Life at the Playboy Mansion may have appeared glamorous from the outside, but behind closed doors, Hugh Hefner ran a tight ship with a surprisingly rigid daily routine for both his staff and live-in girlfriends.
In an article published by The Times before his death in 2017, the Playboy founder shared insights into his carefully structured lifestyle. Known for his nocturnal habits, Hefner revealed that his day typically began around 11 a.m. with breakfast in bed. Only then would he get up and change into what he called his “daytime” attire—silk pajamas.
“I wear flannel pyjamas at night, but it’s silk during the day and evening,” he explained.
Hefner lived at the mansion with several women he referred to as his girlfriends, including reality TV stars Kendra Wilkinson, Holly Madison, and Bridget Marquardt. In recent years, these former residents have spoken candidly about their time in the mansion, with Madison in particular shedding light on the darker aspects of life with Hefner—including what she has described as “disgusting” sexual encounters.
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’.
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)
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.
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’.
“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.
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.”