These Are Apparently The "Worst" Things About Dating Hugh Hefner In Holly Madison's New Book


E! – In her recently released memoir, Down the Rabbit Hole, the Playboy founder’s former girlfriend, Holly Madison, made several claims about Hefner’s behavior during her time in the famed Playboy Mansion. Excerpts from the book made headlines, and on Monday, Hefner finally addressed Madison’s allegations.

“Over the course of my life I’ve had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives, and I’m pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight,” he tells E! News in a statement. “I guess, as the old saying goes: You can’t win ‘em all!”

“The stories in the book speak for themselves,” Madison told E! News in a statement Monday. Per Hefner, they have not spoken to each other in four years.


Hugh Hefner’s former “girlfriend” Holly Madison released a new tell-all book and some of the snippets are going viral because of how crazy some of the findings they are (I guess it previously seemed like a much normal situation of an octogenarian banging out his 20 year old employees before the book came out). The chick sites are all riled up about it and Cosmo did a takedown of “the 14 worst things about Hugh Hefner” from the book that I thought was interesting…it’s worth a read to see them all but here are the ones I found the most ridiculous.


1. Though they publicly denied it, all girlfriends were expected to participate in Hef’s bizarre bedtime group sex ritual. “I didn’t immediately realize that all girlfriends were required to sleep with Hef,” Madison writes.


This seems just like a communication issue. Before getting in on this, Holly Madison wasn’t really about that life and thought it was just fun and games for publicity and a reality show. Instead, she had to get taffy balls on her chin and pretend to like every minute. But she never actually avoided doing it at the time so I don’t really have much sympathy here? It’s a thin line between prostitution and pseudofame, Holly.



3. Hef offered Madison a quaalude out of a crumpled tissue on her first night out clubbing with him. When Madison told him she doesn’t do drugs, she says Hef replied, “Usually I don’t approve of drugs, but you know, in the ’70s they used to call these pills ‘thigh openers.'”


When you’re dating a grandpa, you get grandpa shit. That means two things: 1) Getting used to having to pretend to enjoy old man beef jerky pipe and 2) Looking the other way when Hef drops wildly inappropriate things that most people wouldn’t say these days like “thigh opener” or a wide variety of colorful racial epithets. If anything, she should have appreciated the history lesson as a reminder that hey, it could be worse.


4. Among his bizarre set of mansion rules, Madison writes, were that the girlfriends change into identical flannel pajamas before the bedtime routine.


Hef seems like a homogenized dude given that all his chicks are white, blonde, and plastic so having them all wear the same thing seems not surprising. But flannel? Weird move. I mean it’s more comfortable than having them wear garters like a Victorian hooker all the time but I just don’t get how it’d be sexy for Hef to see a group of chicks in “I’m a married mom who’s given up on life” pajamas. If we’re going to have a weird sister wives deal at least demand they wear booty shorts.


6. He made his sons Marston, 9 years old when Madison moved in, and Cooper, 10, share a bedroom with a girlfriend. This was Bedroom 3, which came with three beds and a private bath. “Though they never stayed over when I was there, there were still toys scattered across the bedroom floor,” Madison writes, “which made for an incredibly odd and, frankly, creepy juxtaposition.”


Okay yes it’s very weird to have your young sons’ toys in a room with your harem. But if Cooper and Marston stay over? A wealth of spank bank material, enough to get them to 9th grade. That’s genuinely the nicest thing I’ve ever heard a father do for a son (that’s also incredibly creepy and weird for the girls, but let’s focus on the positives here).


8. Hef demanded his girlfriends be in by the 9 o’clock curfew each night. When Madison witnessed two of the girlfriends come in past 9 one night, Madison writes, Hef “kicked his feet, mustered up some questionable crocodile tears (was he really crying? I thought), and told them if they wanted to ‘stay out late’ they could move out.”


Wait you’re telling me the rich geriatric guy who contractually locks up chicks to fuck him and make him look cool is secretly very insecure and goes to bed at a normal time for an 80-year-old man? Shocker. Plus he’s old as fuck, testosterone dips, of course he’s got full on waterworks going when they make him feel like the weird old man he is, as soft as his very tasteful smoking jackets.


13. He once told [Kendra] Wilkinson she looked like she was “putting on some weight,” and warned her to watch her diet.


Everything so far indicates that this is the very definition of a transactional relationship. If you’re not living up to your half of the transaction, you have to fix it or you’re in breach. Looks like Holly didn’t pay much attention in contracts class when she went to law school.


14. He keeps a picture of every girl who’s ever been to the mansion. A mansion staffer would take photographs of women visiting for the first time, Madison says. The photos (mostly Polaroids) were saved for Hef to review the next day. “He would label them A, B, or C (based primarily on their looks but also on how scantily clad they were) before having them catalogued in his social secretary’s office,” Madison explains. Madison would eventually discover she received an “A.”



I suppose fundamentally this is kind of shitty but at the same time I’d absolutely KILL to see this book of photos so I’m in no place to judge. Plus complaining about this when you got an A in the book is very patronizing to the poor Bs and Cs of the Playboy Mansion.


Anyway the whole article is here if you want to read it, there’s other fun stuff about Hef having to get high and jerk himself to get off and his standing offer to buy all his women boob jobs. Highly recommended (and might somehow make you appreciate what a once in a lifetime creep Hef is even more).


(Holly Madison/Hugh Hefner photo by s_bukley/Shutterstock)