Number One

After she moved into the house near Beverly Hills in LA, Madison and Hef swiftly bonded over a love of old movies, and her squeakyclean demeanour (as well as the no drugs rule, she didn’t date a ‘side boyfriend’ like others) soon saw her promoted to the coveted role of ‘girlfriend number one’, the chief courtesan in Hefner’s 21st-century harem. Hefner liked all the girls’ rooms to have pink walls and white carpets, and he paid for the girls to have plastic surgery (usually as a birthday present) and cars, but the favourite gift was a white gold diamond bunny pendant with a sapphire eye that each girl received when she became an official girlfriend. Madison, as girlfriend number one, was given a coveted yellow gold version. She also moved into Hefner’s master suite which takes up several rooms on the mansion’s second and third floors. “I don’t take relationships lightly, so I had to focus on Hef’s good qualities.”

“Um, his good qualities?” I ask. “They don’t exactly come through in the book.” In writing, Hef comes across as a controlling, paranoid and occasionally cruel character. She sighs. “His gentlemanly persona, his generosity to his friends, his sense of humour – I’d remind myself of these, and make excuses for the bad.” She called him ‘Puffin’, and nursed dreams of marrying him and having his children.

“Yes, I loved him. I was young and blinded by his fame and accomplishments. I’d never had much luck in love, so I convinced myself that guys my own age weren’t for me, that I was always meant to find Hef. Just like that, I was in love.”

Life at the mansion was creepily regimented for a supposed den of licentiousness and free love. Monday night was ‘Manly Night’, when Hef would invite his male friends over for dinner and a movie. Tuesday was ‘Family Night’, when Hef would see his ex-wife and their two sons. Wednesday and Friday night were ‘Club Nights’, when Holly and the others were expected to be ready for 10pm, for a night of clubbing in LA. Girlfriends had Thursday nights free (like Mondays and Tuesdays), but there was a strict 9pm curfew. “Apparently we couldn’t get into too much mischief outside the walls before that hour,” Madison notes, wryly. Saturday was a buffet and movie night with Hef, and Sundays were for the legendary ‘Fun in the Sun’ pool parties.

While the club nights were largely for show (“If there’s one thing Hef loves more than sex, it’s publicity” says Madison), the post-club orgy in his master bedroom was all too real. Her book is no tawdry tell-all, and she skims over the sexual nature of life in the mansion, so I have to ask: “Did you ever enjoy the sex?”

She pauses. “The sex was very routine, and something I don’t think any of the girls really enjoyed. We just wanted to get it over with. I just wasn’t into the group aspect. It was embarrassing, and it wasn’t something I would typically do in the bedroom.”

“Did Hef – this legendary ladies’ man – care about your sexual pleasure?”

“No, I don’t think he cared if we enjoyed sex. But I don’t think he cared about my happiness at all,” she says, firmly. “He cared about his own happiness, nothing more. And he believed that all a pretty young girl could possibly want from life was a little bit of money and a little bit of fame.”

“Didn’t you find this unbearably insulting and patronising?”

“Yes, of course. He was so old-fashioned and stuck in his ways. I don’t think he ever considered a woman’s selfrespect, or need to be surrounded by people who care for her. He was always puzzled when a girl left.”

From regimented routines to facing depression, ex-bunny Holly Madison on life in the Playboy Mansion