In her most recent podcast appearances throughout 2025, Holly Madison has continued to dismantle the carefully polished “fairytale” of the Playboy Mansion, offering a raw and often unsettling look at the power dynamics she navigated as Hugh Hefner’s “Number One” girlfriend. During an episode of the In Your Dreams with Owen Thiele podcast in May 2025, Madison, now 45, provided specific details about her intimate life with Hefner, aiming to clarify the misconceptions about their 53-year age gap while being brutally honest about the parts of the lifestyle she despised.
The Reality Behind the Bedroom Doors
Madison drew a sharp distinction between her private time with Hefner and the mandatory group activities that have become synonymous with the Mansion’s history.
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One-on-One Dynamics: Madison surprisingly described her private time with Hefner as “more normal than you would think,” noting that the age gap was not a significant factor in their physical chemistry.
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The Lights-Off Rule: She revealed that they always kept the lights off during intimacy, jokingly citing the proverb, “All cats are gray in the dark.”
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Group Expectations: In stark contrast, she labeled the group sex requirements—which occurred bi-weekly on a set schedule—as “disgusting.” She emphasized that she “hated it” and made her discomfort very clear at the time, though participation was essentially a “requirement” for living at the Mansion.
The “Nursery” Trays and Odd Rituals
Beyond the relationship itself, Madison shared bizarre details about the Mansion’s environment that painted a picture of a transactional and highly controlled world.
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Makeshift Lube Trays: Madison recalled seeing trays placed in almost every room—bathrooms, by the pool, and even on the tennis courts. These trays contained an odd assortment of items: Kleenex, Pepto Bismol, Vaseline, baby oil, and sunscreen.
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Hefner’s “Black Book”: She previously detailed a ledger Hefner kept to track which women had been intimate with him and when. This book was allegedly used as a tool of control; if a woman cited her period as a reason to abstain for too long, he would reportedly check the dates to catch them in a lie.
A Multifaceted Legacy
Despite her harrowing accounts of “Stockholm Syndrome” and the toxic competition between the women, Madison remains proud of her professional work within the Playboy brand.
| Aspect | Madison’s Current Perspective |
| Posing for the Magazine | 100% enjoyed it; she remains a fan of the artistic pictorials. |
| Working in the Studio | Described producing Playmate pictorials as a “super fun” and rewarding experience. |
| The Relationship | Viewed as a “cycle of gross things” marked by manipulation and emotional abuse. |
| Current Mission | Using her platform (including her Playboy Murders series) to expose the industry’s dark side. |
Today, Madison balances her past as a “Girl Next Door” with her current role as a true-crime executive producer and autism advocate, proving that she has moved far beyond the gates of the Mansion she once felt trapped within.
