Hey Woody!

Do you think the right underwear can get you laid?  I have a friend who has an unbelievable collection of “funderwear” and swears it’s like a pheromone for guys once he gets them in bed.  On the off chance he isn’t insane, what would you recommend I wear to turn guys on?

—  Lingering around the lingerie

Dear Lingering:

My rule for men applies to underwear:  Never put anything on your crotch unless it feels good.

Here’s my take on making the c-ckcrazy sl-t come out of your date:

Contour Pouch Briefs

Like my last boyfriend, snug but not uncomfortable.  And like my last boyfriend, provided little support.  The pouch doesn’t have a fly, which means when you siphon the python at the urinal you’re going to have to do some side digging.  Pretty hot looking, though.

Nylon Briefs

Because the thin nylon material wrinkles and bunches up it tends to make your package look smaller.  Hey, did you feel that breeze?  It was everyone’s eyes going to the next paragraph.

Basic Briefs

The urine-stained standard of the last 18 generations.  Unfortunately, “tightie-whities” are as boring as watching a gay movie (why are the only good gay movies made by straight guys? WHY?!).  S–t, now I’m going to have to issue a formal apology to the Fruit of the Loom people for slandering them.

Sport Briefs

A shotgun wedding between “tightie-whities” and jock straps.  There’s a pouch in the front, a seat in the back and no fabric on a good part of the thighs.  Kinda sexy actually.

Boxer Briefs

They look okay, but like my hands underneath the table at dinner, they tend to ride up your leg and bunch up at the a–.  Try getting the ones with vents on the sides and it’ll cut down on the short-sheeting action.

Midway Briefs

The fabric goes way down your lap, preventing it from bunching up.  The fly has a padded opening which helps keep your periscope from surfacing without warning.  They look good and comfortable enough to wear around the house since they halfway look like shorts anyway.

Button Fly Boxer Briefs

I don’t like anything that prevents instant access to the goods.  They look and feel good, but who wants to waste time unbuttoning their underwear when you’ve got to p-ss like a fire hydrant?

Silk Boxers

Yes, oh God, yes!  It’s what I call “dating underwear.”  The high-quality silk is so soft and relaxing it feels like there’s nothing between your crotch and your date’s agenda.

Nylon Boxers

The fly is almost six inches down the front on many brands.  It’s also got a skimpy one-inch overlap.  Meaning, Willie will frequently and unexpectedly burst out like Ethel Merman flipping a window up and belting out “Everything’s coming up roses!”

Jock Straps

There’s only one jock strap that makes me wet:  The Go Softwear U.S. Army Jock.  The elastic band and pouch are dark green and black.  Plus the band is thicker than most, accentuating the cheeks in the most fuckalicious way.  The crowning touch is the U.S. Army stamp on the front of the pouch.  Trust me, it’ll make you salute.


I’m sorry, but only men who teach the blind should be allowed to wear this s–t.  That way the wearer won’t be laughed at and it’ll give the visually impaired a reason to be grateful for their blindness.


The straps cut into your flesh unless you wear them high above your hipbones.  But that puts extra tension on the rear string, making every move feel like somebody’s sandpapering your sphincter.  Try one of these a– strangulators on and you’ll be convinced that right wing fundamentalists are all wearing this s–t.  It would explain a lot, actually.  You’d hate everyone around you too if the crack of your a– was being waxed every time you reached for a Bible.  We’ve got to get these people to wear tightie-whities or we’re never going to win the fight for equality.