The canonical feminisation of Dean is so fascinating. I don't know a single other piece of media that's ever done anything like it. Sometimes it's subtle and subtextual, but often it's the polar opposite.
There's the parentification of Dean into the role of wife and mother.
Dean being literally forcefemmed sexually by Rhonda when she makes him wear pink panties.
The way people talk about his looks, like Gwen saying he 'has delicate features for a hunter'.
Azazel calling Sam 'son' but calling Dean 'daddy's little girl'.
'Daddy' is more utilised by female characters than male, often to signify youth, innocence, and naivety, but it crops up often for Dean. The above from Azazel. Dean's own subconscious calling him 'Daddy's blunt little instrument'. Most strikingly, Henrickson saying 'Daddy brainwashed you with all that devil talk and no doubt touched you in a bad place'.
And that last one, the little remarks and plot points that time and again suggest Dean is a victim of CSA. The 'nobody's a virgin' line. The way he is paralleled with Bela. It's rare that male characters ever get this treatment.
It's just such fascinating characterisation. On the surface, Dean is all tough-guy machismo: he drives a cool car, wears a leather jacket and work wear, listens to metal, drinks whiskey, and is chillingly comfortable with violence. But this is so often framed as compensation for the fact that underneath it all, he's just a traumatised, damaged kid who grew up too fast and has suffered through countless horrors.
And he's Daddy's little girl.
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