Dear Captain Awkward,
My (he/him) housemate (also he/him) wears skirts almost all the time, both at home and other places – knee-length and baggy. Which, you know, cool. He also mainly wears boxers, the kind with a wide leg.
The problem is that because he’s only really felt comfortable wearing skirts for a few months, he doesn’t have a lot of understanding about what they do and don’t cover in certain positions. Add in the wide-leg boxers, and he’s accidentally flashed me a number of times.
I’m certain this is accidental. He’ll be in the wrong position before I even come home from work, and there’s no hint of him moving to a more compromising position when I’m in the room. Also, although I’d be completely fine peeing while he’s in the shower, or vice versa – we only have one bathroom – unlike most of my other cis male friends, he told me he’s not comfortable doing that.
I’m also certain that he would be completely mortified to learn he’s flashed me, and possibly other people.
But I also really feel like I should tell him. So he can get underwear which covers more and be mindful of sitting with his knees together. Plus to stop him flashing anyone who doesn’t know that it’s a wardrobe malfunction and thus feels unsafe when he’s around.
But… what words? What medium? How do two very awkward people have an even more awkward discussion? I don’t want to see his junk, but I also don’t want him to feel he should stop wearing skirts.
Thanks for any advice,