The Playboy Mansion has long been seen as glamorous and carefree, but much of its reality stayed hidden from the public. Only those who lived there during Hugh Hefner’s lifetime truly understood what daily life was like behind the gates.

Holly Madison, now 45, recently reflected on that period while appearing on a podcast hosted by Owen Thiele. She spoke openly about her years living at the mansion and shared a more complicated picture than the fantasy often portrayed.

Madison was in a relationship with Hefner from 2001 to 2008, placing her at the center of mansion life. She explained that her private, one-on-one interactions with him felt far more normal than people assume, while group situations were a very different experience.

She made it clear that she disliked those group encounters and said she voiced her discomfort at the time. According to Madison, pressure and power dynamics played a major role in shaping her experience, even as the public focused heavily on the 53-year age gap between her and Hefner.

Beyond relationships, she described the mansion’s everyday atmosphere as strange and unconventional, noting that the environment itself often felt unsettling. She summed it up in one word: “weird.” Despite the challenges, Madison said she does not regret her professional work with Playboy, enjoyed posing for the magazine, and views that chapter of her life as a mix of opportunity, discomfort, ambition, and personal growth.