Down the Rabbit Hole - Holly Madison

thought it would be a great way to share the celebration with all of her friends that couldn’t be there.
Bridget, Kendra, and I couldn’t have had a better time. For whatever reason, Hef wasn’t
interested in attending, but I can’t imagine his cranky, high-maintenance personality in laid-back
Jamaica anyway. The three of us girls had an amazing few days at Sandals Negril, relaxing, ziplining,
and exploring with my family. There was no drama, just a truly memorable trip and a beautiful
beach wedding. I was the maid of honor, my sister looked stunning, and my family and two closest
girlfriends were as happy as could be. Who could ask for anything more?
Playboy could. Just before filming was set to begin on season five, there was a mad rush to get
Bridget, Kendra, and me under contract. Prior to the first episode of the series, we had each signed
the most basic of television releases—and nothing more.
Realizing that the stars of this hit show were theoretically free to walk away and pursue other
television opportunities at any time, someone must have panicked. Unbeknownst to us, Hef arranged
to have us contracted under Alta Loma (Playboy’s production company), which basically meant that
we would have a talent agreement binding us to Hugh Hefner. Letting us negotiate directly with the
network was never going to be an option, probably because it meant he would have had to relinquish
too much control over his girlfriends. After all, what if E! offered us something greater than being one
of Hugh Hefner’s blond bimbos? As I understood it, the network was willing to work with us in this
fashion as long as Alta Loma could show they had us under contract, and fast.
It all happened so quickly, I can’t even remember how I initially heard about the contract. What I
do recall is getting really worked up and marching down to the master bedroom to tell Hef I had no
intention of signing.
“I think it’s in bad taste to sign a contract to be your girlfriend,” I maintained. Given that the
show was about “Hef and who he is dating,” as opposed to any of the three of us (as they liked to
remind us regularly), I felt signing a contract with him was taking away my option of walking away
from the relationship at any time. It would be just another facet of this relationship that would make
me feel like a hooker. “It’s just weird.”
“I understand the notion, but it’s important to me that you sign it,” he said, looking at me with sad
puppy dog eyes. “If you care about me, you’ll do it.”
In the end, it was always about Hef. Quietly, I did my best to consider my options. I didn’t want
to be coerced into doing anything else for this man.
Sensing my hesitation, and realizing that my heartstrings might not convince me, Hef decided to
appeal to my business sense, telling me that if we didn’t all sign, the network might not order another
season.
As further encouragement, Hef had told me Bridget already signed her contract, but I didn’t learn
until afterwards that she did so completely against her better judgment. As a reasonable person
would, Bridget asked to have some time to have her lawyers look over the paperwork but was
denied. I imagine she was given the trademark mansion attitude: “If you don’t like it, you can leave.”
Begrudgingly, she signed the contract.
“Okay,” I finally relented. “I’ll look at it, but I want you to know, I don’t like this.”
“I understand,” Hef said, unable to contain his smile. He didn’t care what the hell I thought, as