Bobby has self-worth issues, I guess, needing Sam and Dean’s support, or wanting it, more than anything else. He's also not their father. He claims the role because he wants it, because he wants to prove he can parent adequately, but in fact he doesn't parent them, and there's no evidence that he ever did. The one story we know is that he played baseball with Dean, and this pissed John off. This probably did make Bobby feel like he was better with the kids than John was, but it's not much for evidence of fatherhood.
From the Winchesters brother's perspective: Dean used Bobby as an alternate father to assist him in his rebellion against John after John’s death, kind of an emotional support and quasi-replacement, I think. I'm not entirely sure about Sam: I think he mostly went along with the father thing because Bobby and Dean said it (and he does love Bobby).
The one time Dean does reject Bobby as a father, in Point of No Return, Bobby comes down hard on him. "That’s the round that I mean to put through my skull. Every morning, I look at it. 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!"
Note what Bobby doesn't do: Offer any evidence of his fatherhood to Dean. No reminders of how he was there for Dean growing up (he wasn't). No assertions of authority. Bobby Singer did not raise the Winchesters brothers.
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