On one hand I can appreciate the slashiness of the Dean/Castiel setup, that has Dean so committed to Castiel loosing his virginity, and makes it nearly impossible not to think that after the prostitute didn't work out, Dean would help out Castiel with a buddy fuck. OTOH that whorehouse scene made me cringe. And I'm not even talking about the gender politics of the show or anything (though not doing so great there, though it could have been worse, and why would father issues make someone become a sex worker anyway? I don't even get the pop psychology here). That scene also hit my embarrassment squick, because it wasn't cute awkward, but cringe-worthy awkward.
Another thing that threw me was the sequence of events as Dean and Castiel contacted Raphael. First they are in some kind of hospital (?) where the host is, and do the oil ring thing, and Castiel calls the archangel. And then they drive to some house to meet him again? Is my copy missing something? Watching that cut again it seems to be that they waited in vain in hospital for some time, and then Raphael transported his vessel to the place Dean and Castiel are staying at? But this was confusing.
Otherwise I felt bad for Sam a lot, even though it's of course not surprising that Lucifer wants him. Also I like how Lucifer seems really quite the sympathetic character compared to the rest of the angelic bunch.