NEWSHolly Madison Says She 'Fell' for Hugh Hefner 'Right Away' in Resurfaced Interview: 'I Was in Awe of Him'

Holly Madison opened up about falling for Hugh Hefner 'right away' when she was 21 years old.
June 23 2026, Published 7:29 a.m. ET
Holly Madison is looking back on the beginning of her relationship with Hugh Hefner.
During a resurfaced episode of Keke Palmer’s podcast, “Baby, This is Keke Palmer,” the former Bunny opened up about what initially drew her to the Playboy founder when she was just 21 years old. Hefner was 75 at the time.

Holly Madison revealed she was immediately drawn to Hugh Hefner after meeting him at a Playboy event when she was 21 years old.
According to Madison, she became interested in Playboy because “there were so many women who had been playmates and were famous in the ‘90s,” like Anna Nicole Smith and Pamela Anderson.
“I wanted to be in the magazine. I got invited to a Playboy party. I was working as a Hawaiian Tropic model at an event, and Hef's doctor came and said, ‘I want to invite all these girls to the next party.’ I was in awe of him. I thought he was this amazing person who had created so much and done so much. I fell for him right away,” Madison recalled, adding that Hefner “seemed like a gentleman and so interesting.”
How Madison Became One of Hefner’s Girlfriends

Holly Madison said her admiration for famous Playboy Playmates like Anna Nicole Smith and Pamela Anderson first sparked her interest in the brand.
Madison also detailed the unexpected chain of events that eventually led her to move into the Playboy Mansion and become one of Hefner’s girlfriends.
She shared, “I was invited to go out with him and the girls one night cos they would go out to clubs a couple of times a week, and he had multiple girlfriends at the time, and I knew what that meant. And even though I really liked him. I wasn't into doing that until one day I didn't have anywhere to live. So, I was like, I should give this I should give this a try. I was at a pool party, and one of the bartenders said, oh, one of the girlfriends just moved out. There's a new spot. And I thought, you know what? I'm going to do this crazy.”
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‘It Was Both’

Holly Madison admitted that becoming one of Hugh Hefner’s girlfriends was influenced by both ‘love and survival.’
Palmer later asked Madison whether her decision was driven by romance or necessity.
She then answered, “It was both; I knew I really liked him in the beginning, wouldn’t say love because I did not know him that well. But it turned into that quite quickly. We bonded really quickly. I was always the one who was by his side for all the dinners and movies.”
Despite developing strong feelings for Hefner, Madison acknowledged that there were parts of the arrangement that were difficult for her to accept.
“I did not like the fact that there were multiple partners in the relationship for so long, but other than that, I was young, and I would not feel this way now. But I felt very much in love for sure,” Madison added.
'Walking on Eggshells'

The reality star described life at the Playboy Mansion as stressful and said she constantly feared being asked to leave.
While Madison has spoken in the past about her affection for Hefner, she has also been candid about the challenges she faced while living at the Playboy Mansion.
In a more recent interview, the blonde babe described the atmosphere as "walking on eggshells" and recalled having to follow a strict 9 p.m. curfew.
"As a young woman who was struggling even before I moved in. I was like 'Woah, what would I do if that happened to me?'" she remembered of possibly being booted. "Because not only would I be a broke college student again, but I would also have the stigma of everyone knowing I lived here."


