Skip to content
Search AI Powered

Latest Stories

'Playgirl' Once Held A Contest Where The Winner Would Get To 'Sleep' With Donald Trump—And Yikes

'Playgirl' Once Held A Contest Where The Winner Would Get To 'Sleep' With Donald Trump—And Yikes
Seth Herald/Getty Images

In 1990, Playgirl magazine had a contest the prize for which was sleeping with Donald Trump.

Trump was married to Czech model Ivana Zelníčková until 1992.


If you've always wanted to sleep with the former Republican President, we regret to inform you that you missed your chance.

Anyway, lest you think this can't possibly be real, the internet obviously has screenshots, and hoo boy... they are something else.

Before you start saying this is a Photoshop job, it really did happen--Snopes verified the "Sleep With Donald Trump" contest and everything!

And like seemingly everything with Donald Trump, Snopes theorizes it was probably a publicity stunt orchestrated either by a book publisher or by Trump himself. Ever the showman, that guy.

In addition to the extremely sexy cover reading "Sleep With Donald Trump" (no thanks!), the Twitter post from the account Old Donald Trump posts included shots of the issue's table of contents and the contest page itself, both of which are... something!

The table of contents tries really hard to sell the reader on the idea of bedding "the Donald" with copy that naturally contains a typo. Incompetence has always been his brand, even in 1990!

@oldTrumpTweetz/Twitter

The table of contents reads:

"He’s rich, almost single and yours for the asking. Here’s how can you [sic] get the Donald out of your dreams and into your bed."

The phrase "almost single" is likely a reference to Trump's then-ongoing divorce from his first wife Ivana Trump, which made headlines at the time for her accusations of "cruel and inhuman treatment" by her soon-to-be ex-husband.

What a prize.

As for the contest page itself? Well... it has to be seen to be believed.

@oldTrumpTweetz/Instagram

It's hard to land on the most bonkers thing here. Is it the choice of a sexy lady to pitch this contest to straight women and gay men? Is it the phrase, "YES, I want to sleep with Donald Trump!" on the entry form? Or is it the crass dig at Ivana Trump?

Who's to say, but fittingly for Donald Trump the whole thing turns out to have been a cleverly worded ploy--the prize wasn't a date with Trump but rather a copy of a book about him and a pillowcase with his face on it, so you could "lie there whispering sweet nothings in his ear all night."

If you're screaming in horror, you're not alone--lots of people on Twitter were horrified.






And of course there was wave after wave of jokes.





If any of the winners of this contest are reading this, please, please get in touch. We need to see those pillowcases!

More from People/donald-trump

Jeff Ross
Mike Coppola/Variety via Getty Images

Comedian Jeff Ross Shares Photos Of Puffed Up Lip After Allergic Reaction To Ice Cream

Insult comic Jeff Ross revealed he had a medical emergency after a show Saturday night that resulted in a trip to the ER. However, he assured fans the show must go on despite "looking like Mickey Rourke at the end of The Wrestler."

Ross recounted the ordeal on Instagram, showing his swollen lip taking over his face from eating burrata ice cream after his Take a Banana for the Ride show in Mill Valley, California, near San Francisco.

Keep ReadingShow less
screenshot of Jesse Watters on Fox News
Fox News

Jesse Watters Offers Mind-Numbing New Claim About Masculinity—And Is Instantly Dragged

Problematic Fox News MAGA pundit Jesse Watters has made another bizarre claim about masculinity.

Having already taken exception with eating ice cream, drinking milkshakes, and taking bubble baths, Watters is now targeting tech jobs.

Keep ReadingShow less
Donald Trump with the Dodgers
Kevin Dietsch/Getty Images

Trump Leaves Everyone Confused With Hilariously Bizarre Word Salad Tribute To The Dodgers

President Donald Trump was widely mocked after he welcomed the 2024 World Series-winning Los Angeles Dodgers to the White House on Monday with a bizarre, tangential, and rambling speech.

The team arrived at the White House on Monday morning, where Trump, in his remarks, praised two-way star Shohei Ohtani and infielder Mookie Betts. The Dodgers had defeated the New York Yankees in five games to clinch their second World Series title in five seasons.

Keep ReadingShow less
Donald Trump
Kevin Dietsch/Getty Images

Trump Roasted After Giving Clunky New Nickname To People Criticizing His Tariffs

President Donald Trump was criticized after he pushed back against critics of his tariffs, coming up with a new nickname for the "weak and stupid" people who oppose them.

The Trump administration’s newly imposed tariffs on imports from various countries have unsettled consumers, triggered a trade war, disrupted global markets, and sparked widespread fears of a potential recession in the U.S. and beyond.

Keep ReadingShow less

Childhood Experiences People Thought Were 'Normal' But Weren't At All

Content Warning: Child neglect, child abuse, narcissism, gaslighting, people-pleasing, and other traumatic childhood experiences

It's important for us to work on ourselves, to continue bettering ourselves throughout our limited time on this earth, and a key way of doing that is acknowledging what we do not know, and working on that.

Keep ReadingShow less