Hi! I just wanted to start off by saying that your analyses on the characters are awesome and they really helped further my understanding of the show, so keep up the good work! :D

I was wondering, if you don't mind answering, what did you think of about Dean giving permission for Gadreel/Ezekiel to possess Sam in season 9?

I'm still a bit on the fence about how to feel about it and I thought your particular brand of wisdom might be able to help me out.

Dean had just a few pieces of information at the hospital in 9.01.

These are the details Dean has prior to Sam falling into a coma. He believes that his brother wanted to commit suicide, but that he did change his mind and decide he wants to live.

Two other notable details:

First, Gadreel earns Dean's trust quickly by risking his ass to help Dean, and then on the phone (after being given the fake name "Ezekiel") Cas, relieved and pleased, vouches for Ezekiel. So Dean has no reason to suspect anything nefarious (and in fact, at this point, Gadreel doesn't have particularly nefarious intentions besides staying in hiding away from other angels).

Second, Dean is not the one who pleads with Sam to live in the dream sequence, getting him to say "Yes". It can't be Dean, because 1) "Dean's" face morphs into Gadreels which is clearly intended to indicate to us that this wasn't Dean speaking 2) If Gadreel was somehow projecting the real Dean into the conversation to give that speech, then Gadreel wouldn't be the one receiving the consent. It would truly be Dean receiving it and not just Gadreel pretending. Those words HAVE to come from Gadreel's mouth for the possession to work—not Dean's. We've seen angels morph into loved ones and mimic their voices perfectly several times.

With all that in mind:

After Gadreel pitches his plan to possess Sam, Dean immediately says it isn't his call to make—it's Sam's. It's after Gadreel shows him Sam falling back into the same suicidality from 8.23—wanting to die so that "no one else can get hurt because of me"—that Dean wavers. Still—at the end of the day, whether Sam agrees to live or not was never Dean's choice, and this is something I often see people get mixed up about. Dean doesn't get to choose whether Sam dies or not. It is still Sam who chooses to live. Sam does this by saying "Yes" to Gadreel. This could not have happened if Sam hadn't changed his mind about living. He doesn't know he's going to be possessed, but he has once again beaten back his suicidality and chosen to live. Sam still had hope in a good future.

Sam chose to live. He did not know he was going to be possessed. That's the issue. However, Dean did not intend to keep Gadreel's possession from Sam after it happened. Dean and Gadreel have this conversation upon leaving the hospital:

This conversation suggests that Dean's initial thought process was "We perform supernatural life-saving surgery". He just wanted to get Sam to a point where he'd wake up and they could talk. Like any situation with a relative in a coma, that person in a coma can't consent to surgery. The next of kin is the one who gives consent, because their loved one can't. They can only consent to a procedure if awake to do so. So Dean doesn't stop Gadreel from performing life saving surgery, but his intial belief and intent is that they'll put all of this back in Sam's hands when he's awake.

Up to this point, I don't actually have a problem with what Dean's done based on his knowledge. It's here at the end of the episode, where Gadreel convinces Dean to depart from his intial intent and stall, that in my opinion, the "Dean doing something wrong" part starts:

Dean doesn't feel good about it, but he agrees to keep quiet, because he's scared Sam will yet again make a suicidal play. Dean is riddled with guilt in the following episodes over lying to Sam, and in 9.08, Dean tries to tell Sam he's possessed, but Gadreel takes over Sam's body and stops him. Dean comes clean again in 9.09, only for Gadreel to stop Sam from receiving the news again.

So. Dean's mistake is lying to Sam. He shouldn't have lied to him. Point blank. At the same time, had Dean pushed the issue, would Gadreel have been willing to be expelled? Would he ever have allowed Dean to tell Sam the truth, from the moment he was... installed? Or was Dean screwed from the beginning, and was the idea that he got to choose any of this—any bit of it—really just... an illusion to keep Dean compliant with the possession that was keeping Gadreel under the radar?

Think about it for a second. Why did Gadreel ask Dean's permission? He didn't ever need Dean's permission to do any of this. He didn't need Dean's permission to trick Sam. He didn't need Dean's permission to remove Sam's memory of the hospital. He didn't need Dean's permission to keep the fact that he was possessing Sam a secret. He could have done every bit of this without asking. The problem was, Dean probably would have caught onto the disappearing angel act, and Gadreel would have had to get violent, and for the first part of season 9, Gadreel doesn't want to get violent! He just wants a place to lay low, and sees an opportunity to prove he's a good angel who helps humans—not just the angel who let the serpent into the garden. Getting Dean's "consent" might ease his own conscience about nonconsensual possession or be a way to keep Dean compliant or both, but ultimately, these are more questions worth weighing imo, because Supernatural loves to toy with the illusion that Dean has power in situations where he doesn’t, and in this case, he doesn't... actually have any power at all... does he?

That said, when it comes right down to it, Dean still did something wrong by helping keep the secret—by not trying to tell Sam the truth immediately because he was scared. And well. Okay. So what?

This is a show with characters who have good intentions but still make mistakes. As Cas will say about this later, "You were stupid for the right reasons". We get some great insights into the pitfalls that lead Dean down this path, and it's interesting to watch that happen and then later, see a broken mirror as Sam endeavors to prove through season 10 what Dean is willing to do can't touch what Sam is ultimately willing to do to keep Dean around.

Here's the thing—I don't believe for a single second that Sam wouldn't do the exact same thing in 9.01 had their positions been reversed. Sam and Dean have a conversation along these lines at the end of 9.13 "The Purge":

This genuinely wounds Dean and gets brought up a few times, but then in 9.23 when it's brought up for the last time in another context:

Sam never gets the chance to do the exact same thing to Dean, but he has already gone behind Dean's back to try and save his life before. He's used Dean's death to justify doing things Dean begged him not to do on his behalf. He kept the case they were actually on under wraps as he inched toward a plan to turn himself and Dean into Frankenstein's monsters in 3.15 (and really the only reason it didn't work is that Sam got captured by Doc Benton and Dean had to save his ass, and then Sam morosely helped dig the grave). Sam went behind Dean's back directly against his wishes to threaten a crossroad's demon in 3.05. In season 10, he violates Dean's consent by removing the Mark of Cain from Dean's arm using the Book of the Damned, which not only requires an overt human sacrifice of Oskar and gets a woman named Suzie killed in "The Werther Project" because Sam refuses to heed her warnings, but also results in the apocalypse... and all of this was something Dean asked Sam not to do, and Sam did every bit of it to get his brother back, and while standing in the wreckage in 11.01, echoed Dean's line from 9.13, saying, "I would do it again". Dean signed the supernatural possession next-of-kin consent form, and the fallout was Kevin and Sam. Sam violated Dean's consent and tens of thousands of people died and he said he'd do it again while they died around him.

I’ve seen a lot of your posts about cas having communication issues and it being a character flaw, and a lot of it with dean specifically which causes a lot of the conflict in their relationship. Do you think his communication problem is a result from him not being human and not fully understanding how to communicate as one, or that it has to do with how strongly he grows to care for dean so he hides things with the mindset of protecting him. I started wondering about the latter just because it seems like in season 5, once he is fully on their team, cas is very blunt and straightforward with his thoughts and feelings, often being shown as one who does not lie very well, but it changes after the season 5 finale. It makes me wonder if that’s when cas really fell for dean so it started holding him back from truly communicating with him. Or maybe you have a different opinion on the reasoning altogether, I was just curious on your take

I think it's a combination of things. One is absolutely that he (I personally think in a somewhat misguided way) wants to protect Dean (and his friends more broadly). In 6.20, Cas talks about coming to Dean's house and almost asking him for help, but being unable to bring himself to ask when he thinks of how much Dean has been through and realizes that Dean will uproot his life to help him.

Cas doesn't want to put Dean through another apocalypse. And when he initially agrees to work with Crowley and Crowley suggests bringing Dean into the loop, Cas reiterates that Dean is to be left alone.

The thing is, trying to protect Dean isn't the entire picture. Season 6 is riddled with Cas slowly making concessions, and one of the very first ones he makes is turning a blind eye to Crowley forcing Dean to work for him. So it isn't all about protecting Dean. Excluding Dean is also about trying to prove he can handle all of this by himself, and feeling shame if/when he can't or when he has to make moral compromises to achieve his goals. Crowley digs into Cas's hubris in 6.20 when he says:

Crowley paints a picture of Sam and Dean needing protection, but also of Cas being needed, and being powerful enough to do it all on his own—telling him he is special and worthy and deserving. Hubris is never far from lack of self-esteem. Buttering Cas up like this works because deep down, Cas does not feel secure and needs to believe that he is worthy and righteous. He seeks that feeling of worthiness from God, from the other angels, and from Dean at various points throughout his life.

One of the places we get the shame angle from Cas is in 6.03 when he first tells Sam and Dean about civil war in heaven and explains why he never reached out for help.

Cas was not successful at playing sheriff and whipping heaven into shape. He thought God was behind him because God resurrected him, but things didn't work out in his favor instantly. Raphael appeared as an adversary. So maybe God wasn't really behind him. Maybe Cas wasn't actually that special after all. Season 6—as much as it features a fallout between Dean and Cas—is also a fallout between Cas and God, as Cas slowly realizes that God is not watching him and cheering for him (anymore), starts to resent him, and then tries to replace him.

I think when I look at the show more broadly past season 6 and the other instances where Cas hides things and tries to do everything on his own, those instances tend to carry these same themes of Cas desperately wanting to protect the people he loves, but also being desperately insecure, looking for other people from God to the angels to Dean to give him validation. Cas tends to try and gain that validation through missions/ quests that make him worthy and deserving. And the idea of needing help with those special, holy missions feels like failure, because then he wouldn't have done it all on his own. When his missions fail or he isn't able to do it all on his own, it chips away at him slowly but surely. Cas all but tells us this in 12.19 "The Future". He talks about a range of failures he's recently suffered—some of them involving not being able to protect Dean or save Dean, some involving the larger holy mission (to protect humanity from cosmic threats) and he says he was trying to do it all on his own and that he shut Dean out because he needed a win on his own.

I also think the way Cas approaches these sorts of discussions—first saying the win is for Dean (just like in 6.20 when he says he did everything for Dean) then admitting that the win is actually for himself—he's also revealing that he has trouble admitting to himself that hubris is ultimately a part of his motivations when he does things like this. He tends to tell himself he is just trying to keep his friends safe or that they need him to prove himself, but deep down, it's that Cas is insecure in ways that have little to do with his friends, and everything to do with his upbringing and being uprooted from his life and not knowing how to feel worthy without a mission to serve because serving the mission is what he was brainwashed to believe made him worthy and deserving for his entire existence. After leaving the heavenly cult, he replicates the experience of using The Mission as a means of receiving praise from others as confirmation that he is worthy. (Which would be why one of his visions of paradise in the 12.19 draft script is himself shirtless looking poweful with his wings on display and Dean thanking him).

All of that said... I do also think Cas is sometimes just impatient. I mean in some ways, this connects to hubris, but I think keeping people informed about his whereabouts probably does sometimes feel like a chore to Cas. If it's something he truly believes he can handle on his own no problem, he sees involving his friends and dealing with their questions as an inconvenience, and he's very sure that he is going to succeed and be back before they ever know he was gone. And sometimes he's right. But he is also sometimes very very wrong, either misjudging what he can accomplish on his own or failing to account for the unexpected. Then he gets himself into hot water and Dean is upset (or the angels in some cases), and that means Cas fails the mission and still feels insecure and loops back to looking for another mission that will prove he is worthy and deserving. The problem being... you can't rely on other people to give you your self esteem and also need to actually be self aware about your own limitations. And all of that is neat.