Former Playboy model and reality TV star Holly Madison has once again peeled back the curtain on her seven-year relationship with Playboy founder Hugh Hefner — and what she reveals paints a starkly different picture than the glamorous fantasy many imagined.
Madison, who dated Hefner from 2001 to 2008, recently appeared on In Your Dreams with Owen Thiele, where she candidly addressed common misconceptions about her sex life at the iconic Playboy Mansion.
While Hefner — the man behind the multimillion-dollar Playboy empire — built a reputation around luxury, parties, and sexual freedom, Madison says the reality was far less appealing.
“There’s a huge difference between being with him one-on-one and what went down during the group nights,” she said on the podcast. “When it was just the two of us, it was way more normal than people assume. But with others in the room? That was disgusting. I absolutely hated it — and I made sure everyone knew.”
Despite the 53-year age difference, Madison says the age gap itself wasn’t the main issue. “People always say weird stuff online like ‘old balls’ or whatever,” she laughed. “But honestly, that part never bothered me. Some people just love to make nasty comments.”
The more uncomfortable moments came not from Hefner’s age, but from the orchestrated sexual routines that took place behind closed doors. Madison has previously detailed these experiences on her Girls Next Level podcast, describing the mechanical nature of the group encounters.
“Hef would barely move,” she said. “It felt like this humiliating ritual you were forced into. You’d be lying there naked, doing something intimate while surrounded by other women who resented you, talked trash about you while it was happening. It felt like hell.”
Madison revealed that these encounters weren’t spontaneous — they were scheduled. “It was always the same days — Wednesdays and Fridays, right after going out to the club,” she told BuzzFeed News back in 2015. “It became this expected part of living at the mansion.”
For Madison, it all started to feel transactional. “We thought of it as a chore,” she said. “Something you had to endure if you wanted to keep your spot in the house. Everyone just wanted it to be over as fast as possible.”
Following Hefner’s death in 2017, more women have spoken up about the restrictive lifestyle inside the mansion — from bans on red lipstick to “one-way monogamy” rules where Hefner could see other women, but the girlfriends could not.
Madison’s insights continue to shift the narrative around one of pop culture’s most mythologized relationships — exposing the toll it took behind the glossy magazine covers and mansion walls.
