Twelve Absurd Boxer Shorts That Will Guarantee You Never Seal the Deal With a Woman

boxers main1

Guys spend 50% of their day trying to figure out how to get into a chick’s pants. The other 50% of the time is spent trying to figure out how to get a chick to get into our pants. So, why in the hell would anyone stack the odds against them by wearing absurdly stupid underwear? The last thing standing between her mouth and your junk, is a tiny (even tinier if you’re European) pair of shorts; so why let your drawers work against you, instead of with you?

For some unknown reason “novelty boxers” are a multi-billion dollar industry. Don’t be a part of it! Here are 12 boxers that will cock-block more than cock-sock.

Skid Marks

If you got them, don’t flaunt them. The only thing worse then the [skid] mark of the devil is the person who gave these boxers as a birthday gift. And besides, if you’re the type who would willingly put these on, people already assume you have skid marks in your boxers. Have no doubt about that. You just look like the type who doesn’t wipe properly. You don’t need to advertise it.

Choke Your Chicken

The only thing worse then a lame masturbation joke is feeling the need to print the obvious punchline over and over and over again. Trust me, if you are wearing these boxers, they’ll be plenty of chicken choking time.


Sure, your wife or girlfriend thought that branding your penis via underwear was a cute idea, but how are you supposed to have sex with a stranger if your penis fills them with guilt before it fills them? That said, we accept that these could be some sort of promotional item for the Liam Neeson movie of the same name. If that’s the case, these are even more disturbing than we initially thought.


People love buying underwear with penis size jokes on them. These people are dicks… big dicks. If you have a huge (black) or small (Asian) dong, don’t let your boxers give it away. Would people buy hot dogs if the label explained exactly what was inside?

Lost Remote

She already knows her biggest competition is the remote. No need to remind her of that as she yanks down your Levi’s for a mouth party. Also, your impending sex act now holds the very real possibility of reminding your woman that, instead of going down on your sweaty junk, she could be catching up on all of those episodes of Grey’s Anatomy on the DVR. This is a struggle for her attention that you will lose every time, Dr. NotDreamy.

Post-It Notes

POST-IT notes are a lot of things, but sexy isn’t one of them. Again, the 700 reminders on your drawers may just remind her that she could be doing something way more productive than, well, you. Also, no need to add anything else that’s sticky to your undies.

Bite Me

Women dig sweets. Chocolate and cookies to them is like pussy to us. But the word “BITE” is the last thing you want going through any women’s mind before she makes me her midnight snack.

Blast Pants

We trust there’s nothing that needs to be said here. Other than “no,” of course.

Some Hippie Bullshit

Hippies get a bad rap. They are hairy, smelly and kick around bean bags. Sound like anything else under your boxers? No need to turn your penis into a Phish concert.

The Man Girdle

Underwear should be as easy as possible to get off. No time to waste with buttons, zips, snaps or this ridiculous getup. I’m pretty sure these Man-Spanx have gotten as many guys laid as O’Doul’s.

A Touch of Class

Unless your dick was invited to a wedding without you, there is no need to go black-tie. Women hate feeling under-dressed. Unless she’s wearing her vagina ball gown, your fanciness will only make her self conscious about the suddenly less than elegant state of her own territory.


Cartoons on your boxers are always a gamble. Turning your penis into the nose of a beloved Disney character, is as good of an idea as taking life advise from a talking Cricket.

Secondhand Smoke is a column by Playboy Radio Morning Show host Kevin M. Klein. Follow Kevin on Twitter@TheKevinKlein.