Holly Madison Says Many of Hugh Hefner’s Girlfriends Were Not Faithful to Him

The late Hugh Hefner was a magazine publisher who became a celebrity known for having multiple girlfriends at once. Even when he was well into his 80s, most of girlfriends were bombshells decades younger than him.

A lot of onlookers find Hefner’s “playboy” lifestyle intriguing, and one of his former girlfriends, Holly Madison, has let people in on the things that went on behind closed doors. According to Madison, many of Hefner’s girlfriends were not faithful to him.

Close up of Hugh Hefner and Holly Madison together
Hugh Hefner and Holly Madison | Victor Spinelli/WireImage

Holly Madison was Hugh Hefner’s ‘number one girlfriend’

Madison became Hefner’s girlfriend in 2001. At the time, she was 21 years old and he was 75. She recently shared on the podcast Call Her Daddy that part of the reason she decided to move into the Playboy Mansion as Hefner’s girlfriend was because she was struggling to make it as an actor in Hollywood.

She later became Hefner’s “number one girlfriend.” Madison also gained notoriety in 2005 when she appeared on E!’s reality show The Girls Next Door with two other girlfriends, Kendra Wilkinson and Bridget Marquardt.

In 2008, Madison and Hefner broke up. She also left the Girls Next Door series.

Holly Madison revealed many of Hugh Hefner’s girlfriends had ‘side boyfriends’

Hugh Hefner with his girlfriends in 2008, Holly Madison, Bridget Marquadt, and Kendra Wilkinson
(L-R): Holly Madison, Hugh Hefner, Bridget Marquardt, and Kendra Wilkinson | Lester Cohen/WireImage

RELATED: Holly Madison Once Revealed the Real Reason She Asked to Move in with Hugh Hefner – And It Had to Do with His ‘Bedtime Routine’

Madison shared with Call Her Daddy that, while Hefner did have a rule about his girlfriends not dating other people, many of them defied him anyway.

“When I first moved in, there were six other women living there, and a lot of them were dating other people on the side,” Madison said. “They weren’t supposed to. That was against the rule and Hef was super jealous.”

She revealed that some girlfriends would even tell Hefner they were going to visit their family as an excuse to spend time with their other boyfriend.

Madison also talked about this issue in her 2015 book, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.

She wrote, “How these ‘side boyfriends’ felt about their girlfriends dating Hugh Hefner, I don’t know. I imagine the girls weren’t forthcoming with these men and probably denied that they even had sex with Hef (they denied it to everyone). Most of them referred to ‘dating’ Hef as a big publicity stunt to help them launch their careers.”

Holly Madison compares her time with Hugh Hefner to having ‘Stockholm syndrome’

RELATED: ‘The Girls Next Door’: Hugh Hefner’s Reality Show Originally Had an Entirely Different Premise

Madison has talked extensively about her time in the Playboy Mansion, and a lot of the details paint Hefner in a negative light.

She told Call Her Daddy that, while she felt she was in love with Hefner at some point, it now feels like “a very Stockholm syndrome kind of thing.”

Additionally, Madison admitted her mental health was not in the best shape while she was Hefner’s girlfriend. She shared, “I think it was part of being nervous, partly doubting myself, partly being in this environment where I was always drinking and my mind was never stimulated. I was kind of always in fear of getting sabotaged by other women, getting kicked out, him yelling at me or embarrassing me in front of other people.”

After Madison left the Playboy Mansion, she began dating again. She was in a relationship with magician Criss Angel for a few months. Then, in 2013, she married businessman/film producer Pasquale Rotella. The couple has two children together, but they divorced in 2019.