Jill Asks: Why do men prefer boxers over briefs? I happen to think that briefs are quite adorable and yet most men refuse to wear them. Flaunt what your mama gave you, I say! But seriously, why do men have such an negative/surprised reaction when I say, "I like briefs on a man"?
Jack Answers: Before we begin, let's make sure that we're all on the same page. When I reference "briefs," I'm talking about tighty-whiteys, OK? I'm not talking about boxer-briefs, as those are more like boxers than briefs (and boxer-briefs happen to be my underwear-of-choice, thankyouverymuch).
I also want to state up-front that there is a notable exception to the Boxers Over Briefs Rule: working out. Running, jumping, etc. while wearing boxers is about as fun as getting softly kicked in the junk over and over again, so every guy should own at least a few pairs of briefs for when he's physically active.
Now that the nomenclature is clear, let's get to the main point: there are only two types of dudes who should wear briefs on a regular basis: (1) dudes over 50, and (2) dudes who wear really, really, really tight pants. That's it. End of story.
Since I've been in my share of health club locker rooms over the years, I estimate that I've seen roughly 500 different men over the age of 50 in their underwear. And guess how many of them have been wearing briefs? Every. Single. One. Their commitment to briefs is impressive. So impressive that it's become a part of the uniform for the 50+ club. "Oh, look, he's wearing briefs; he must be one of us." Similarly to how I don't want to wear the same style of jeans that my dad wears, I don't want to wear the same style of undies, either.
The only other time it would make sense to wear briefs is if your pants were so tight that the excess boxer material bunched up and made it look like you were wearing a diaper. But since I don't wear TIGHTS to the office, this isn't really a concern of mine.
One other point worth noting: briefs look A LOT like girls' underwear (e.g., the "boy cut" panty at Victoria's Secret looks exactly like a pair of briefs). So maybe your obsession with briefs points to a bigger underlying issue that the two of us should discuss offline, perhaps?
In summary, if you're a fan of briefs, deep-down you're probably attracted to old men, really tight pants, and/or women.
There's something I've been wanting to tell you: I think maybe I'm attracted to old women in tight pants. I've thought a lot about your response to this question and I see no other possibility. I thought you should know.