I thought the same thing about Bobby's speech. Not only does he seem to make this speech every time he appears, but the man's been lying to Dean about Sam even being alive for a year so really? Dean and Sam both are already calling him all the time to talk about each other? It's just that whole "you have issues" thing--it is total lampshading that brings you out of the story because within this universe the issues they have with each other, like the things people deal with in real life, are not issues, they're stuff going on in your life that's important.

I mean, a friend of mine is always dealing with a couple of family members who are married and have a totally toxic relationship that they try to drag everyone into and is hopeless. But Sam and Dean aren't a couple at each other's throats. Their issues are supposed to be tied to actual life and death things. So it's kind of like...enough already, and if Bobby keeps complaining about it it's going to be his own whininess that needs to get lampshaded. It's not powerful when Bobby's always yelling at somebody this way.