That is, wife (43) and daughter (12). Told them I was re-evaluating myself and who I wanted to be, and that I wanted to try being "cuter" (didn't quite have the courage to go further), and that perhaps men's clothing didn't suit me.
The wife was mostly "yeah, right" -- seemed happy that I was trying to improve myself but seems to think it's just a phase (maybe it is? idk).
But my daughter was right on board! Came up with a load of outfit and makeup suggestions, and proposed going to an anime convention together, dressed up. I asked her if she'd think it was weird for me to go about dressed as a gothic lolita, and the response was "no, I think it'd be cute."
So next step is maybe cute anime girl cosplay at home, with an ally!
I'm literally shaking with ... excitement? fear? relief? I have no idea. Ohgodohgodohgod what am I doing...