I Simply Must Know Who Won This 90s ‘Playgirl’ Competition To “Sleep With Donald Trump”

I’m very sorry that there is nothing good about what I’m about to show you. Back in the 90s it seems Donald Trump was a considerable heartthrob – so much so that an issue of Playgirl in 1990 had a competition running where 25 lucky winners would get Big Don himself in bed with them.

Uncovered by Yvette d’Entremont and gleefully posted on her Twitter, the competition was so much of a pull that it was used (somewhat clickbaity) on the cover of the magazine simply by slapping a big SLEEP WITH DONALD TRUMP on the front, right underneath 69 THINGS TO DO WITH YOUR TONGUE. Nice.

The actual write up of the competition itself reads like Donald wrote it himself, really. Considering it starts with “He’s tall, good-looking, about to be divorced, and rich beyond your wildest imagination” it’s absolutely penned by someone who’s either got mad tickets on himself (G’day Donnie) or actually wants to be the next Mrs Trump after he was apparently about to divorce from Ivana.

Seriously, wrap your eyes around this pearler.



Donald Trump Playgirl
OK Playgirl I’m going to need you to reveal your sources on that “reported woman”.

Ok so full disclosure, this actually meant that the 25 (!) winners got a pillowcase with Donald Trump’s face on it, so they could snuggle up to the future President Of The United States in the privacy of their own homes. Which, to me, is a deeply cursed thing.

Like imagine bringing someone back to your house for a cheeky hookup and there’s a young Donald Trump face just looking back at you from the bed. God, imagine even just trying to SLEEP with that mug staring at you. I’m not too sure how nightmares work but I feel like this would be the perfect fuel for it.

Actually, I’d really like to know if anyone still has their pillowcase, because I would like to 1. take it and 2. fling it into the sun immediately.

I simply cannot think of anything worse than a Donald Trump waifu pillow. Jesus fucken wept.