Various things I noticed during the ep, in no particular order:
At the beginning of this episode, Dean has already had enough, and more than enough, and they just keep asking for more.
Castiel pretty much came right out and said that he fell for Dean. Probably not at all in a sexual way, because Cas probably understands lust in the same way that humans understand string theory. He's aware of its existence, he knows it's probably important, but damned if he could tell you how it works. Still, he's clearly fascinated, and by the end of the episode he's even taking on Dean's speech patterns. "He was workin' against us."
Do we believe what Alistair says about John holding out for a hundred years? Because if we take his version of events as fact, then we must also believe the demons were willing to trade John, their righteous man, for Dean in "Crossroad Blues" and wait another ten years (thousands of hell-years) before they got their paws on his soul.
There was a guy in there with Alistair. There was a mortal in there, probably one with a family, and when the demon burned out of him, it left the hideously abused body of somebody's husband or brother or favorite uncle. I doubt that the poor guy had a snowball's chance in hell of surviving possession by Alistair no matter what, but I still wonder what his family is going to make of his death. Dean carved him up like that, and he did it because someone told him to.
Dean's eyes went dark, nearly black, when he said Cas wouldn't like what walked back out. Nice touch, Show.
Sam says "He can't do it," and Ruby jumps right in with "You don't want him torturing people again." How does she know that Dean broke in the first place? Maybe she assumed, but that rock solid certainty? Did Sam tell Ruby Dean's darkest, most soul-crushing secret?
Ruby witchcraft in action. Have we seen that before? And it's interesting how petulant she gets at the suggestion that Sam doesn't want/isn't dependent on her.
"This is the last thing I want." Obviously it isn't, Sam.
She called him SAMMY?! And he let her?
That's not erotic and vampiresque at all. Evil!Ruby face!
"Do you really think this is going to fix you?"
Anna has old favors to call in? How? Didn't she piss off the whole of heaven when she fell?
Anna's "together we can..." speech sounded like a temptation, a seduction. Offering knowledge of good and evil. Maybe next episode she could munch on an apple while she says shit like that.
Sam doesn't just ask for a miracle - he demands it. Damn.
I was rather pleased to see Castiel get pissed with Uriel for setting his human up like that.
And the last scene, with Castiel at Dean's bedside. Jensen Ackles, I take my hat off to you. That was amazing, heartbreaking work, dude. (Will someone give the man an award already?) As for Dean, I really hope this is rock bottom for him, and that from here on we get to watch him claw his way back up. I sympathize with his despair and his "Find someone else," because he's just taken an intense physical and psychological beating. But come on, soldier. Stand up.