Bobby is at the end of his very long and rugged rope again. To be fair, with the pleasure of sharing heaven with his admittedly favorite nephew, of course, comes with extra baggage. In Dean's case, the baggage is in the shape of an angel. Bobby was pretty sure that both Dean and Castiel got their happy ending together. But in moments like this, he is not so sure. One thing he has to give to the two idjits is that there's not a dull moment since the angel stumbles off their lodge's roof, the old-fashioned way. Though this time, neither Bobby nor Dean were alarmed. They just shrugged and Dean went and opened the door. Straight into the arms of said angel. Bobby is nobody's fool. He knew of Castiel's attraction to Dean before the idjit himself noticed. Typical Dean, never expecting anything good for himself. This leads to Bobby sitting on his well-deserved rocking chair in his well-earned heaven, and making his confession to a cosmic teenager god out of desperation.
"Jack, or whatever the proper title I should have addressed you with, please let them stop fighting. This is Heaven, for fuck's sake. Or did you break it already? Ok, ok, I'm sorry." Bobby wipes his brow, "All I'm saying is, this can't be it for Dean. He is still, well, him. Which is good. And bad if he can't even accept himself and his feathered friend, here."
"Now, I ain't no saint. I have held hands with a couple o' fellas back in my days and I can't say I have any regrets in that regard. Maybe I should've given Dean the talk?! … " He takes a swig from his bottle, "Nah, if that could help, I would've done it a long time ago."
"Dean is a great kid. But things just happen to him. I remember one time when he was 15, he came to me alone, without John. Hitchhiked to my place. And you could tell something happened to him." Bobby wipes his face with his rough hand. "His face was a purple bruise, his lips were busted." Bobby breathes, "And, the worst part was, he wouldn't let me patch him up, he said he deserved it. A 15-year-old kid! He didn't say anything, but he didn't have to. I knew it was John. Probably after too many drinks." Bobby sighs, "I hated John for that."
"God, Jack, if you are God, you probably knew all this already, and I probably should just leave the lovebirds alone. But if Dean kicks out Cass again for wanting to build him a cowboy-themed heaven, I will whoop Dean's ass myself! What idjit doesn't want a cowboy-themed heaven?! Well, Amen."