Single Guy Confessions: I Bought Briefs For The First Time As An Adult And Now I’m An Ugly Old Man

Photo: AMC

It’s not the first uncomfortable single-guy confession I’ve made, but that doesn’t make it any less embarrassing when I tell you that I bought briefs for the first time as an adult, thinking, “Hey this could be fun.”

Before, I thought maybe I’d outgrown that awkward stage where clothes fit me all wrong, thinking maybe I could make briefs look sexy after an adolescence of boxers and an early manhood in boxer briefs. By the end of it, I was an ugly old man, and now I regret everything I’m confessing.

Come with me, explore the process on how you imagine this experience might go, then stick around for the unexpected, yet not that surprising, ending to a terrible idea.

Single Guy Confessions: I Bought Briefs For The First Time As An Adult And Now I’m An Ugly Old Man

I Just Turned 33, So I’m a Man Now, Right? Wrong.

With every year that passes, we get a little more of that unearned confidence that we’re getting wiser, making better decisions and changing slowly into the man we were meant to be, a great man. It’s not until you roll the dice on a new idea, like wearing briefs for the first time since you were 11, that you find there are limits to your new-age greatness.

The Evolution of Undies

As a boy, you grow up wearing tighty whities with fashion sense because your mother made you try them on over your pants at the department store. You still haven’t lived that moment down. When you finally got to pick out your own school clothes, you got your Tommy Hilfiger boxers or some cartoon bullshit you think is funny until you learn about the pubescent public erection.

You ride that out until you’re old enough to make your own decisions (kind of), switching to boxer briefs. Now you imagine once you’ve bought a car, a dog, maybe even a house, you’re confident but still young enough to rock briefs and make it look good. Your inner 10-year-old will soon enough laugh at your pathetic attempts.

On the Way to Buy Briefs

You realize you have a decent size list of things to buy, so you imagine it’ll go down at Target or someplace your mother would take you, if you’d let her. You start to text her, thinking it’ll be a funny throwback before realizing throwbacks aren’t your forte, deleting the text that, in all honesty, was just after advice, moral support and some reassurances that this would all go well. Your mother would have told you to hold off, sexy boy.

Getting Down to (Just Your) Business

You stand amongst the underwear racks, a myriad of senseless opportunities landing upon your wandering eyes. You start to enjoy the color combinations, wondering if you can rock red briefs in front of another pair of human eyes (your dog will never recover), only to dance around the idea of buying (jokingly, of course) the cheetah pattern. You put those back in shame when the mother next to you covers her son’s virgin eyes, quickly grabbing the standard Hanes and rushing to the backroom. Suddenly, you’re naked in a Target changing room before you remember that’s not normal.

The Trial Period

Thanks to a treat-yourself moment, you upgraded brands from sandpaper hugging your junk to something that’s actually comfortable and makes you feel a little sexy, kind of like the first time you tried on ladies underwear and thought, “I kind of get it.” Oh, was that not a universally shared experience? Moving on…

You get home and get a good look at yourself (yes, you wore them home and just scanned the package with your dirty underwear in them to the dismay of the people behind you) now that you’re in the comfort of your own home and in front of a mirror that never lies. You think, yeah, this is the new you. You’re a man, finally! It’s about damn time, but better late than never, right?!

Reality Sets In

The first girl who sees you in your briefs laughs and asks, “Dude, how fucking old are you?” Hope you kept the receipt, buddy.

Maybe briefs are for 34 and up, but we’ll never know until they label the goddamn things, or you work up the balls to ask your dad about the day he became an ugly, old man.

Expectation VS. Reality: Never Forgot


For more of the single guy experience: Single Guy Confessions: I Fell in Love With a Girl in a Craigslist Ad