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Holly Madison Claims Hugh Hefner 'Hated' Red Lipstick on Playmates, Wanted Them to Look 'Barely Legal'

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Sep. 12 2023, Published 3:36 p.m. ET

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Holly Madison continues to spill the tea about what went on behind the scenes at the Playboy mansion.

During the Girls Next Door star's appearance on the "Ahead of the Curve" podcast with Coco Mocoe, Madison claimed former boyfriend Hugh Hefner "hated" when playmates wore red lipstick — and the reason why is chilling.

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Holly Madison claimed Hugh Hefner did not like red lipstick on playmates because he wanted them to look 'barely legal.'

"When I was brand new, I wore red lipstick out a couple of times, and he didn't say anything about it. Because when you were the new girl in the group you were always treated well," explained the blonde beauty, who was 21 years old when she began dating the then 75-year-old media mogul.

"So I would wear red lipstick when I was new, and it wasn't a big deal," Madison recalled. "Until like six months into it, when I was living in his bedroom, and I was the main girlfriend, and he felt like he had the leeway to yell at me over it."

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Holly Madison was only 21 years old when she began dating Hugh Hefner at age 75.

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The former reality star went on to clarify that Hefner was not a fan of the ladies around him wearing the dark shade as he felt it made them look older. "I think he didn't love it because when he invented the concept of a playmate in the '50s, he wanted the women to look very young and fresh-faced because he felt like the look in the '50s at the time was very… He described it as 'somebody's older sister,'" she said.

"It was more sophisticated, fashion model, red lipstick," Madison noted of the late editor-in-chief of the magazine, whom she dated from 2001 until 2008. "It was a lot of fabric and big skirts and everything, and he hated that. He wanted skimpy and fresh-faced and very young looking."

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Holly Madison and Hugh Hefner dated from 2001 until 2008.

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"So I think that’s where his hatred of red lipstick came from," she added before bluntly admitting, "That was an older mature woman, and it wasn’t, like, the barely legal thing anymore."

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