9.08, Rock and a Hard Place.
My main takeaway from the actual hunt part of this episode is that Virginity Is A Bullshit Construct and Jody's the only one with a healthy mindset on that fact. :P
TAMMY [approaching SAM] Her favorite? She has no idea what kind of girl Honor is.
SAM You don't say. Uh, Tammy, right? The poet?
TAMMY Mm-hmm.
SAM Tammy, why -- why don't, um, why don't you tell me what kind of girl Honor is?
[...]
TAMMY Honor is going to hell.
I love that line... because heck what an on-the-nose name for a girl who broke her chastity vow, right?
I remember all the "they're using the wrong tools for the job" meta from this episode, because everyone's struggling to cope without actually effective tools, and a startling lack of information on what's actually attacking them. A woman needs light but instead uses a taser that puts a tiny amount of light out. They have no water in their prison cell, and resorts to drinking her own blood in desperation. Dean asks for a screwdriver to try to free them, and all they have to give him is scissors from the first aid kid. But hey, it works, and it's the first PRODUCTIVE use of a "wrong tool," even if Sam and Jody have already killed Vesta by the time he breaks free.
But Dean... when he realizes his phone has been taken, he tears into the lining of his jacket and actually produces a functioning "spare" phone. He's incredibly well prepared for anything... Meanwhile the other people in the cell are beginning to turn on each other-- the other man literally trying to choose who to sacrifice next:
NEIL Okay, look, whatever that fireball thing was, it's taking the weakest, and I am not gonna be next. So, the way I see it, her leg's busted anyway. [NEIL motions to HONOR.] We serve her up. It could buy us some time.
HONOR Screw you, Neil.
[DEAN shoves NEIL to the wall.]
DEAN Busted leg? Try a sprained ankle, okay? Nobody's serving anybody up!
NEIL We are under the gallows, all of us. Give it Honor. It might save the rest of our necks, unless you have a better plan.
DEAN Maybe I do. Maybe we'll give him you. Oh, what, you don't like that idea? Then shut up!
Before dying, Vesta pointed out how messed up Sam was inside, which leads to a massive resurgence of what Dean knows is Sam's lifelong feeling of impurity, his struggle over his own identity, and his fears that he's not even really human anymore... which absolutely breaks Dean, because this is also the first time that Gadreel has taken over Sam specifically to prevent Dean from telling Sam the truth. Dean is just beginning to realize just how helpless he is, and how badly he may have fucked up agreeing to Gadreel's shady terms back in 9.01:
DEAN It's probably the trials, okay? Probably some sort of a, you know, aftereffect. It's not like you're bouncing back from the flu here. I mean, you were glowing with freaking trial juice.
SAM I don't know.
DEAN Well, what else would it be?
SAM Why does it have to be something else? It's always something else. We're always scraping to find some other explanation when maybe it is... just me.
DEAN Oh, come on, Sam.
SAM I'm a mess, Dean. You know it. And sometimes, I feel like maybe I'm never gonna actually be all right.
DEAN You will. All right, 'cause whatever it is, we'll figure it out.
SAM Or this is... just the way I am.
[DEAN closes his eyes in resignation. He shakes his head and goes to sit next to his brother.]
DEAN I can't. I can't let you put this on yourself. Listen to me. It's not you, Sam.
[SAM's eyes glow bright blue and EZEKIEL starts to speak.]
EZEKIEL I wouldn't do that, Dean.
DEAN He deserves to know.
EZEKIEL Your brother is not ready. If he ejects me, he will not make it.
DEAN Damn it, Zeke! How much longer we got to keep playing this?
EZEKIEL Not much longer. I promise you that.
So even though he WANTS DESPERATELY to come clean to Sam, to put everything right again, he knows there's nothing he can do to stop Gadreel, as long as Gadreel has effective possession of Sam's body. He still has to work to keep the peace... Dean really is trapped between a rock and a hard place. He’s dug himself a hole so deep he knows there’s no climbing out, and he’s starting to look for a way to tunnel out of his situation sideways.
Which plan, as we all know, will also go to hell...