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Hugh Hefner's ex-girlfriend Holly Madison details relationship and explains why she didn’t really 'know him'

Home> Celebrity> News

Updated 18:01 4 May 2025 GMT+1Published 14:22 4 May 2025 GMT+1

Hugh Hefner's ex-girlfriend Holly Madison details relationship and explains why she didn’t really 'know him'

Holly Madison branded Hugh Hefner a 'master manipulator'

Poppy Bilderbeck

Poppy Bilderbeck

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Featured Image Credit: Mathew Imaging/FilmMagic via Getty Images

Topics: Celebrity, Hugh Hefner, Mental Health, Sex and Relationships

Poppy Bilderbeck
Poppy Bilderbeck

Poppy Bilderbeck is a freelance journalist with words in Daily Express, Cosmopolitan UK, LADbible, UNILAD and Tyla. She is a former Senior Journalist at LADbible Group. She graduated from The University of Manchester in 2021 with a First in English Literature and Drama, where alongside her studies she was Editor-in-Chief of The Tab Manchester. Poppy is most comfortable when chatting about all things mental health, is proving a drama degree is far from useless by watching and reviewing as many TV shows and films as possible.

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Holly Madison has opened up about the 'fishbowl' life of living in Hugh Hefner's Playboy Mansion and how her mindset ended up 'warped'.

Madison dated Hefner from 2001 to 2008, and was even named as his 'number one girlfriend' on reality TV show The Girls Next Door.

However, since the Playboy publisher passed away in 2017 at the age of 91, Madison - among other Playmates - have come forward to reveal certain realities of what he was like alongside what it was like living in the infamous Playboy Mansion.

Madison has previously reflected on the difficulties of living life in the 'fast lane' alongside why the mansion felt like a 'cult' and lifted the lid on her and Hefner's sexual relationships, including certain 'disgusting' elements but also one stereotype she often found discussed online which was far from the truth.

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However, she's since opened up about not just the physical aspects of her relationship with Hefner, but mental too, realizing with hindsight she 'thought' she was 'connecting' with him but actually 'didn't know him well'.

The 45-year-old told the New York Post: "I had this mindset of being in love, and it was kind of tinged with a little bit of Stockholm syndrome.

"I thought I was connecting with [Hefner], when really I was just somebody who had trouble connecting with people my whole life. And I’d met somebody who was like a master manipulator."

Looking back, Madison sees herself as 'somebody who was young and impressionable and just kind of in a fog almost'.

And even further than being in a 'fog', Madison notes she now thinks her mindset at the time of her relationship with Hefner was actually 'warped' and she was exhibiting 'cognitive dissonance'.

Holly Madison said she needed perspective (Mark Sullivan/WireImage)
Holly Madison said she needed perspective (Mark Sullivan/WireImage)

Madison explained she may've initially thought she was 'in love' but did soon realize she 'made a bad decision' but ultimately was so 'in over [her] head' she just had to try and 'justify' it.

She also reflected on how being at the Playboy Mansion affected not only 'part' of her life but also her 'reputation' which meant she then had to figure out how to 'make it okay' once on the outside of it all.

Though Madison noted that she was 'lucky' to be able to 'turn lemons into lemonade, with things like the reality show, and other side hustles'.

She resolved: "You know, when you’re in the goldfish bowl, everything looks all blurry and distorted. And you don’t see things clearly until you’re outside of the goldfish bowl."

  • Widow of Hugh Hefner reveals 'five-step seduction method' the Playboy boss would often use
  • Hugh Hefner's ex-girlfriend Holly Madison reveals 'disgusting' sex act she 'hated' doing with the late mogul
  • Hugh Hefner's ex-girlfriend Holly Madison says living in Playboy Mansion was like a 'cult'
  • Hugh Hefner's ex-girlfriend Kendra Wilkinson reveals damaging impact their relationship has had on her sex life

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