Inside Holly Madison’s ‘Cycle of Misery’ During Hugh Hefner Relationship

Holly Madison might be best known these days as a social media influencer and bestselling author but she was first introduced to the world as Hugh Hefner’s girlfriend. As one of the stars of the hit early 2000s TV show The Girls Next Door, Madison became a fan favorite, with fans loving her sense of humor and retro sense of style. Still, there was more going on behind the scenes than what met the eye, and in a brand-new docuseries, Madison is opening up about life at the Playboy Mansion, and the reality of her relationship with Hefner

When did Holly Madison start to date Hugh Hefner?

Madison had big dreams as a young girl and worked as a model when she was still in her teens. Madison had ambitions of fame and fortune, and when she was 20, she crossed paths with Playboy founder, Hefner. She quickly gained Hefner’s favor, and after about a year of dating, Madison moved into the Playboy Mansion, becoming one of Hefner’s “main” girlfriends. 

In 2003, Madison became a star after the reality TV series The Girls Next Door debuted. The show chronicled the lives of the three women who were dating Hefner at the time, including Madison, Kendra Wilkinson, and Bridget Marquardt. The show was a hit and did a lot to glamorize the idea of life inside the Playboy Mansion. However, things weren’t as glamorous as they appeared – and in 2008, Madison broke up with Hefner. She moved out of the Playboy Mansion not long after.

What did Holly Madison say about her ‘cycle of misery’ dating Hugh Hefner?

Holly Madison
Holly Madison | Ethan Miller/Getty Images for MGM Resorts International

In the years since ending her association with the world of Playboy, Madison has talked openly about how toxic her relationship with Hefner truly was—and what she has learned in retrospect. In a brand-new docuseries, “Secrets of Playboy,” Madison talked about the unhealthy cycle that she was stuck in.

As reported by Insider, Madison said “There was a point where I felt really low. Like I didn’t feel like I had any options. There was a point in time, a couple years in, after we had gone out, and after we had all been in the bedroom, everybody was leaving and walking out, and I was in the bathtub, and I just wanted to drown myself.”

Madison went on to say “I just felt like I was in this cycle of misery. And those feelings would never last long, but you have those moments, like, ‘What did I gain from this experience?'”

Holly Madison has been open about her negative experiences at the Playboy Mansion

Through it all, even at her lowest points, Madison maintained that she tried to hold onto the idea that “something” would come out of her experiences at the Playboy Mansion. Later on in the interview for the docuseries, Madison talked about Hefner’s controlling ways, revealing that she, along with Hefner’s other girlfriends, were expected to follow a strict curfew and “weren’t really allowed to leave” unless it was for a big holiday.

After leaving Hefner in 2008, Madison worked hard to build her career on her own terms. She’s successfully carved out her own identity, working as a model, showgirl, writer, and influencer – all while making it clear that she’s never forgotten where came from. Madison’s own transparency about the hard times at the Playboy Mansion has done a great deal to shed new light on the mysterious Playboy empire, where nothing is quite as it seems. 

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