When to Tell Someone They Might Be Gross

by A Lady

Dear Hairpin,

So, I am still friends with a guy I dated for a while, like, a decade ago. We get lunch or dinner a couple times a year and catch up. He’s been pretty much single since then and is bummed about having a hard time finding a girlfriend (he wants to be in a committed LTR hopefully with marriage and all that jazz).

I’m pretty sure one of the things keeping him from finding someone special is that 1) he dresses the way he did ten years ago, like badly matched sort-of Goth attire that doesn’t fit, 2) he often, like every time I see him so I’m extrapolating that it is normally this way, smells kind of bad, for whatever reason, I think maybe lack of attention to things like dental hygiene or being sort of musty or whatever, and 3) is generally unkempt and kind of gross, like has gross dirty fingernails.

There are other reasons that I can see why the ladies would not be all about him, but they all fall into the category of Harmless But Annoying, and he’s a decent, kind guy who would make a loyal and affectionate boyfriend. But I can see that it would be really hard for someone to look past the surface crud when they meet him.

Soooo, I’m wondering — first of all, when someone sadly comments about how hard it is for them to find someone and seems to be genuinely bewildered about it, is that the time to just nod and murmur comfortingly, or, after enough years (YEARS!) of this have gone by, is it permissible to say something? I’m not asking him to change his sort of geeky but mostly adorable personality, just to clean his fucking fingernails. It’s a little infuriating that something so basic seems to escape him. Can I say something like “hey you have a great personality and are kind and funny and everything, but you smell like a wet hamper and that is probably also preventing you from finding a lady?”

I mean if there were something like that about me that I could easily fix, I’d like to think I’d want to be told, like I want to be told if I have spinach in my teeth or whatever. I also see him infrequently enough that if he took total offense it wouldn’t matter all that much, and in general he’s not an offense-taking kind of guy.

Isn’t this everyone’s nightmare? To be one of the musty-smelling people? But although it sounds like this guy really could use some general/objective tweaks, it’s also possible that he smells delicious and excellent to someone else, right? Which is why I’d hesitate before telling someone they smelled bad. Some people’s B.O. smells hot to me, but then other people — clean people — generally smell revolting.

But anyway — and I guess this is obvious — if you really want to say something, think of how you’d like him to say it to you, if you were the gross one. And maybe you are! We’re all gross. If it were me, the next time he complained about finding people to date, I’d say, basically what you suggested, “Dan, I realize this might be kind of out of line, but I’d hope you’d do the same for me, so I’ll just say it — you are handsome and awesome, and women might be able to see that more immediately if you showered a little more and cleaned your fingernails! And now is when you tell ME that I could stand to use more deodorant, or whatever, by the way.” It’ll be awkward, but maybe not as bad as you think, and then ideally you could find a way to laugh about it or something else right after.

I don’t think you have to mention the clothes, though.

Or the next time you see him, you could pretend it’s a funny and startling new thing you just noticed. “Whoa, haha, Dan, you smell! Are you showering?? Haha, I love it, you’re so gross.” Or like, “Oh my god, Dan, your fingernails! Hahaha, oh my god you have to clean those, you nutcase!!”

One other thing is that you don’t mention how the relationship ended, or what your dynamic is now. Because if you dumped him, it might be trickier — I’m now envisioning ex-boyfriends who broke my heart sitting me down specifically to tell me that I stink and dress like shit, and, wow, yes, I don’t know if I would like that so much, but also whatever.

Anyone have any better ideas?

A Lady is one of several rotating ladies. Do you have any questions for her?

Photo by Ina Schoenrock, via Shutterstock