Lol I'd judge on if he has good style/taste, and if not I'd give him pointers. Of course I'd be taken by surprise at first because I wouldn't be expecting it but overall I wouldn't really care. Then I'd follow up to ask him if he's transgender or just a cross-dresser because id be curious
I would be cool with it. But I love drag and I'm totally cool with cross dressing. I love Eddie Izzard and Grayson Perry. You don't have to be gay to dress in clothes opposite your gender, like Eddie says 'it's not a woman's skirt, it's my skirt'. So yeah, I'm cool with that.
Smile ask if he was confused about his gender? If his outfit was on point, tell him he is slaying his outfit. I don't know if it's a joke and he's bored with life so I would be kinda mad but not really. I would continue hanging out with him though.
I would be cool for like 5 minutes (I would expect I was being punked) I wouldn't be angry. I just don't know if I would be ok being with a man in full make up and girly clothes simply bc I don't necessarily like very feminine men.
OMG!!! O. O I might try not to laugh, but ask him if he went to a costume party before he came to see me lol if no I think i would just go on with the date but tell him that dating someone like that long term isn't something i'm interested in
Is he any good at looking like a woman? If he is, I'm continuing the date, maybe asking later in that date why he's wearing the clothes, not like "wtf why are you dressed like a girl" but bring it up in a conversation about my LGBTQA friends like "... And that's why you should never tell an asexual person to go fuck themselves. *cue polite laughter* If I'm not being to nosy, do you mind me asking why you wear women's clothes?" And if they don't want to say, well ok then.