By any remotely sane standards, Castiel is nothing to be trifled with. A literal angel of the capital-L Lord of the order Seraphim with an entrance that is absolutely the most memorable in the series, he strides past demon traps and across iron, exploding lights and not even flinching at a full blast of rock salt and a demon knife in the chest before calmly showcasing a twenty foot wingspan. He can push back against a Horseman while wounded, smite demons with a touch of his hand, and gank a diner full of Mother Monster’s hippest new backup dancers with a single gesture. His true form is a Lovecraftian horror the size of the Chrysler building, he’s millions, maybe billions of years old, with a list of superpowers that would be impressive in the Marvel universe, and even if he does happen to be wearing a thirty-something radio ad salesman, he wears him - and his trench coat - damned well.
Overall, it’s a fairly decent set of credentials, and that’s not even remotely a full list. So there really is no arguing that he’s a certified badass, and that’s something that Dean generally respects. During seasons 4 and 5, he definitely seems to. Yes, he nicknames and snarks and sometimes snaps at Cas – especially at the beginning when, perdition-raising notwithstanding, they are basically antagonists - but no more so nor in any particularly different tone than he does anyone or anything else. Besides, for Dean Winchester, snark is right up there with breathing, and the apocalypse kind of puts everyone on edge.
All that changes with season 6. They’re post-apocalyptic, and while Cas has his unknown thing going on in Heaven, he’s still around when called. What’s more, he makes it clear very early on that it’s no longer any form of obligation; it’s because he has a “profound bond” with Dean and WANTS to be there and to help them. And it’s right about then that Dean’s manner of addressing him takes a radical shift.
Sissy. Child. Baby in a trench coat. Quite a few others, including several times - notably and repeatedly after he sees Cas get an erection in response to porn and kiss the smoke out of Meg - junkless. His whole attitude and tone change. He’s demeaning, infantilizing, and borderline out of character, completely inconsistent with the way he talks to or about any other friend or ally he supposedly respects. So why the sudden need to not only tear Cas down, but specifically and repeatedly desexualize him?
Because the emotions, desires, and responses that got dismissed and back-burnered because the world was about to end are still there. Because CAS is still there. Because for the first time in his life, he had a serious relationship (Lisa) that he can compare those feelings to, and there are too many things that line up there and don’t line up with the love and loyalty he feels or felt for other family and comrades like Sam, Bobby, Rufus, Jo, or Ellen. Because Balthazar and Gabriel and Cas himself prove that angels are not actually asexual. Because it’s gotten blatant enough that other people have started saying things.
I don’t believe that Dean actually gives a shit that Cas is in a male body. Yes, I think he’s a strongly het-leaning bisexual, but that’s not even why. We’ve seen him too often be too genuinely accepting of non-heterosexuality for me to buy that he would be that horrified by developing serious feelings for a male-presenting being (particularly reinforced in 8.13 when he is totally fine being flirted with by another guy in a way that doesn’t in any sense threaten his masculinity vs his heterosexuality).
What I DO think is terrifying to him, however, is that his raging effemiphobia relies on a zero-sum binary that says in any intense and especially romantic or sexual relationship, regardless of the sexes, someone is “the Butch” and someone is “the Bitch.” The Butch, no matter what genitals they have, is strong, dominant, authoritative, the protector. The Bitch, no matter what genitals they have, is weak, passive, obedient, and needs protection.
And Dean, even beyond his serious self-esteem issues and general perception of himself as worthless, takes for granted that he’d be The Butch in a relationship with almost any woman and certainly any civilian (automatically weaker than a Hunter) as he clearly was with Lisa. But when there are two males involved, it becomes a matter, to an effemiphobe, of who is the Manlier Man, and Dean is all too aware that in a metaphorical dick-measuring contest with a soldier of the Heavenly Host…well, there’d be no contest. Which means he’d be the Bitch, and the idea of that kind of weakness is worse than terrifying, especially at a time when Sam, Lisa, and Ben all legitimately need his protection and Cas’ protection and attention are clearly unreliable and divided. If there is one lesson his entire life has drilled into Dean, it’s that he cannot, cannot, cannot under any circumstances afford to be weak.
Yet he also cannot, apparently, simply walk away from Cas or mentally box them as Just Friends…as he later proved quite able to do with Benny, difficult though it was. His feelings for Cas are too strong. If he could tear himself away, there would be no fear of winding up the Bitch, no need to bring Cas down every chance he could even as they grew closer, escalating more and more over the course of season 6 to the point of being painful to watch.
Then comes the great betrayal of “The Man Who Would Be King” and the awful spiral that rips through Dean and Cas’ arcs both individually and with each other from there to 7.02. Dean tries his damnedest to save Cas, even when he commits the ultimate - and everything in the history of the series would say unforgivable - sin of deliberately and horrifically hurting Sam. Cas reaches out again and again to Dean, swearing that it’s all meant for the best, begging to still be loved even as he makes one terrible decision after another. It’s a gut-wrenching series of episodes; all the more painful because it’s being driven not by outside forces, but by the characters we know and love the most dearly and with nothing but the best intentions.
Most poignantly in the scene when Cas breaks through the defective angel warding to visit him at Bobby’s, but a few times after that as well, Dean tries to “man up” and take charge with Cas, playing the card of their intense but ill-defined relationship directly and attempting to order him to stop. When Cas all but pets him on the head as he refuses, it’s a confirmation that John’s nastiest accusations were right all along. He’s the Bitch here. He’s not strong enough, not good enough, not manly enough.
And from his point of view, that failure of masculinity costs him everything. By the time the dust settles, Cas is gone, Lisa and Ben are gone, Sam is shattered, he’s crippled, they’ve lost their home at Bobby’s, they’re on the run, and even the safety they bought the world by stopping the apocalypse has been jeopardized by the release of the Leviathan. It’s his absolute worst nightmare come true, and if only he’d been strong enough - MAN enough - to make Cas submit to him, it would all have been preventable.
It breaks him. In a way that nothing we’ve seen before has done; in a way that literally all the demons of Hell and all the angels of Heaven and losing his brother and the apocalypse itself couldn’t. Attempts at bolstering his masculinity are half-hearted at best. He literally has to remind himself out loud that he’s supposed to want sex. When he loses Bobby too, he hardly seems surprised. By the middle of season 7, only Sam’s rapid decline and the need to avenge Bobby on Dick Roman (and holy shit, could they BE any more blatant with the toxic aggressive zero-sum masculinity metaphor with THAT character and his rise to power as our heroes lose their own potency…down to the LITERAL one chink in his organization being a woman who doesn’t need or want dick?) seem to be keeping him from drinking himself to death and not even caring.
But then, as he’s making a last, desperate push at filling Bobby’s shoes to save his dying brother, he finds Cas again. And this time, Dean is “the Butch.” He’s able to protect Cas from being exploited by another demon - Meg – as he was by Crowley, and to dominate that demon and dictate the rules to her. Once again, he gives Cas orders, and this time Cas obeys…and Sam is saved. Yes, by all appearances, the cost is Castiel himself, but it gives a kind of closure, and more importantly, it gives Dean hope for the first time since he broke to Alastair in Hell that he might, for once, be Strong Enough. Good Enough. Man Enough…but only if he cuts himself no slack at all ever.
It is at this point - particularly after we add helpless, androgynous little Kevin Tran and the Angel of Loose Marbles to the mix and he gets to do a little more pushing around of Azazel’s daughter - that Dean shows a fascinating change. He’s no longer despairing that he cannot be strong enough, and he’s been given his brother back, but he has still been gutted by the cost of his ‘failure’ in the horrible losses now including both Bobby and the Cas he loved.
For the next five episodes, he bears such a terrifying resemblance to his father that I strongly suspect that Jensen was deliberately referencing Jeffrey Dean Morgan’s performance. It’s a dark road, but it’s one that he knows all too well; the Winchester man who failed his loved ones once and now in penance must cut away all but the strength to protect the few he has remaining and avenge those he lost. His vicious, uncharacteristic growl of “no one cares you’re broken” is as much a reminder to himself as it’s an echo and quite possibly a quote of his father. I would not even have been in the least surprised if it was his intention after killing Dick Roman to try and give himself back to Hell in exchange for Castiel’s sanity.
Then Purgatory happened.
I’ve gone into what I think that time meant for Dean’s character in great detail here, but for the purposes of this, what’s relevant is that he received tremendous validation of his masculinity and was again placed in a position where he was circumstantially able to “be the Butch” with Cas. He overcame Cas’ efforts to protect him and instead lead he and Benny through Purgatory and almost got all three of them out…and Cas later validated that he did, in fact, succeed for all intents and purposes. It has relaxed him, taken the pressure off, and is allowing him to explore more of himself, including an intimate ease with Cas in both 8.08 and 8.10 that we’ve never seen before except for possibly a brief glimpse in 5.03. There was a clear sense that it was Cas and not Dean holding back, on edge, and with something to prove in their interactions.
However, as I said in my first meta on Dean and effemiphobia, this is not a permanent solution. Dean now knows that he can meet his own criteria of being good enough, and that a relationship with Cas doesn’t automatically mean being “the Bitch”, but that doesn’t solve that an effemiphobic, hyper-masculine framework is a toxic, untenable means of measuring one’s worth, and that it has only deepened Dean’s conviction that while he might be a good or even the BEST Hunter, he’s still just “a grunt.” Fortunately Sam - who has a far healthier framework about both gender role and self-esteem - has clued in, and as of 8.14, made it explicitly clear that he’s not going to let this drop.
Which is why I’m actually as a Destiel shipper glad that Dean and Cas are being kept apart for the time being. Right now, they are both very vulnerable to their own feelings, and if it weren’t for Naomi’s meddling, I honestly believe that the scene at the car in 7.07 where Cas revealed the truth about Purgatory might have damned well ended in a kiss. And that would have been bad. Dean’s exploratory and growing self-confidence would click tidily onto Cas’ shame and guilt and angelic instincts to obey, and they’d enable each other right into a very unhealthy mess that would only exacerbate both their weaknesses and damage until it imploded.
Cas needs a redemption arc that allows him to forgive himself, and he needs to learn that free will doesn’t simply mean burning the original orders and writing new ones signing himself over to a different master, cause, or thing to fight. He needs to stand up for and have a sense of worth in himself as his own entity. We don’t know the details yet, but it’s pretty clear that this is what the Naomi arc is going to be about.
At the same time, now that Dean believes he has value at all, he needs to learn that he has value for more than just the size of his blade and balls. He needs to accept that things like his geeky and domestic sides are worthwhile parts of him, not something he can “earn” with enough badass “points,” and that he can have a relationship that isn’t a zero-sum binary hierarchy. His most important relationship is, of course, with Sam, and the protector/protected nature of that has inadvertently reinforced his effemiphobia so much that no progress can really be made on any other relationship until that one becomes truly equal…but with the Hellgate arc and the intent expressed in Sam’s speech at the end of 8.14, that seems to be where they’re going.
If Destiel happens, it’s not going to happen quickly, and it shouldn’t. It’s the changing of the deepest-set patterns of their entire lives and systems of self-value for both Dean and Cas in ways that have nothing to do with something that is as irrelevant to both of them as sexual orientation but have everything to do with them becoming better men. It’ll be two steps forwards and three steps back. There will be so close and goddamn you idiots and throwing things at the TV. Dean will posture. Cas will obey. They will hurt each other and save each other and hurt each other again. They will stare at each other like water, like oxygen, like need drawn tight in every shade of jade green and cobalt blue dilated dark, but Cas will feel unworthy and fallen and alien and not want to overstep and Dean will be afraid of being weakened by love and need and that deep down he doesn’t want to dominate Cas and doesn’t want to be dominated and doesn’t have a third option of equal partnership truly formed yet. And they’ll look away. Square shoulders. Ruffle wings. Lick lips. Shift weight. Pretend nothing happened. Let time pass. Live through another almost lost everything. Try again.
If it’s done right, it’ll take at least another full season, because it’s not just teaching poetry to fish, it’s expecting them to write it while performing classical ballet…but if any carp in creation can give us a sonnet and a pas de deux, it’s these two. They have already shown that they are driven by a depth of love that has kept them trying when anything and everything says to quit and walk away from each other, and where there’s free will, there’s a way.