I know what you mean about the angst; realizing he'd pushed Sam into something he wasn't comfortable with would hit Dean so hard. While Sam would keep more perspective, and be a bit, "Why didn't you say something if you didn't like it?" (In my mind, the only scenarios where one of them would express discomfort, and the other one wouldn't completely back off right away, involve demonic possession.)

I just can't get my mind past Dean's whole, "I can't risk hurting my brother like that." Which is probably good.

Screwed-upness is fun.