I want Sam to come out to Dean as nonbinary, but Dean doesn't really know what that means.
So he says, "Oh, okay. Should I call you by a different name or something?"
And Sam goes, "No, I'm just telling you I'm not a man."
Dean still has no idea what's going on and says, "... Okay... Are you a woman then?"
It clicks for Sam then, and they ramble out a whole explanation about how they don't feel like a man or a woman, that they're something else. They don't quite know what exactly they feel like, but nonbinary is good enough to cover for it now.
Dean's kind of blown away by that. He never really thought you could just... opt out.
"So, what exactly is going to change? Are you gonna be wearing silk stockings with your steel toes?"
Sam rolls their eyes at the crass joke but otherwise ignores it. "I want to you use they/them pronouns for me from here on out. I don't want to be referred to with any gendered terms like man or brother."
Dean's face kinda crumples at that, so Sam rushes to tell him, "Person is fine. Or sibling."
"That's kinda awkward to say, isn't it?" Dean asks.
"Only if you make it awkward." Sam says.
Dean swallows thickly, fiddles with his fingers. He obviously had something on his mind.
"Just ask, Dean. It's okay," Sam reassures him.
Dean sighs. Clears his throat. "Can I still call you Sammy?"
"Yeah, Dean, of course." Sam smiles at Dean and feels relief when Dean smiles back.
So Dean tries his best. There are still some half formed "little bro-"s that come out, a few "he-- I mean they"s overheard while Dean's on the phone. But he only does one or two double takes when Sam paints their nails or their eyes, holds back the stupid comments when Sam's wearing something more feminine than usual. And that's what matters.
And then, when Dean's making fun of Sam for something, maybe about their salad or their exercise routine or whatever, and says as smooth as anything, "Where did I go wrong with you, little sib?"
Sam feels like they're both okay.