Playboy model and former reality TV star Holly Madison is clearing the air about her infamous relationship with Hugh Hefner, and it’s not the grotesque tale some people expect.
Speaking on the In Your Dreams With Owen Thiele podcast, the 44-year-old opened up about what it was really like behind the closed doors of the Playboy Mansion, and it’s way more nuanced than the internet thinks.
“It Was More Normal Than You’d Expect”
Holly didn’t sugarcoat her experience, especially when it came to group encounters. She admitted that having sex in front of others at the mansion was something she “hated” and called it flat-out “disgusting.”
“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it,” she said.
But when it was just her and Hefner, she insists it felt surprisingly typical.
“If it was just me and him, it was a lot more normal than you would think.”
Not the “Old Balls” Scenario Everyone Assumes
One of the oddest parts of Holly’s post-Playboy fame has been the weirdly persistent trolling. Apparently, no matter what she posts, someone will still show up in the comments to joke about Hugh Hefner’s private parts.
“I feel like there was a time when I couldn’t post anything without some dumb*** in the comments like, ‘Oh, old balls,’ or something like that,” she said.
“But I’ve never seen such a thing. All cats are grey in the dark.”
In other words, she’s not feeding the cliché. While others may have tried to paint a horror story of her intimate life with an aging media mogul, she’s calling out the exaggeration.
The $3 Million “Bribe”?
Holly Madison also dropped a particularly strange, and kind of sad, detail about the end of her relationship with Hugh Hefner. After she broke up with him and started packing to leave the mansion, she found a folder sitting neatly on her side of the bed.
“This was very clearly for me to see,” she said. “So I look at it and it’s his will all printed out… He was leaving me $3 million.”
According to Holly, Hefner didn’t sit her down to talk about it, but rather placed the will where he knew she’d find it. It left her wondering whether it was a genuine parting gesture or a subtle attempt to get her to stay.
“It was kind of like a lowkey bribe but also sad because he can’t sit me down and talk to me about it.”
A Complicated Legacy
Holly Madison’s time in the mansion, from 2001 to 2009, was already dissected in TV shows like The Girls Next Door and in her bestselling memoir Down the Rabbit Hole. But this new interview adds even more layers to the narrative.
She’s not painting Hef as a monster, but she’s not romanticizing it either. Her candid take suggests that what happened inside the Playboy empire was a complex mix of power, discomfort, glamor, and sometimes, even something resembling normalcy.
