How Ex-Playboy Girlfriend Holly Madison’s Memoir Sucked me “Down the Rabbit Hole”

It may come to a surprise to some of my fellow moms, but I was a HUGE fan of “Girls Next Door,” the reality TV show centered on the day-to-day lives of Playboy founder Hugh Hefner (aka “Hef”) and his three live-in girlfriends — Holly Madison, Bridget Marquardt, and Kendra Wilkinson. DownTheRabbitHole Cover

While I didn’t watch the show, which aired 2005-2009, regularly, when I did, I found it to be a fun, fluffy, wonderful guilty pleasure — an inside peek at a life I might’ve lived had I been just a shade blonder, gotten a boob job, and high tailed it to Los Angeles in my late teens.

As I watched each episode, I found myself increasingly drawn to Girlfriend #1 Holly Madison — formerly Holly Sue Cullen — who grew up in Oregon and Alaska. While the most serious-toned of the three blonde girlfriends, she was also the only one who seemed to aspire to having a family as well as a career. Beautiful and humble, Holly stood out from over-the-top bubbly Bridget and air-headed Kendra as someone I would enjoy spending time with over a cup of coffee.

So when I finally laid my hands on Holly Madison’s “Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny” on June 23, I simply could not put it down. I finished it in one week. This is a huge accomplishment considering I am raising two toddler sons. (I can barely find time to clean my kitchen most days, let alone read a memoir!)

There are two reasons the book sucked me in from the first page: one, it offered extraordinary insight into the inner workings of one of the most fascinating and salacious lifestyles. I found myself riveted by the descriptions of the rooms (“downscale” touches like Johnson’s baby oil in the poolside washrooms; puppy urine stains on the mansion’s staircases); the ladies who inhabited them (like the girlfriend who solicited other girlfriends for a high-end prostitution ring); and the conversations (such as Hef’s condescending way of explaining old movie plot lines or throwing a fit over Holly wearing red lipstick).

The other reason was that it struck a raw nerve in me. I’m no Playmate or pageant queen (though I was “Miss Nina” at the Baltimore Columbus Day Parade in 1992 and once runway-modeled Uzbekistani clothing for a festival in Washington, D.C.). Still, I know what it’s like to be valued for your looks, or to feel like your best asset is your beauty, a temporary gift.

Being a girlfriend to an old dude like Hef isn’t glamorous, and Holly’s memoir confirms that. Her descriptions of the post-nightclub sex orgies, in particular, are wince-worthy. And while Holly does acknowledge the perks of the Playboy girlfriend lifestyle — like a $1,000-a-week clothing budget — she spares Hef little mercy when she spotlights the ulterior motives behind his seemingly kind, friendly demeanor.

Among other things, the Playboy founder, who is now 89 to Holly’s 35, had a primary interest in keeping up an image that other men would envy. He couldn’t go without a girlfriend for even one day. In reality, says Holly, he threw immature temper tantrums and would play the girlfriends against each other (for example, by complimenting Kendra’s red lipstick just a few years after lambasting Holly for wearing it). The details are so rich and believable that I think it would be difficult for anyone to discredit her (though Kendra, perhaps out of jealousy, is trying).

One might wonder, then, how smart women like Holly or bestie Bridget (who apparently has a master’s degree) would put up with the Hef monster for years on end. Was the prospect of fame really that alluring? If we believe Holly, the answer is yes: Hef always dangled the possibility of better things — a monogamous relationship, a Playboy centerfold spread — just close enough to keep the girls loyal:

“I had to believe that there was a greater purpose for the choices I had made: whether it was to help advance my career or whether it was truly for love,” writes Madison. “And depending on the month, the week, and sometimes even the hour of the day, I would waffle back and forth between precisely why I was living a life as nothing more than ‘Girlfriend Number One’ to a man who was old enough to be my grandfather. I didn’t want to admit that I had sold a bit of my soul for the chance at fame.”

If Holly’s intent was to make me angrier at the double standards imposed on women, then she was successful. By the end of the 405-page read, I found myself almost teary-eyed, cheering on the new mom as a modern-day example of courage, strength, and beauty.

The only thing I’m still bothered by is that the tone of “Down the Rabbit Hole” is about 85% anger and 15% gratitude. Let’s not forget that being Hef’s main squeeze afforded Holly all kinds of opportunities, from celebrity status to the funds to pay off her $7,000 breast implants. Were it not for Hef and the lucky chance that reality TV would take off and make her a household name via “Girls Next Door,” Holly would have probably have left L.A. a long time ago, like most of her friends.

Unfortunately, for far too many women, fame and opportunity comes at great personal cost, whether it’s the woman who stalls childbearing to further her career (only to discover fertility challenges later on), or the woman who must pretend to be turned on by an 80-year-old man in order to have any chance at making more than a waitress’ wage.

And while Holly got her happy-ever-after ending, most women need more than a great pair of fake tits and blonde hair to elevate their careers.

I would love to see the day where a female magazine mogul were wealthy and powerful enough to afford and attract seven 20-something boyfriends. But would anyone watch a show about it? While many men are inspired by the idea of having a harem of young things to cater to their every whim, most women I know need their lady heroes to overcome major challenges and rise above, just like Holly did when she said “screw you” to mansion life.

2 thoughts on “How Ex-Playboy Girlfriend Holly Madison’s Memoir Sucked me “Down the Rabbit Hole”

  1. Hi, you have some incredible articles on LearnVest! As a freelance writer, I wanted to see if you wouldn’t mind shooting me an email to talk about your freelance writing career and how you became a contributing writer. If you’re up for the convo- would you mind hitting me up at Jennifer.l.hargraves@gmail.com? Thanks!

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