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#1309: My housemate is accidentally flashing me from MzHeather's blog

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,
Eyes averted.
Hello there, Eyes Averted!
I’ve been wearing skirts and dresses for 46 years, and sometimes they just don’t act right. Like the night I first met my future mother-in-law, for instance, when we were out at dinner, and I came back from the restroom not realizing I’d tucked the back of my skirt into my underpants and was giving the Lou Malnati’s dining room a sight they could never unsee. She noticed, and as I sat down, she leaned over and quietly said “double-check your skirt situation” or something similar. I quickly remedied the situation and thanked her for telling me. It was embarrassing, and there were many blushes and good-natured giggles to go around, but it was way less embarrassing for me and safer for my fellow deep-dish diners than if she hadn’t told me and I’d discovered it on my own later. She was brief, direct, and timely, and I appreciated all of that.  
Bodies are weird, and clothes are imperfect vessels, even for the fanciest people! Have you ever had your fly unzipped or accidentally had something hanging out of your shorts or swim trunks that shouldn’t be, and then had someone swiftly and quietly tell you about it? Like, “Hey buddy, the barn door’s open” or making that cross between a point and a wave gesture that means “Pull it together, friend”?  Have you ever had to do that with a fellow penis-operator who wasn’t in a skirt? What did you do or say? What happened afterward? I’m guessing here, but my strong suspicion is that it went fine. They told you, or you told them, everyone felt weird for a minute, and then the problem was solved. 
So, I think that’s exactly where you should aim, here. Next time you come home and accidentally glimpse your roommate’s undercarriage, say something right away, with the exact same tone you’d use if your workmate had their tie buttoned into their pants or toilet paper stuck to their shoe or spinach in their teeth: “Oh hey, how was your day? Whoops, hold up, your downstairs needs rearranging.” 
You’ll look politely away (throwing a hand up as you avert your eyes is a good non-verbal cue), he’ll fix it, he’ll probably be a little embarrassed and apologetic, so you’ll say, “No worries, it happens, and please always tell me if I’m giving you an accidental peep show.” Hopefully everyone will laugh sheepishly about it for a second, or bond over flashbacks to weird locker room moments, and then there will be a lovely subject change. 
In your shoes, I would also treat the next time as if it were the first time. If he doesn’t know it’s happening, then he doesn’t know that it’s a problem or how much overthinking you’ve been doing to avoid making him self-conscious about it. You get to restart the clock from the first time you say something. 
If it happens again? Because it probably will, while he’s figuring it out? It’s okay, you can do the same thing again, deliver the exact friendly, casual, helpful “Oops – wardrobe malfunction!” you’d want if a friend noticed your shorts were adrift or your fly was undone.
If it remains a serial problem after you speak up a time or three, that’s when to combine “Yikes, your skirt’s riding up again” (normal, calm, casual) with “Hey, I really don’t want to make it weird, but this seems to happening a lot? Maybe skirts require a more secure underpants situation than you’re used to?” Barring that, the less you make it about THE SKIRT and the more you make it about “clothes are weird, whatever, what were you saying?” the easier it will be. 
We all had to be taught to wear clothes, at some point, and I can recall approximately a million reminders about how to sit, as well as shopping trips for dance-briefs for show choir and slips for looking “professional” and finding bike-short-like solutions to prevent accidental butt-shows and chub-rub. I have, like, nine distinct kinds of underwear depending on what I’m wearing and where I’m headed and how I’m getting there! It’s not intuitive! It’s not strange that your friend would encounter a learning curve if he didn’t grow up in one of the many sarong, loincloth, robe, and kilt-wearing cultures on earth, where I presume parents give “how to dangle your jangles in polite company ” lessons, the same way they do with facial hair maintenance and tying a tie. There are many, many online guides out there for pants-wearers who want to branch out, and your housemate will figure it out. 
You don’t have to manage all of that for him or worry this much on his behalf. Telling him directly and calmly when there’s an observable problem, with the assumption that it’s unintentional and he’d want to know, is the way to be kind to everyone in your house, including your housemate, including yourself. Anyone who is truly doing this accidentally and who is some combination of self-conscious and self-aware about privacy and body parts (like a housemate who strongly believes that bathroom is alone time) will get the message and fix it ASAP. This is going to be okay. 
Comments are open. I want to hear especially from:

People who adopted skirt-wearing as adults: What was your “Not Accidentally Re-Creating Famous Subway Grate Glamour Shots” learning curve like? Where did you first learn The Good News about the boxer-brief compromise between freedom and secure containment? Did anyone have to helpfully remind you along the way? 

People with stories about being told about an embarrassing wardrobe malfunction and it going just fine.

People with guidance, examples, or strong opinions about when TO definitely say something vs. definitely NOT say something. I think my personal code, which I came up with just now, is built around a combination of “Is it fixable,” “Is it fixable fairly immediately” and “Can I tell them, and can they fix it, without making anything harder or worse.”

Example: A workmate’s sparkly necklace has become looped around one boob. She’s about to go up and give a presentation. I’d absolutely say “pssst, your necklace” or catch her eye and try to signal her about it if I could before she gets up there. Fixable! 

If she has already started her presentation? What necklace? There is no necklace. There was never a necklace. Maybe, if this thing is being recorded or broadcast, I find a way to interrupt or slip her a note, but otherwise I’m not going to interrupt her flow or draw attention away from her words if I can possibly help it. If it’s still tangled when she’s done, only when I could catch her privately in the hall or restroom, would l say “oh hey, your necklace,” as if I have just noticed it for the first time. If she asked how long it had been like that I would not lie, but I would also hope with my entire soul that she would not ask, so that she might be spared. 

If she had a stain on her shirt and would have to go home and change, that’s not immediately fixable, so I’d go with: Stain? What stain.

Where I learned this, I think: My very elegant, polished, Washington, D.C. boss once pulled a tampon (unused, thank Maude) out of her pocket instead of a laser pointer or pen during a client presentation, and began pointing out areas of the map on the slide with it. It had a blue plastic applicator and had come loose from the wrapper in her pocket, so it probably felt like a Sharpie or close enough, and she was very involved in what she was saying, so she didn’t notice for a while. The other women in the room froze, darting eyes at each other. I don’t think the men noticed, but if they did, they did not react. She eventually realized (the string was making a distinct shadow on the projection), said, “Oh” with a little laugh, tucked it back in her pocket, pulled out her pen, and kept right on going. 

In the Letter Writer’s situation, it’s fixable, it’s fixable right away, he’s stuck at the “oh no will I make it worse” stage, understandably, but at home, a quick “tuck yourself in, bud” isn’t going to shatter anyone’s world, which is why I’m firmly in the camp of “say the thing right now.” 

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