Jackass Presents: Bad Grandpa at the Playboy Mansion
Find out what happens when Bad Grandpa Irving Zisman crashes the Playboy Mansion.
How To Succeed At Picking Up Women (And Fail At Keeping Them Around)
Pulled from our best (and worst) dating experiences, we created a game plan for all the V-day singles hoping to get lucky.
#AskPlayboy: Jenny Mollen on Cleavage Optimization
Jenny Mollen answers one guys quest to utilize his girlfriend's boobs to their best potential in the sack.
#AskPlayboy: Jenny Mollen on Sex Toys
Move over Fifty Shades of Grey, there's a new sheriff in town. Jenny Mollen tells one guy what he needs to do about his girlfriend's...
Francofile: Talking with Mila Kunis
What’s it like being the world’s sexiest woman? JAMES FRANCO asks his close friend.
#AskPlayboy: Jenny Mollen on Bad Lingerie
How do you break it to your girlfriend that her lingerie sucks? Jenny Mollen answers.
#AskPlayboy: Jenny Mollen on Facebook Snooping
Jenny Mollen weighs in on girlfriends who snoop their boyfriend's Facebook accounts.
Hot Girls Get Away with Shit: Special Delivery with Playmate Nikki Leigh
What would you do if Playmate Nikki Leigh answered the door in only a bikini? Yeah, we thought so.
Gifts For Her That Benefit You
It's okay to be selfish sometimes. And sometimes that time is Valentine's Day. Please yourself while pleasing her. Love is give...
The Evolution Of Hotness
Women are getting hotter, and guys have always been left in the dust. Find out what methods we've used to keep our cool in the...
How Porn Changed Technology
Ever wondered how Porn has aided in technological advances throughout the years? Read on!
Unlock Exclusive THIS IS THE END Footage
Check out hilarious videos from the cast of This Is The End!
Hot Girls Get Away with Shit: Take the Shirt Off Your Back with Playmates Amanda Cerny and Nikki Leigh
Playmates Amanda Cerny and Nikki Leigh are out to get you topless.
Hot Girls Get Away with Shit: Sexy Psychic Prank with Jaclyn Swedberg
Would you fall for this trick played by Playmate of the Year Jacklyn Swedberg? We predict you would.
Does the enemy wear Underoos?
The Good, the bad and the ugly of MILF dating.
Hot Girls Get Away with Shit: 3 Prank Dates With A Playmate Feat. Jaclyn Swedberg
Think winning a date with Playmate of the Year Jaclyn Swedberg would be the best date ever?
Hot Girls Get Away with Shit: Horrible Bake Sale with Playmate Nikki Leigh
What would you do if Playmate Nikki Leigh told you she was raising money for breast implants?
The Best Valentine's Day Advice You Ever Got
When all is said and done, it;s the simple things, not the grand gestures that usually prove the most fruitful.