Uhm, not really sure. I have to re-watch it again some time to get it. I just came home.. LOL

Yes, I think it's a little bit of building it up more. *sighs* Makes this ep all that much sadder when you think about it.

Yes, well we have seen that angels aren't really that sensitive when it comes to talking to humans, so I kind of get that. He just sees Dean's insecurities as inconvenient and wants to get rid of them. There is no use for them to him.
I think Dean has a reason, too but then again maybe he needed that as well... *shrugs*