Well…
I, unfortunately, have not had the opportunity to sit down one on one with Jensen and discuss this. But, yes, I think if we could walk him through the reasoning, he’s understand better.
One thing that trips him up, I think, is that with Dean and men he plays certain things for laughs - Dean getting flustered and fangirlish and kinda gay. It’s funny, to him, to…idk if feminize Dean? Make him seem…kinda gay? But no matter the motivation behind the acting choice, even if it was a joke, that’s now part of the canon of Dean’s character so…we can make of it what we will.
I mean, come on, Phil and Ben talked about this on the Everybody Hates Hitler Commentary, about how Dean getting flustered by Aaron is funny but it shows the potential for love in all sorts of places.