7 Unhinged “Rules” Girlfriends Had To Follow At The Playboy Mansion

In the mid-late 2000s the reality show Girls Next Door was everything. It followed three women, Holly Madison, Bridget Marquardt and Kendra Wilkinson, who were “dating” Playboy founder Hugh Hefner and living in the Playboy mansion. From the outside, their lives looked enviable. Their day-to-day struggles consisted of finding cute outfits for Playboy parties, hanging out with other Playboy models, working out, swimming in the mansion’s famous pool and occasionally catering to their fussy octogenarian boyfriend.

Since the show ended, the reality behind the glamour has been revealed by Holly’s tell-all book and her subsequent podcast with Bridget, Girls Next Level. While there are some very serious Playboy misdeeds, like the trafficking hinted at in the A&E series Secrets of Playboy, the girls also discuss lighter behind-the-scenes drama and superficially icky factoids about Hef. For example, Hef had a lot of strict rules for his girlfriends which Holly detailed in her book. Some of the rules are controlling and others just show the boring reality of dating someone so old.

Here are seven of the rules Playboy girlfriends had to follow during the time Holly Madison was living at the mansion:

1. There was a 9pm curfew for the girls. On one occasion Holly witnessed two girls coming in 30 minutes late. Hef fake cried and threatened to put them on the street.
2. Hef’s girlfriends were told not to speak while Hef was being interviewed.
3. Girlfriends were not allowed to wear red lipstick or have French manicures.
4. The girlfriends were expected to stay within sight of Hef when they went clubbing. They could either sit with Hef or dance immediately in front of his table. They weren’t allowed to talk to other men.
5. Girlfriends were given a $1,000 weekly clothing allowance and allowed to use the house account at Jose Eber Salon in Beverly Hills. Saving the allowance or even using it for student loans was discouraged. The unwritten rule was that it was all supposed to be spent on their appearances and things that wouldn’t retain value if they decided to leave.
6. “Side boyfriends” were not allowed — though almost all the girlfriends had one. Holly says that she’s only sure she and Bridget Marquardt followed the rule faithfully. Mansion staff kept a book recording when the girls left the mansion and when they returned and Hef read it daily.
7. Everyone at the mansion adhered to a rigid weekly schedule because Hef, like all old people, was obsessed with routine. The schedule was:

• Fun-In-The-Sun Sundays: A pool party and screening a new release in the mansion’s movie theater.
• Manly-Night Mondays: Hef’s friends came over for dinner and cards.
• Family-Night Tuesdays: Hef’s ex-wife and sons came over. His sons were in high school during this time.
• Club-Night Wednesdays: Clubbing and the coming home for mandatory group intimate time with Hef.
• Off-Night Thursdays : No planned activities.
• Club-Night Fridays: A repeat of Wednesday’s activities.
• Movie-Night Saturdays: A buffet dinner and a screening of an old movie in the mansion theater.

Holly said many of the girls felt trapped at the Mansion. “Everyone thinks that infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in.”