You put a lot of work into getting to the point where you’re standing in front of a woman in your underwear. You do not want to ruin this crucial moment by making her stop and think about the drawers you’re wearing. If you don’t want the first time you’re with her to be the last time, evaluate your choices—STAT.
Boxers: Roomy and breathable, boxers are the choice for dudes who don’t mind not having a lot of support (or any). What they say: “I’m going to be adjusting myself a lot, hope you’re cool with that. And if you find these in my drawer, feel free to steal them to wear as shorts.” Reserved for: Manspreaders and traditionalists.
Boxer Briefs: Like the name says, they’re a hybrid of boxers and briefs, providing coverage and support without being obtrusive. What they say: “I’ve prepared for this moment and I’m gonna make you breakfast tomorrow.” Reserved for: Most normal guys—color and pattern is where you get to see the guy’s personality here.
Briefs: We’re not talking tighty-whities—we’re talking expensive bikini bottoms that leave nothing to the imagination. What they say: “I never miss the gym, I wear too much cologne and I spend $75 on t-shirts. It’s 4 am, you up?" Reserved for: Guys who like guys, Europeans and straight men who look in the mirror constantly.
Novelty Boxers: Oversized boxers emblazoned with hearts, frosty beer mugs, flames or cartoon characters—probably purchased at Spencer's. What they say: “I think I’m hilarious (“pull my finger” jokes are my specialty!). You’re cool with staying home again, right? I don’t wanna go anywhere.” Reserved for: Manboys.
No Underwear: Going commando, freeballin’—whatever you wanna call it—you’re flying free and loose. What they say: “I thought tonight was a sure bet,” or “The last time I did laundry was two months ago.” Reserved for: Guys who still haven’t grown up (and possibly never will).