Down the Rabbit Hole - Holly Madison

either. I knew that the role of girlfriend was coveted by many and fleeting for some, so I expected the
women to be defensive, protective, and, quite frankly, bitchy—especially this crop of girls who
looked more like garden variety strippers than dazzling Playboy bunnies. I was surprised with how
wrong I thought I was. They were accepting and encouraging—some more than others—and Vicky,
one of the more seasoned girlfriends, even offered to take me under her wing as I navigated this new,
foreign world. It really didn’t occur to me that they had their own agenda, which I would soon learn.
The girls would rattle on about how glamorous it was being a “girlfriend” and how every girl
that moved into the mansion would eventually become a Playmate; they all had a weekly allowance to
buy club clothes and get their hair and nails done; and the afternoons free to spend however they like.
As a girlfriend, you just needed to be available on the nights when Hef hosted events at the mansion,
went clubbing in Hollywood, attended red carpet parties, etc.
This may sound naïve, but I didn’t immediately realize that they were actually required to sleep
with Hef. Back then, none of the girlfriends talked about it. When I inquired about the more intimate
duties, Vicky fiercely denied that anything sexual went on with Hef.
“It’s all for show,” Vicky said, explaining that the whole thing was basically a Hef-orchestrated
publicity stunt.
The girlfriends were simply dazzling arm candy to help keep up his Playboy image. It sounded
more like a job than an actual relationship—and they sold it to me so matter-of-factly I was able to
overlook what this “job” really sounded like. Hef’s former girlfriend Katie Lohmann had recently
left, and Vicky told me that when she went on Howard Stern after scoring her centerfold and
cheerfully denied that any of the girls slept with Hef with a dismissive laugh, she was promptly
kicked out of the mansion. (Years later I found a taped copy of the interview in Hef’s press collection
with a skull drawn on the label. He must have really hated that one!)
I would be lying if I said I still didn’t have dreams of one day scoring a pictorial in Playboy’s
iconic pages, and mansion parties were a fun way to spend the weekend, but my main focus was
either pursuing an acting career or going back to school. I didn’t have time to be Hugh Hefner’s oncall
trophy girlfriend seven days a week, nor did I really think I had what it took. When I first started
coming around, Hef was dating the Bentley twins—those two sophisticated glamazons that seemed to
pay homage to the glory days of Playboy. With the right hair and makeup, I considered myself a pretty
girl, but Mandy and Sandy looked like movie stars. After they departed the mansion, the “Sloppy
Seven” invaded and lowered the bar.
It’s almost unsettling how quickly your priorities can shift.
Over the past year, I had been working long hours to afford my rent and I’d been auditioning like
crazy. Luckily, I had no trouble getting an agent—and even managed to land a few bit parts here and
there. They didn’t pay much, but it was enough to encourage me to continue pursuing my dream. My
two closest friends hadn’t been as fortunate. Heather had given up and decided she was moving back
to Pittsburgh. My roommate Nora hadn’t landed a single thing, either. The lease on our apartment was
ending and she told me that her parents had agreed to pay her rent on a new lease—but only if she had
her brother (an alcoholic who needed constant babysitting) move in. Just like that, I had to go.
It was like that scene in Bridesmaids where Kristen Wiig gets booted from her apartment by