Me neither. Normally I'm pretty good at interpreting retard speak but what in the literal fuck is he trying to get at? Even in his retarded kweer social circle I've never heard this sort of sentiment. The point is that if you want to wear a dress and "express yourself" or whatever, fine. But what woman, even the woke ones, actively want or encourage their partner to do that? Makeup...facials...what the fuck, women aren't trying to get their male partners involved in these rituals. If I had a dollar for every time one of my girlfriends lamented "Ugh I want to get a pedicure but I really wish my boyfriend would come with me" I'd be even poorer than Chibi.
And if he's trying to imply she'd be self-conscious wearing a dress in public (???), pretty sure the absolute last thing she'd want is some lumbering, fat, blue-haired, greasy manchild wearing a fugly, ill-fitting Pokemon dress to draw everyone's eyes to the freakshow.
Honestly the tweet only makes sense if you read it as him trying to court a tranny.