Down the Rabbit Hole (6 page)

Vicky had once given me a peek inside her room—and I was surprised at how much it looked like the type of room I would have liked to have. The plush bed was covered in pink candy-striped satin sheets and piled high with Playboy-branded clothing—free gifts for Hef's girlfriends. Disney paraphernalia was everywhere from a recent shopping spree at Disneyland—all on Hef's tab, of course. And a dreamy windowseat overlooked the backyard.

We even ordered cheeseburgers from the kitchen, which may not sound like much, but it was. Once upon a time, Hef's guests could order whatever they wanted from the kitchen, whenever they wanted. It was even said that Jack Nicholson used to treat the mansion as a drive-thru back in the '70s. He would call the butler's pantry ahead of time, order a meal, and have it brought out to his car as he drove up the driveway. After the food was delivered to him in a paper sack, he would supposedly speed out the back gate without so much as a hello. Since then, guests' access to the kitchen became a little more limited, but Hef's girlfriends could still order whatever they wanted, 24 hours a day. To me, someone used to scraping together pennies in order to eat at Burger King, this was on another level!

I had to admit: the whole girlfriend thing was starting to look pretty appealing.

Around that time, a few of the girls had suggested that I come out with them for one of the biweekly club nights. One of the girlfriends, Kimberly, had recently been kicked out, which meant there was an open spot Hef was ready to fill. “Talk to Hef,” Vicky encouraged after I confided in her about my housing problems. Never did it occur to me to simply approach him myself. It also never occurred to me that the then-seven girlfriends wanted me around only because my “ordinary” appearance was nonthreatening. They wanted to make sure whoever filled the empty space wasn't competition.

On Sunday, I worked up the nerve to mention the idea to Hef when he finally appeared poolside. “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 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 attention of the resident doormen stationed behind the red velvet rope. From the looks of it, you would have thought Oprah was inside giving away free cars. As the limo door opened, four security guards rushed to part the sea of club-goers so we could make our way inside. I had been to nightclubs before, but I was usually one of those unlucky souls not “on the list” and relegated to the milelong line that wrapped around the block. I was one of the first to step out of the limo and every set of eyes turned to check if I was someone worth knowing. I started fussing with my top, unnerved by this unexpected attention. One by one, each bottle blonde piled out of the limousine—waiting for Hef before we made our way inside. Vicky must have noticed the astonishment in my eyes because she leaned over and whispered, “ 'NSYNC
and
Christina Aguilera were here the last time we came.”

When Hef finally emerged from the car, the crowd went wild. People were shouting his name and shoving one another to get a better look. He lifted a hand to wave to the crowd as if he were some kind of dignitary. The whole thing seemed incredibly strange to me, but for Hef it had become a regular part of his weekly routine on the L.A. club scene. For decades, Hef was an infamous homebody. After all, he created his own version of paradise at the Playboy Mansion, so why would he ever want to leave? Throughout the '70s, '80s, and '90s, it was extremely rare to see him out and about. In 1999, when he separated from his wife of almost 10 years, Kimberley Conrad, a few of his friends persuaded him to leave his compound for a night on the town. What happened next was a surprise to everyone. People went absolutely crazy to see this 70-something icon from another era at an L.A. nightclub. Shortly thereafter Hef instituted his biweekly club nights.
Rolling Stone
magazine called it “Hugh Hefner's Resurrection.” (I would later learn that this sort of behavior wasn't atypical. The only thing Hef loved more than the mansion was himself. The sort of super fandom he saw at these nightclubs was all the fuel this senior citizen needed to keep painting the town red.)

It was during one such evening, after his separation, that Hef met Sandy and Mandy Bentley. Immediately he began dating these two blond bombshells, along with another blonde, Brande Roderick. This unusual foursome made Hef even more of a sensation. The age difference, the number of girlfriends, the hint of incest, the fact that all three of the girls' names rhymed, along with Hef's constant public insistence that he had to take Viagra to keep up with all of these women made the situation truly bizarre. In Los Angeles the bizarre is often appreciated, if only momentarily, and at that moment in time Hef and his blond entourage had become adored mascots of the L.A. nightclub world.

As soon as we entered past the velvet ropes we were whisked away to a private area next to the dance floor. Hef settled into the plush booth flanked by Tina and Lisa. Our VIP table was already stocked with an array of alcohol and mixers—this was the golden age of bottle service and Hef indulged in every luxury. Security lined the velvet ropes separating our table from the rest of the crowd. If a guy was brazen enough to try to get the attention of one of the girlfriends, security would block them from our table—and occasionally escort them outside, depending on how persistent he was. Since most nights the girls were locked up in the mansion like some twisted version of Rapunzel, they used these evenings out as opportunities to meet other men.

Yes, most of Hugh Hefner's girlfriends had other boyfriends. In fact, during my time at the mansion, I can only say for sure that two of us remained faithful (my future BFF Bridget Marquardt and myself). Needless to say, this was all very hush-hush, because Hef strictly forbade any of his girlfriends from dating other people. While Hef could date an entire sorority house full of girls, we were to remain totally loyal. Looking back, I'm pretty sure that rule existed not so much because Hef was jealous of other men, but because the truth would have burst the public persona he had spent decades crafting. Girls who were caught “cheating” on Hef would be thrown out of the house immediately. While the girls took that rule extremely seriously, it didn't mean they would actually obey it. So, on these club nights, the girls would dip off “to the ladies' room” and head to a corner of the bar hidden from Hef's view, making “friends” and exchanging numbers with men . . . like normal 20-something girls
should
be doing.

I stayed close to Vicky most of that night and followed her lead: dancing, drinking, and making sure to pay lots of attention to Hef. At one point when he stood up to dance with us, his rhythm was so off that I was certain he was joking and let out a big laugh. Vicky shot me a look that made it very clear: he was
not
joking. Luckily, he didn't register my laugh as mocking and continued dancing.

Oh my god,
I thought, genuinely mortified for him
.
Had no one told him how silly he looked? He pulled out some truly ancient dance moves that I can't imagine were remotely cool in any era other than the '70s. I felt a bit sorry for him dancing around like the punch line to a bad joke.
Did they always allow him to look so foolish?
I wondered why these women, his seven dingbats, didn't care enough to protect him from the embarrassment—surely they owed him at least that. And worse yet, they encouraged his awkward dancing about. Back then, he seemed like such a sweet man to me and this felt unnecessarily cruel. Regardless, I knew it wasn't my place to break the news to him—not that night anyway. I was so eager to make a good impression that I could hear my heart in my ears. I was grateful that Hef allowed me to tag along in the first place. He seemed like a good man and talked as if he wanted the world for his girls.

But like all that glitters and sparkles, this opportunity wouldn't come without a steep price.

“Would you like a Quaalude?” Hef asked, leaning towards me with a bunch of large horse pills in his hands, held together by a crumpled tissue.

“No thanks,” I answered cheerfully, as if I were interviewing for a job. “I don't do drugs.”

“Okay, that's good,” he said nonchalantly. “Usually I don't approve of drugs, but you know, in the '70s they used to call these pills ‘thigh openers.' ”

I laughed nervously—unsure of what to say. I was proud of myself for saying no; it was the right decision. I still felt in control of the situation and was prepared to tackle whatever came my way with sober eyes.

Today, I want to scream “PAUSE!” and freeze frame that moment of my life back in late August 2001. I want to grab that young girl, shake her back into reality, and scream, “What the hell are you thinking?”

Hef was a notoriously lecherous 70-something old man offering me Quaaludes that he referred to as “thigh openers.” Are you kidding me? Why didn't I run for the nearest exit? It doesn't get much creepier than that.

But I suppose I had already made up my mind at that point. Looking back, I can't imagine what I
was
thinking, but I'm also so far removed from what I was feeling back then. I was about to be homeless. I had no place to go and was panicking over what to do next when this opportunity with Hef just sort of fell into my lap. If I became a girlfriend, I would have somewhere to live. If I became part of
Playboy
's inner circle, perhaps that could even help my career. It felt as if my stars were starting to align. I decided to take the chance and see what this strange, legendary world was all about. For as long as I could remember, I had been searching for a great adventure, and this was already the craziest night I'd ever experienced. Like watching a bizarre old movie, I was utterly transfixed by this strange universe.