Down the Rabbit Hole - Holly Madison

much mischief outside the walls before that hour. I had been present once when Vicky and Lisa had
rolled in a half hour past curfew and got a major dressing-down from Hef (no pun intended). He
kicked his feet, mustered up some questionable crocodile tears (was he really crying? I thought), and
told them that if they wanted to “stay out late” they could move out. Needless to say, his temper
tantrum made a lasting impression on me.
Next, the girlfriends were not allowed to “fraternize” with the staff unless absolutely necessary.
This rule was not to be taken lightly. Hef would totally lose it if he caught one of us talking with
anybody on the service team (and I eventually witnessed his irrational freak-out firsthand when future
girlfriend Kendra Wilkinson spent too much time in the butler’s pantry). According to mansion lore,
there were two instances of girls having relations with mansion staffers. First, his ex-wife allegedly
had an affair with one of the members of the security team—and Hef found out. Second, one of the
girlfriends had supposedly been caught sleeping with a butler. Now, I can’t prove that either of these
things happened, but it would explain why he was so overly sensitive about this particular rule. In the
beginning, I’m sure the staffers thought I was terribly aloof and cold, but I was honestly just scared
shitless. If I got kicked out, I had nowhere to go. I couldn’t risk it.
Each girlfriend was given a weekly “clothing allowance” of $1,000 for expenses. It was
expected that we use this money to purchase clothing to wear for evening events as well as beauty
treatments (hair, nails, waxing, etc.) that weren’t covered by his in-house account at José Eber Salon
in Beverly Hills. This was a welcome relief for me. It was clear that Hef preferred we dress in a
particular way when we were out on the town with him, and I was desperate to revamp my wardrobe
and fast! Hef made it abundantly clear that he preferred us in very over-the-top, sort of trashy outfits
(think BeDazzled rhinestone bustiers and skirts so short there was barely a point in wearing them).
When he would compliment a girl on a particular dress, pair of shoes, or even the way she wore her
hair, we all felt the need to replicate it for our next evening out.
The last major requirement was that girlfriends attend the events designated on Wednesdays,
Fridays, Saturdays, and Sundays. While the girlfriends were always eager to party at the hottest
Hollywood nightclubs on Wednesdays and Fridays, it was clear they used whatever excuse they
could to get out of “dinner and a movie” nights. Oftentimes, it would just be April and me flanking
Hef at the main dining table. We were still the two newest girls, so paying our dues was part of the
program. The other girls stayed out until 9 P.M. on the nose, not wanting to miss even a single minute
of freedom—which usually meant visiting the boyfriends that they kept on the side.
How these “side boyfriends” felt about their girlfriends dating Hugh Hefner, I don’t know. I
imagine the girls weren’t forthcoming with these men and probably denied that they even had sex with
Hef (they denied it to everyone). Most of them referred to “dating” Hef as a big publicity stunt to help
them launch their careers. Maybe some of the guys got a perverted little kick out of the fact that they
were dating the same girl as Hugh Hefner. Who knows?
Contrary to popular belief, most nights at the mansion were pretty boring. We usually ended up
in one of the bedrooms gossiping or watching TV. One night Lisa was hanging out in Vicky’s room
and the doors to our connecting bathrooms were open. When Tina came to visit, I went into Vicky’s
room to try and make an effort to be friendly with the girls. Tina was excitedly talking about her