I am fond of Dean/Castiel that deals fairly with Sam, and I like Castiel as a character a great deal. That said, anyone have a line on a story in which, post-apocalypse or post-apocalypse averted, Castiel makes a move and Dean decides that part of being a functional grown-up is not sleeping with people who beat you up when you anger them? (Along with not beating other people—Sam—up himself, of course. Dean hasn’t exactly covered himself with glory on the domestic violence front, but this is a season of change.) I mean, if Castiel’s model for human relationships is the Winchesters, I’d recommend therapy first, at least.
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So I don't think Dean would take Castiel or Sam beating him up as the biggest clue that hey, maybe there are some unhealthy aspects to these relationships... kind of like what I said about the incubus story about Dean as a soldier and his body as a tool and his relationship to violence--I just don't think it would register for him that he and Castiel shouldn't be together simply because Castiel beat him up in and of itself, because Dean has spent his whole life beating people up and getting beaten himself. Just because he didn't beat Castiel up (leaving aside the stabbing and all the emotional crap those two have put each other through in canon) doesn't mean Dean would ever see himself as the victim and Castiel as the perpetrator in their relationship, because they both act out in the same way. In other words, it's the sadomasochism that's the issue, not who happened to be inflicting the pain.
In fact, their relationship wouldn't even be the main issue; that would be Dean's own relationship with violence and all the emotional sadomasochism and abuse. I feel like it would take someone he cared about getting upset with Dean hurting them and calling him on it--or at least, Dean would need to be able to have a truly intimate relationship with someone who didn't hurt him, for the first time--for Dean to undergo the kind of shift in his awareness where he might realize that not only is it not okay for him to do that to others, it's not okay for Castiel or whoever to do it to him either.
However, I think that kind of change is very difficult and complicated and you'd have to really sell it to me in the story... just like quitting drinking or whatever, I don't think those realizations happen simply because people decide they want to be functional grown-ups now. And Castiel is still barely a human at all, so I think he'd have his own journey to go on before he and Dean could be together after Dean started examining all this shit. Which isn't to say that it couldn't happen, just that it would be epic and they'd both have to change before it could.