601 - addendeum
So, as mentioned in the previous post, Bobby not telling Dean that Sam was out of Hell, while knowing that what Dean was going through wasn't exactly normal grieving given well, HELL and all, was the lump I couldn't get down.
But destina pointed out it was the "You got out!" that sold it to her.
Not so much to me because how could Bobby think that however out of hunting Dean may be, he was in anything but a type of hell on earth knowing Sam was in torment? He knows how co-dependent the Winchester boys are.
And then I thought...
What if that's part of the "out"? Not only out of hunting but out of a co-dependent relationship that Bobby thought could only bring more pain. I mean, he's not stupid and he's not blind and he has to have seen the clues that said the boys were closer to each other than was healthy. He didn't like it but he didn't say anything about it because he couldn't take away the only thing they had but now, Dean has more. And Sam is... changed. What better time to let them grow apart?
If Sam had wanted to tell Dean, I suspect Bobby would have tried to talk him out of it.
You can live with your metaphorical heart ripped out, hell, no one knows that better than Bobby. But what kind of life can you live when every breath is tied to your brother's? When every hurt is mulitplied by two? When you've spent a year ripping each other into pieces and yet not been able to step away? And the next time one of them dies, who says the other will survive it?
This way, they're both alive.
And that works even if you don't take it as far as the Wincest.