Chat with Deb — Guys’ (?) Underwear

It’s the 2020s, and women are STILL forced to raid their boyfriends’ drawers?

Jack Herlocker
3 min readApr 4, 2022


Photo by author, because… did you ever search Unsplash, Pixabay, or one of the other CC photo sites for “underwear”? You will get a LOT of photos, most of them highly interesting to the average straight male, but none of them useful for this article (and some that are NOT underwear, sorry). Sooo… “mens underwear”? You will get many photos, most of them highly interesting to the average gay male [I would guess], but none of them useful for this article.

In a month, roughly, we will be in Vancouver, BC, checking out the city for a few days before getting on the MS Nieuw Amsterdam for our cruise to Alaska. We have been planning this since before we were married, and saving for years¹ to make sure we can afford it no matter what strange things happened before our 20th anniversary (which was two years ago, because sometimes stranger things happen than you plan; see: “COVID-19").² But this year, Nothing Will Go Wrong!³

Meanwhile, Deb is getting into Debster Planning Mode™.

DEB: How’s your underwear?

ME: (trying to put the question into context—failing) Fine? I guess?

DEB: We’ll be traveling for two weeks, and while the ship does laundry, you might want to take more underwear than you have right now. Y’know (pointed look) some good underwear.

My underwear is perfectly good, unless it has a hole. It’s not really a hole unless I can fit my finger through it. And by finger, I mean thumb. (Same rule for socks, but substitute “big toe” for “thumb.”) Okay, fine, even by that rule I don’t have enough for two weeks. So I go shopping. And by “go shopping,” of course, I mean “pull up the Amazon app on my iPad.”

ME: Underwear will be here tomorrow.

DEB: Wow. That was fast.

This is a week later. No, she wasn’t being sarcastic. Sometimes I like to think about things before I dive in.

ME: So I basically bought the same stuff as last time, as near as I could read from the labels. I also skimmed the reviews. The briefs got very good ratings, except from one guy who is in total despair because men’s underpants today aren’t like the “tidy whities” he had as a kid. Also, this time I paid more attention to the undershirt description. Last time, I just looked for “v-neck” or “crew” and picked the former; this time, I noticed some undershirts are “full coverage” and some are not.

DEB: I remember you complained last time that your new v-necks were too long.

ME: And at the time, I thought, okay, younger guys wear their pants lower, they want to have longer t-shirts. But then I realized those guys want to show off their boxers or whatever. And this time, when I read the reviews, half of them were written by women! And not moms who were shopping for their kids, although there was one of those. These were women commenting on how the guys’ undershirts fit them; comments like, “I’m 5'4”, 135#, and the M fits me very nicely, not too long, not too tight, but be ready for some shrinkage after washing. The material was nicely opaque without being overly warm.” So now I’m wondering if the longer undershirts were for women with low-rider jeans, or whatever? In which case, seriously, women still have to shop in the mens department to find basic clothing at reasonable prices? How does that make sense in the 21st Century?

¹Ladder CDs. Good for long-term goals.

²Yes, I know Putin is talking about nuclear war. Shush!

³Note to Universe: this is a comment, not a challenge. Be nice.

Conversations with My Wife are now “Chats with Deb.” I’ve been posting “Conversations with My Wife” since 2016. Medium’s latest design changes involve dropping the subtitles from references, while also truncating long (?) titles, so I am now putting the subtitles into the title and shortening the series name to “Chats with My Wife.” Well, I was until Mark Starlin suggested “Chats with Deb” to make it even shorter (“I think most of your readers know you two are married by now. 🤣 And that you are married to ‘Debster.’”). So I’m giving that a try. Comments welcome.



Jack Herlocker

Husband & retiree. Developer, tech writer, & IT geek. I fill what’s empty, empty what’s full, and scratch where it itches. Occasionally do weird & goofy things.