Down the Rabbit Hole - Holly Madison

that skinny could ever think she was fat, but I suppose I was a product of my environment. After
spending much of my adulthood as nothing more than a trophy girlfriend whose sole occupation was
to look good, I guess I can’t really blame myself.
On the night of Hef’s 78th birthday party we made our entrance into the great hall around nine
o’clock. Hef’s photographer Elayne snapped our obligatory photos. As was customary, Mark Frazier,
the body painter, brought the “Painted Ladies” over for a photo with us as well. Kendra was already
carrying a tray of Jell-O shots and she nervously offered them to us. Bridget, Hef, and I happily took
one each as the Mean Girls just ignored her with an icy coldness.
Hef wasted no time inviting the “Painted Ladies” up to his bedroom. Nicole was physically the
least Hef’s type, with her curvier body and strawberry-blond hair, so I knew right away that she
wasn’t making the cut, despite her participation in the sack.
Tiffany was the only one who wasn’t willing to go all the way (Good for her!), so even though I
really liked her, I knew she wasn’t going to be invited back.
Through the process of elimination, the 19-year-old platinum blonde from San Diego was in
position to be Hugh Hefner’s next girlfriend—if she played her cards right. In Kendra’s book Sliding
into Home, she describes Hef asking her to be a girlfriend and handing her a house key before he
invited her up to the bedroom. Now, I don’t know if Kendra is trying to sound extra-desirable,
innocent, or if her memory is just super rusty, but of course that’s not how it really went down. Hef
isn’t stupid. He never asked anyone to become a girlfriend before they joined him in bed. And he
never made a habit of carrying around extra sets of room keys.
Because Kendra seemed pleasant, Bridget and I started encouraging Hef to ask her to move in.
We openly (and loudly) chatted about how nice we thought she was.
“I don’t know . . . she doesn’t seem to have much personality,” Hef responded.
I rolled my eyes. Since when did he care about personality? Only a positive comment from
Bridget or me could turn Hef off to this girl who was so clearly his type. Did I mention he hated it
when his girlfriends got along? I could see what he meant, though. In the early days, Kendra wasn’t
the bubbly, bouncy loudmouth you may remember from The Girls Next Door. Her personality could
best be described as “deer in the headlights.” It was difficult to get a word out of her, and she seemed
to have fried her brain somewhere along the course of her life. At the time, I just assumed she was shy
or afraid of making a misstep while trying to navigate Hef’s world.
Despite his supposed reservations, he did continue to have her as a guest at the mansion. Kendra
was still living in San Diego at the time, so Hef invited her to stay through a whole weekend and join
us for the big Easter celebration that Sunday. Bridget and I had gone down to Melrose to pick out
matching dresses for the festivities—including one for Kendra. I knew she didn’t have a ton of clothes
and was probably stressing out just like I used to.
Usually I wouldn’t be so eager to dress like anybody’s twin, but I knew how adorable Hef
thought it was when the girls dressed alike. After nearly three years at the mansion, I was pretty
attuned to Hef’s preferences. I imagined him seeing the three of us together in matching outfits and
thinking, “Oh, how cute.” By getting Kendra to dress the part of a new girlfriend, I hoped it would
help Hef make up his mind and set us apart from the Mean Girls, who would most likely show up to