Ok, I guess since it's still within the first 24 hours of airing, I'll put stuff behind a cut, just in case there are people on my flist who haven't watched the episode yet:
A couple of delayed reactions:
1. Wait a sec...I've never been in a long term committed relationship either, and I'm only 2 years younger than Dean! There's nothing wrong with that!
2. Hey, no wonder Dean is always complaining about how tired he is...it's not Hunting, it's the fact that the dude NEVER SLEEPS. Seriously, I mean, I'm all for the show making their lives horrible, but at least make it believable. No one could be so sleep deprived, and drink so much, and look as good as Dean Winchester.
Was Dean hallucinating that therapist from the beginning? Or just during their last conversation when she looked a lot like Meg? Because if she was a figment of his imagination from the beginning, then Dean totally diagnosed his own psychosis and then gave himself a pity party.
I've got to download the episode now so that I can time-line it. I don't think they slipped up and put any dates in there though, sadly. So far Season 5 has been the absolute hardest to time-line...S4 was the easiest.