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Bizarre weekly schedule Hugh Hefner had at Playboy mansion as ex-girlfriend Holly Madison details 'disgusting' sex act

Home> Celebrity

Updated 09:43 7 May 2025 GMT+1Published 09:34 7 May 2025 GMT+1

Bizarre weekly schedule Hugh Hefner had at Playboy mansion as ex-girlfriend Holly Madison details 'disgusting' sex act

The Playboy magazine founder made clear he was a man of routine

Emily Brown

Emily Brown

Featured Image Credit: Getty Images/Michael Bezjian

Topics: Hugh Hefner, Sex and Relationships, Celebrity

Emily Brown
Emily Brown

Emily Brown is UNILAD Editorial Lead at LADbible Group. She first began delivering news when she was just 11 years old - with a paper route - before graduating with a BA Hons in English Language in the Media from Lancaster University. Emily joined UNILAD in 2018 to cover breaking news, trending stories and longer form features. She went on to become Community Desk Lead, commissioning and writing human interest stories from across the globe, before moving to the role of Editorial Lead. Emily now works alongside the UNILAD Editor to ensure the page delivers accurate, interesting and high quality content.

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Life at the Playboy mansion might have looked like all fun and games from the outside, but Hugh Hefner actually had a strict schedule for his staff and girlfriends to abide by each day of the week.

In an article published for The Times prior to his 2017 death, Hefner detailed his 'day in the life' and made clear that he was a man of routine.

The founder of Playboy described himself as a night owl, explaining his day began around 11am with breakfast in bed, after which he got up and 'put on [his] pyjamas for the day'.

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"I wear flannel pyjamas at night, but it's silk during the day and evening," he said.

Hefner lived at the Playboy mansion with a series of women who were his girlfriends, including reality TV stars Kendra Wilkinson, Holly Madison and Bridget Marquardt, all of whom have since opened up about their experiences in the mansion.

Hefner lived in the mansion with a series of girlfriends (Michael Bezjian/WireImage)
Hefner lived in the mansion with a series of girlfriends (Michael Bezjian/WireImage)

Each day of the week, the girlfriends could expect Hefner to have certain plans which they could be expected to take part in.

Monday

Hefner kicked off the week with what was dubbed 'Manly Night', when he invited 'the guys', who Hefner described in The Times as 'old friends', over for dinner and screened a classic movie in his screening room.

Tuesday

In his 'day in the life' article, Hefner explained that Tuesdays were dedicated to 'taking the girls out to dinner'.

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He allowed his girlfriends to 'pick the restaurant' and 'pick from the menu', but Hefner organized his own food.

He explained: "I have lamb chops and a baked potato sent in from the mansion, so mine is set. The three girls - the last of them, Kendra, joined us about three years ago - and I spend a lot of time together, but most of my free time is spent with Holly."

Hefner stuck to routine throughout the week (Charley Gallay/Getty Images for Playboy)
Hefner stuck to routine throughout the week (Charley Gallay/Getty Images for Playboy)

Wednesday

According to a weekly breakdown laid out in GQ, Hefner's Wednesday nights were dedicated to clubbing, when the girlfriends were prepared by 10pm to go out for the night in LA.

Thursday

The women reportedly had a night off on Thursdays, though they still had a 9pm curfew to abide by.

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Hefner explained: "Most nights we're up in bed by 10 or 11, but we watch a movie or something and Holly will usually fall asleep before I do."

Friday

In true weekend fashion, Friday night was another Club Night for the mansion occupants to hit the town - though in writing for The Times, Hefner admitted that while he 'still liked' big parties, he didn't enjoy them 'as much as [he] used to'.

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"The best times for me are the quiet times, and the best time of all is, you know… in bed with Holly," he said.

Saturday

On Saturday, Hefner hosted a buffet dinner and another movie night with his girlfriends.

Sunday

And finally, the Playboy founder rounded off the week with a so-called 'Fun in the Sun' pool party, followed by dinner and an evening movie.

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Hefner hosted regular parties at the mansion (James Aylott/Getty Images)
Hefner hosted regular parties at the mansion (James Aylott/Getty Images)

Hefner described Holly as being as 'close as [he'd] come' to having a 'soul mate', but the former girlfriend has since admitted that there were things she didn't like about her relationship with Hefner.

Speaking on the In Your Dreams Podcast with Owen Thiele, Holly described having sex with Hefner along with his other girlfriends at the time, compared to when they were alone together.

She said: “Well, it's a very different story between when we were just by ourselves than with everybody else in the room. Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it. If it was just me and him, it was a lot more normal than you would think.”

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