Down the Rabbit Hole - Holly Madison

“boyfriend,” and like the socially awkward person I was, I asked her, “Do you feel like he even takes
you seriously when you live with Hef?”
My intention wasn’t to be mean; I actually wanted these girls to like me! I was genuinely curious.
When I shared the news that I’d be moving into the mansion, I hadn’t met the warmest response, so I
wondered how everyone else’s friends, families, and even boyfriends felt about it.
Tina whipped her head in my direction and snapped a dismissive response at me. I grimaced and
tried to apologize, but Tina wouldn’t even look at me. She just rolled her eyes at Vicky.
As you could have predicted, Tina’s boyfriend didn’t stick around long. In fact, none of the “side
boyfriends” ever stayed longer than a few months at most. I don’t think the men took them seriously. I
always assumed most men were just using the girls to check some Playboy Bunny fantasy off their
bucket list. I only ever saw one “side boyfriend” stick around: Hank Baskett.
Following the rules wasn’t difficult for me. I didn’t know too many people in Los Angeles and I
quickly cut out the small group of friends I did have—either because I didn’t want to be subjected to
their judgment or because they started to call asking for invites to the mansion and other favors I
couldn’t grant. Plus, I’ve always been a bit of a homebody and much preferred the delicious homecooked
meals the staff provided to dancing the night away at nightclubs (where I would usually get
pretty drunk purely out of sheer boredom). Most of the girls would have rather died than sit around
the dining table with men three times their age, but I found Hef’s friends funny and interesting, and
genuinely enjoyed listening to all of their stories. Eventually, I would convince myself that this was
yet another component of the common ground Hef and I shared as a couple.
Usually the movie nights included a steady rotation of Hef’s favorite classic films and I adore
old movies—something we were truly starting to bond over. Every Sunday night, Hef’s office would
arrange to have studios bring in movies that were still in theaters—and armed guards would enter the
mansion with giant film cans to screen the newest Hollywood blockbuster for us. It was pretty cool,
but it also was sort of bizarre, because oftentimes celebrities or other important Hollywood power
players would join us for the screenings and be relegated to spending roughly two hours squirming in
uncomfortable metal folding chairs. For being a super upscale home, it wasn’t without its downscale
touches. One of the most memorable was the tray of Johnson’s Baby Oil, Vaseline, and Kleenex that
was in every bathroom, in the grotto, and at the tennis courts and the pool bar. I still don’t know
whether to be disgusted or amused by those trays.
At first, my constant attendance at all of the events deemed “boring” by the other girls earned me
a bit of good grace with them. They felt that I took some of the attention off their recurring absences
while they busied about with their outside lives. Girls would find crafty ways to sneak out past
curfew when they thought it wouldn’t be noticed—like hiding in the trunk of someone’s car as they
drove off and onto the property!
While evenings at the mansion were pretty regimented, during the day we were virtually free to
do as we pleased. Hef was usually awake by 10 A.M. for breakfast, then meandered down the hall to
his office wing, where he would work on the magazine, various book projects, and other business. He
wouldn’t emerge again until the evening.
In the beginning, I spent most days with Britney—a nice girl that I had met at the Sunday pool