I think one of the main reasons why Dean as a character speaks to me and fascinates and moves me is based in how he imo defies stereotypes, categories and labels. Of course you could attribute certain characteristics to him, but to me the decided difference and important aspect is that with Dean it’s not an “either-or”-thing, he isn’t “one or the other” or “this or that”. He is a lot of things that many people tend to categorize, label and see and treat as mutually exclusive. Though they really aren’t at all - Dean Winchester proves it (and so do tons of real actual people too):
Many characters within Supernatural have focused on Dean’s “good looks”, even tried to make him uncomfortable or insecure about it and paid the price for mistaking Dean as “just a pretty face”. And that’s what I love about Dean. He can be tender and sweet in one moment and a badass and ultra skilled and badass hunter in the next. He isn’t ashamed to show emotions, has been crying openly on many occasions and has proven to be a very sensitive and empathetic person and at the same time he can be relentless, unforgiving and bottling up his emotions. He is a tough as all hell hunter and skilled fighter and yet has managed to preserve some childlike glee and is not ashamed to admit that he gets starstruck when he meets his childhood hero and favourite wrestler or with incredible passion delves into LARPing. These aspects aren’t a product of uneven and lackluster writing (most of the time - of course there are exceptions), it’s the reason why Dean imo is one of the most layered and facetted fictional characters that’s ever been created (and part of the depth Dean has is absolutely due to Jensen’s ability and talent) and fascinates many people (partially because he serves almost as a “canvas” that many people can project themselves into an find something in Dean that they can relate to or latch onto for lack of a better word).
He proves and shows that there is no discrepancy between being a tough guy when the situation calls for it and an incredibly empathetic and sensitive person at the same time. None of those things have anything to do with gender or sexual orientation, but simply with the character of a person. And I love that about Dean. I love that even though he is being confronted with labels left, right and center and certainly also uses them himself (we all do consciously or subconsciously) he is much more than he himself is aware of - though Dean has become quite self reflective over the years. But mostly I think he ain’t someone to overthink himself, he just is. He is a guy who loves his car and a couple of beers and whisky, but he is also someone who likes to dress nicely and appreciates a home cooked meal. And this diversity, this amount of to some people whether in RL or fictional life “seeming” conflicting character traits aren’t standing in any opposition to each other at all. They just make one pretty well rounded character. A character I fell in love with faster and harder than with any other fictional character before.