‘Bobby says what any normal person would in this situation, which makes it easy to overlook just how unusual this is, because actually, this isn’t normal for Bobby Singer. This isn’t how he relates. Bobby is the man who greets genuine anguish with a terse “boo hoo” or “suck it up”, and when Sam chose a demon over his brother, he told Dean “so sorry your feelings got hurt, princess”. Later on in this very season, he will tell Dean to shove his grief down so deep until essentially he can’t find it anymore. I mean, it’s not just that Bobby isn’t touchy-feely; it’s that he actively derides and discourages displays of emotion in his adopted sons.
So that a man who has time and again told Dean to deny his pain now is not only acknowledgingthat pain, but validating it, should show that the circumstances here are so extraordinary even Bobby can’t deny them any longer.
So why now? Why does Bobby offer to talk now, and about this, especially when Team Free Will has hunted world-threatening monsters and Sam’s gone off-the-rails before?
The only difference here is Cas – it is the loss of Cas that has Bobby reaching out in a way so foreign to him it visibly freaks him out as he does it.
I think the root of this action, as with many things in this series, is John Winchester. In season 4, especially, it’s made very clear that Bobby has no love for John, and that he blames John for a lot of the emotional and mental dysfunction that his two sons currently struggle with. In “Lucifer Rising”, he even snaps when he thinks Dean sounds too much like John, saying “you’re a better man than your daddy ever was”.
Bobby also knows that it was losing the love of his life that pushed John over the edge, and turned him from a normal man into a cold-blooded, obsessed monster. Maybe he understands this even more than Dean and Sam do, since Bobby lost his wife to a demon too.
Look, Bobby ain’t no idjit. There’s an obvious parallel here, between John losing Mary and Dean losing Cas, and Bobby can see it. And given how much he dislikes John, it only makes sense that if Bobby sees Dean on the path to becoming like his father, he’s going to do anything he can – include offering to talk about Dean’s feelings – to stop it.
What I’m saying, in other words, is that this one bit of dialogue reveals that Bobby thinks Cas is the love of Dean’s life, and that he’s afraid losing him will turn Dean into the next John.
And like I said, Bobby ain’t no idjit. Given how broken Dean becomes in this season, he wasn’t exactly all that wrong.’
