Down the Rabbit Hole by Holly Madison Read Free Book Online

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 would have thought Hugh Hefner preferred his girlfriends sexy and retro, but his taste was surprisingly . . . well, cheap. As for Tina and Hef, they would never arrive until everyone was already in place—like some antiquated nod to the hierarchy that existed.
    One of the butlers arranged us in the hall and snapped a few pictures for Hef’s scrapbook before we piled into the limousine—another Playboy tradition to satisfy Hef’s endless desire for mementos (the next morning prints would be placed outside each girl’s bedroom door, which only amplified the massive pressure to always look perfect and caused the girlfriends to spend hours critiquing their appearances).
    When we finally arrived in Hollywood, the scene outside of the nightclub was absolute chaos. Hundreds of men in Von Dutch trucker hats and women in their obligatory low-rise Frankie B. jeans and fedoras (because in 2001 every club girl was just dying to be mistaken for Britney Spears) were bombarding the entryway, clamoring over one another to get the