Down the Rabbit Hole - Holly Madison

Mean Girls came in to present him with the gift. As he fawned and cooed over the picture, I noticed
the girls exchange a few sly glances and smirks. It was as if they were saying: “See how great we all
look . . . without Holly and Bridget.”
If Bridget or I had chosen to get a gift for Hef without including the other girlfriends, we would
have been reprimanded for not including everyone. Yet no one—Hef included—acknowledged my
presence in the room or my glaring omission from the drawing. It was as if I were a ghost.
What Daphne and Dianna didn’t realize is that they’d never be able to push Bridget and me out
as long as they were still aligned with Elizabeth and Whitney. Shrill Elizabeth and “pushy” Whitney
were never Hef’s cup of tea. I heard he turned each of them down the first time they had asked to
move in, but eventually he kept them around as filler—so he could reach the “seven girlfriends” quota
that had become his trademark. (Over the previous year or so, since his girlfriends hadn’t been
gracing the pages of the magazine as often as they once did, the number of girls clamoring to be
included in his “party posse” had understandably subsided.)
Whitney had always been Hef’s least favorite—in part because she came into the group under
some unsavory circumstances.
“Hef, do you think Whitney could start getting an allowance?” Tina had asked. Despite having
left the mansion months earlier, Tina still trotted around from time to time to see what she could
squeeze out of Hef. “She works really hard to get all dressed up for you and to come to all the events.
She’d make a really great girlfriend.”
At the time, Whitney was good enough to join him in the bedroom, but he wasn’t too keen on
asking her to move in. Tina had clearly been recruited to go to bat for her.
“Actually, Tina, I’m hoping that with this next set of girls, expectations won’t be so high,” Hef
explained to his former girlfriend. “Do you know I spent two million dollars just on girlfriends and
trips in the past few years?” (Most of that went towards the private planes he chartered, sometimes on
the company tab, and the trips he took his girlfriends on—including a lavish European tour before I
had arrived.)
“She’s putting in all this time and all she’s getting out of it is a drink and a fuck!” Tina said,
clearly frustrated that she wasn’t getting her way. Like I said, this girl was a hustler.
God, I thought. I could never get away with talking to Hef like that.
The room got very silent as Hef sat staring at Tina.
“I like to think of this as all of their dreams coming true,” he said very solemnly. Even Tina was
struck silent by how serious he was. Did he really mean what he was saying? It sounded so conceited
to assume that simply being in his presence (or bedroom) was a “dream come true” for these women.
The “hurt” expression he held on his face forced Tina to abort her mission.
“Okay, sorry,” Tina offered and leaned over to give him a peck on the mouth. As she walked out
the door, she called out a thoughtless “Love you!”
For months Hef continued to reject Whitney’s pleas to become a girlfriend, but eventually her
persistence paid off and one day she moved into the mansion. We quickly discovered she was a
pathological liar—and it was actually pretty amusing. Her age, former professions, and life story
changed daily.