Down the Rabbit Hole - Holly Madison

AS SEASON TWO OF Holly’s World wrapped, Lifetime TV was preparing a special on Hef and
Crystal’s upcoming June wedding, but it wasn’t to go on as planned. Crystal ended up running out on
Hef five days before the 300-guest ceremony was set to take place. The crew was left with nothing to
film. I couldn’t begin to imagine how mortified Hef must have felt. Hef’s friends and many Playmates
were in an uproar, denouncing Crystal, sometimes publicly on social media. Kendra and I were asked
to film a scene with Hef to help fill time in the special, which was now titled Hef’s Runaway Bride. I
did it as a favor to production, the same people behind Girls Next Door and Holly’s World , not Hef,
though I do have to admit, despite all the negative things I had been through with the guy, I did feel
bad for him after such a public humiliation. I wasn’t interested in showing up to say “I told you so”
regarding Crystal, I just wanted to try and be a friend.
I flew into L.A. the day of the shoot and arrived at the mansion early to wait for the production
crew in the unusually silent great hall. Suddenly, a bleary-eyed blonde wearing a pair of Hef’s
oversize aqua silk pajamas and a noticeable case of bed head appeared at the top of the staircase.
“Excuse me,” asked Shera Bechard, a recent Playmate who had obviously just wandered out of
Hef’s bedroom, “how do I take the dog out?” She pointed down at a King Charles spaniel, the dog
Crystal had left behind, who was sitting at her feet.
“Um, you just open up the door and take him outside,” I said, trying my best not to sound
condescending. It was a strange question with an obvious answer, but then again, the mansion was
such a bizarre place it would have been easy to assume that there was probably a weird ritual
involved with taking one of the mansion’s dogs outside. Thankfully the crew showed up and ushered
me down to Mary’s office, saving me from that awkward exchange with Hef’s latest concubine.
As Kendra and I sat in her mansion office, Mary explained that she had received a call from
Crystal when Crystal was at the Jazz Festival. Crystal confided in her that she was really nervous.
Mary said she had asked her if the problem was Anna (Anna was one of the two girls Hef was
supposedly dating when he was “settling down” with Crystal), and Crystal had said no, that she loved
Anna. Mary just shrugged and said she didn’t know what happened between Crystal and Hef.
By then, we had all heard the gossip that Hef and Crystal couldn’t come to terms on a prenup,
leaving them at a stalemate just days before the wedding. So Crystal decided to up and leave—
straight into the arms of her secret boyfriend, Jordan McGraw (the son of Dr. Phil . . . what would he
have to say about this little love triangle?). One celebrity news site even revealed that she had moved
in with him.
It was the giant elephant in the room, but neither Kendra nor I breathed a word of it. After all,
we had a film crew surrounding us and we all implicitly knew that that topic was not something Hef
would allow to be included in the special.
Kendra and I sat down with Hef in the mansion library, a room I had been in a zillion times
before, but I had never been this uncomfortable. Despite the years that had passed, there we were—
Bridget, Kendra, and me—hanging on the wall. It was a photo from our first pictorial, the three of us
piled naked on top of one another. Living at the mansion you start to get desensitized to those sorts of
things. Nude photos, no matter how explicit, had all started to look the same to me. But after being
away from Playboy for three years, the photo that had once seemed so silly and playful struck me for