the conversations bobby has with sam and dean in the car in 07x09 that seem to function as sort of pre-07x10 goodbye where he’s being given a supposedly meaningful individual last scene with each of them are so funny because they are both. pretty callous moments that are meant to be taken in support of bobby functioning as their father figure. but i also think they’re somewhat interesting in comparison to each other & their general relationships with bobby. sam’s scene with him is almost entirely about dean and bobby questions his ability to properly worry about dean & be there for him if something actually was wrong (‘aren't you full up just playing snuffleupagus with the devil all the livelong?’). and he doesn’t provide any sort of meaningful response when sam expresses the (very arguable) belief that ‘a lot of people got it worse’ than he does. his conversation with dean is slightly more considerate, but he also tells him to let go of his personhood as a form of self-preservation in the face of growing nihilism (‘that ain't person behavior, son. you're a hunter, meaning you're whatever the job you're doing today.’). i think these are both fairly representative of the whole of bobby’s individual relationship to them — sam and bobby’s relationship is often determined by sam’s proximity to dean (or the way that dean views sam at that moment), and dean and bobby’s relationship is based on dean’s attachment to hunting (also seen in bobby and dean (according to the 05x22 narration) not really seeing each other in-between seasons five and six)
