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May 22, 2025 53 mins

#843. Holly Madison is here, speaking more of her truth — and did you know she has never signed an NDA!? No NDA = No Filter! In this unfiltered conversation, Kaitlyn sits down with the former Girls Next Door star to talk about everything from growing up a gifted bookworm in Alaska to racking up credit card debt chasing boobs, Hooters, and Hollywood dreams. Holly opens up about her undiagnosed autism, what really went down inside the Playboy Mansion, and the manipulative tactics that kept her there longer than she expected. From card tricks at Hooters to Hef’s infamous “grading system” for women, this one’s as jaw-dropping as it is personal.. Plus, an update on what Holly’s up to these days — and she is BUSY!

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EPISODE HIGHLIGHTS: 

  • (8:43) – Discussing going into credit card debt for breast augmentation!
  • (15:56) – Recounting her first encounter with Hugh Hefner and the events leading to her move into the Playboy Mansion.
  • (19:41) – Opening up about undiagnosed autism and how it affected her social interactions.
  • (29:54) – “I got dragged so hard during my book tour…”

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