I’m 36, and my ten-year marriage ended last year. I’m getting ready to get back in the dating game, and I have a weird question: what kind of underwear should I wear? I’ve asked some female friends, and they’re about evenly split between boxers and briefs. They told me to ask you what’s hot on guys these days—and to ask if you have any tips for them (the women) while you’re at it.
Welcome back to the world of dating! It’s fun, I promise. I mean, you get to worry about things like what kind of underwear to wear! It’s funny that your friends are split between boxers and briefs on the underwear question, because the right answer is…BOXER BRIEFS! You can’t go wrong with boxer briefs. They are the right combination of coverage and support. They are sexy. On all men. Buy some now.
One of my male friends swears by PACT underwear and it’s earned rave reviews from the ladies who’ve seen it. Not only are the undies shipped in a compostable envelope, but each undergarment is inspired by a social or environmental cause and 10% of every sale goes to a non-profit! If there’s anything a woman likes better than a man with a well-packaged package, it’s a well-meaning man with a well-packaged package!
Some of the patterns at PACT are a little over the top, but you can find something that fits your style. Style is important in the dating scene. A man with style shows that he cares about himself and his appearance. Women spend time and money on looking good, and we like men who show some effort in that department. If it looks like you haven’t bought underwear since your mom bought them for you for Easter ten years ago, that can be a sign that you don’t have the time or ability to buy yourself something to cover the goods. And don’t you want to put some thought into the fabric closest to your man bits? Comfy, high-quality fabrics are important. If you take care of your junk, you’ll hopefully treat a woman pretty well, too. You can keep the ugly underwear or buy cheap ones, but have a few sexy pairs to wear when you want your privates to receive some attention!
If boxer briefs don’t seem quite right, there are some options such as “trunks” that are shorter and closer to briefs but still sexy. If you wear tight pants, or bike a lot, or both, underwear in the boxer family might bunch—which I imagine can’t be fun, so a shorter cut might be more comfortable. You can find boxer briefs or trunks most places (Target, Macy’s, wherever) so you can find a fit, fabric, and price point that you are comfortable with. But trust me, go with boxer briefs (or the boxer brief family) and you won’t disappoint.
As for the ladies, I tend to go with a fit that I find comfortable but flattering, which can vary based on body type. I find a lower-cut bikini style looks and feels best for me. It’s important to feel sexy, so finding something that makes you want to show off your bloomers is a good plan. I asked a male friend (since I often don’t ask for feedback on my drawers), and he thinks that simple is better. He recommends finding something that accentuates your body, not overpowers it and says that a good pair of panties should make your ass look great and expose just enough skin to accomplish that. If your ass looks great naked, wear a thong. If it could use a little lift, get panties that lift. Nice round cheeks? Get some hot booty shorts that expose your underbutt. And as he says, “Most men (with some notable exceptions) want to have sex with a person, not their underwear,” so find something that makes you feel hot and ready for a romp, and you’ll do well in the dating game.
Now go cover your crotch,