Playboy's Holly Madison Blames 'Stockholm Syndrome' for Making the 'Bad Decision' to Date 'Master Manipulator' Hugh Hefner

Former Playboy bunny Holly Madison opened up about the “bad decision” she made to date Hugh Hefner. Though the founder of Playboy Magazine died at the age of 91 in 2017, Madison made it clear in a new interview that she wished she had never experienced her time with Hefner.

“It felt dangerous to me, even then, even to the point of when I moved into the Playboy mansion,” she detailed of living in Hef’s mansion while she dated him from 2001 to 2008.

“Even though there were a lot of things going on that were way out of my head, I felt like that seemed like kind of a safer, you know, corporate, whitewash type of thing than just, you’re walking downtown running your errands, and you have people approaching you in the street trying to get you into escorting or whatever. It just felt very shady,” she said.

Madison stated she felt “there was a cult mentality with a lot of the people who surrounded Hef,” adding, “They just kind of look at him as not human and infallible. And you can’t even say something bad adjacent about him without being excommunicated. You look at some of the signs of what makes a cult, and I could definitely apply them to the Playboy world for sure.”

Though Madison admitted she “didn’t know him well,” she realized after her time in the mansion that she “had this mindset of being in love, and it was kind of tinged with a little bit of Stockholm syndrome,” which kept her associated with Hefner and his world.

She continued, “I thought I was connecting with somebody when really, I was just somebody who had trouble connecting with people my whole life, and I met somebody who was a master manipulator.”

“So I look back and I just see somebody who was young and impressionable,” Madison shared. “Just kind of in a fog, almost. I think the fog was more just having such a warped mindset, cognitive dissonance, thinking I’m in love with somebody and realizing I got in way over my head… but always trying to justify that.”

Madison noted how those who lived in the Playboy mansion were seen as only a “s-- symbol” and were “written off by the media.” She said that although “it affected my reputation,” she was able to “turn lemons into lemonade” with reality shows and “side hustles.”

Though she said "it was a very confusing time [for] me,” Madison has since moved past her complicated relationship with the late Hefner. She now hosts The Playboy Murders, a true crime series about murders related to Playboy personnel. Season 3 will be released on May 5 on Max.

Madison spoke with The New York Post about her experience with Hefner.