Down the Rabbit Hole - Holly Madison

so long, this box was my nemesis, as I dreaded possible new additions to the harem. This time,
however, I was determined to finally use the box to my advantage.
Bridget and I were beyond tired of the Mean Girls, but we knew Hef wouldn’t be content with
just the two of us. We just got along too well for his taste. How could Mr. Drama King feel fought
over, coveted, or interesting if his girlfriends actually got along? I knew Hef felt he needed to be seen
with a gaggle of women in order to keep up his macho Playboy image, and since he viewed Bridget
and me as virtually the same person, I knew a new girlfriend would have to move in in order for us to
have a chance at getting rid of the others.
The Mean Girls had already checked out, mentally. Daphne, Dianna, and Elizabeth had been at
the mansion for more than two years—and by this point probably assumed they’d never be offered a
pictorial. They each began focusing more on their lives outside the gates (aka other boyfriends, in
some cases), so it was only a matter of time before they moved out or Hef asked them to leave. But
even that wasn’t soon enough. Bridget and I knew that if we wanted any sort of influence in kicking
these girls to the curb and figuring out who their replacements would be, we’d have to act quickly.
A few days before Hef’s 78th birthday party, I noticed three pictures stacked in front of the
wooden box in Hef’s closet. I grabbed the photos and info sheets to scope out our options: Tiffany,
Nicole, and Kendra. Apparently, the girls were auditioning to be “Painted Ladies” at the party, and
the body paint artist had submitted the images to the mansion for approval. The photos eventually
made their way to Hef’s private “consideration” pile, which meant he would definitely be keeping his
eye out for them at the party.
The day of Hef’s soiree, Bridget and I went downstairs to the gym to meet the “Painted Ladies”
as they got ready (it took most of the day for these girls to get covered head to toe in body paint). All
three girls seemed nice enough, but Bridget and I decided that Tiffany was our favorite. She was easy
to talk to and seemed really smart—plus, she had a knockout smile, long ash blond curls, and a
gorgeous naturally curvy body. More than hot enough to be Hef’s girlfriend, but a refreshing change
from the bleached-blond Fembot look.
Unbeknownst to us at the time, Hef had also made a pilgrimage down to the gym to check out the
prospects and made a beeline toward Kendra Wilkinson—the most platinum and plastic of the bunch.
Preparing for a mansion party took an entire day. The large parties were the highlights of
mansion life, so the girlfriends were expected to look flawless. Couple that expectation with the fact
that we girls had a lot of time on our hands, and you get marathon “beauty days.” All of the girls
started their day visiting the salon to spend hours on an elaborate hairdo. That year I had purple
streaks clipped into my long blond extensions. Costumes were customized down to the tiniest detail
and diets were strictly observed in the weeks before a big party. I was so critical of my appearance
—particularly my weight. A girl could rarely be too skinny at the mansion. After all, there were
expectations that we become the Playboy fantasy everyone expected us to be. And in order to be that
woman, it was essential that we looked the part.
Plagued by self-doubt, I was constantly troubled by an imaginary belly and would often add a
single garter to my costumes to hide a tiny dot on the back of my left leg. God forbid, someone might
think I had cellulite. These days I look back at photos from my mansion days and marvel how a girl