Down the Rabbit Hole - Holly Madison

“I’d love to come along with you the next time you all go out,” I said, bracing myself for a less than
exuberant response. Much to my surprise, he immediately took to the idea and invited me to join them
that coming Wednesday.
“Awesome,” I cheered, with a little hop. “Thank you!” Hef seemed amused by my childlike
excitement, but quickly turned back to his friends.
When I found Vicky to share the good news, she filled me in on all of the details: I was to meet
Hef and the girls at 10 P.M. in the mansion’s main entry hall dressed to impress in my sexiest club
wear before heading to Las Palmas—Hollywood’s hottest nightclub.
Every girl at some point has uttered the phrase, “I have nothing to wear.” But in my case, it was
sort of true. I spent the next three days staring at the approximately 10 items of clothing hanging in my
closet wishing that something appropriate would magically appear. I figured that if Hef approved of
how I looked, maybe he would consider offering me a role as a “girlfriend.” It felt like a long shot,
but there was always a chance. And my alternate options were becoming more and more grim. I
would not be going back to Oregon. I just couldn’t! Still, I was too embarrassed to ask any of my
friends to borrow anything—probably because doing so meant I would have to field questions I
wasn’t prepared to answer.
Eventually, I decided to pair a black miniskirt (which, despite its name, was about three inches
longer than anything any of the girlfriends wore) and a baby blue top with metal mesh overlay that
tied in the back. After analyzing my every angle in the bathroom mirror, I took a deep breath, jumped
in my car, and made the 10-minute drive to Hugh Hefner’s place. I pulled into the driveway at 9:55
P.M. petrified that I would be the last to arrive—I’ve always been a stickler for punctuality. I quickly
discovered that was a rarity at the mansion. I waited in the entrance hall for more than 10 minutes
before any of the ladies made their way down the cascading old English staircase. There was another
girl waiting downstairs named Candice who appeared to be “auditioning” for the open girlfriend spot
as well. She was quick to tell me that she had already been out with the group the previous Friday and
also how fond Hef was of her.
Oh shit, I thought, maybe I was a day late and a dollar short. Candice might get offered the
empty girlfriend spot before me.
In passing, the mansion looks decadent, but when taking the time to truly look at some of the
nooks and crannies, it’s amazing how neglected it was. I would come to refer to the décor as “ ’70s
porn chic.” At the time, there were nine dogs living in the mansion (most of them named after fashion
designers or luxury car brands, naturally), and the ancient yellow carpeting on the grand staircase was
covered in urine stains. I remember thinking that the carpet must have been older than any of his
girlfriends. That being said, at the time, it was by far the nicest home I’d ever stepped inside.
Finally, the girlfriends emerged in ascending order: newest to the oldest. At that particular time,
the cast of characters was a motley crew of bottle blondes: a quiet girl named Carolyn, upcoming
Playmates April, Adrianna, and Lisa; Vicky; and Tina Jordan (Hef’s “main girlfriend”). The scene
was almost comical as each girl bounced down the Gone With the Wind–esque staircase like a
carbon copy of the girl before her: white-ish blond hair in large barrel curls, the skimpiest sparkly
dress imaginable, and the kind of strappy platform heels you’d expect to see on stage at a strip club. I