Down The Rabbit Hole

“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. And depending upon 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.”

Holly reflects on a period when, early during her stay in a mansion, she was suicidal. As the girlfriend who slept with Hefner in his bedroom each night, whom he boasted was his one true love, Holly realizes that she has reached the height of what life with Hefner has to offer her. She asks herself what legitimate reason she might have for remaining in this setting. Although it offers her luxury, extravagance, and a modicum of fame, it restricts her possibilities and outside activities.

“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 decor 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.”

On her first night out as an official part of Hefner’s entourage, Holly notices the sham of the mansion’s presentation, as well as the silly hierarchy that dictates the order and sequential actions of Hefner’s seven girlfriends as they ride in the limousine to a nightclub with Hefner. Over the course of her seven years with Hefner, Holly awakens to the fact that the Playboy lifestyle is as much of a facade as the mansion itself.

“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 would 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.”

Her first invitation to join in the activities of Hefner’s girlfriends comes at a particularly vulnerable point in Holly’s life. At the time, she sees it as a golden opportunity. But, as was the case for so many other young women absorbed into Hefner’s orbit, the reality was that Hefner was exploiting Holly’s material vulnerability. As the narrative progresses, Holly discovers that Hefner had singled her out as a very attractive potential girlfriend on her first visit to the mansion. She was not as lucky to have wormed her way into the Playboy fold as she initially believed. In fact, Hefner was treating her in exactly the same way that he had countless attractive women before her: taking advantage of her need for economic support in ways that disproportionately benefited him.

“The next day, with a heavy heart, I called the general manager and let her know that not only could I not attend the pageant, I was quitting my job as well. […] In hindsight, that incident should have been a blaring indicator of what my life was going to be like behind those gates, but I still had high hopes.

I felt like my last shred of independence was gone. But at that point, I thought I’d seen the worst of it. It wasn’t an ideal world, but I could make it work. I could find some happiness here while I figured out my next move, I reasoned with myself. After all, it would only be a few months, maybe a year [...] at most.”

Only a few months into her stay at the mansion, Holly excitedly asks Hefner if she could leave for a couple of days to participate in a beauty pageant. It is sponsored by Hooters, the restaurant chain where she still works. Not only does he insist that she forgo the pageant, but he also forces her to quit her job altogether. This puts her in the position of choosing her freedom or remaining within his orbit. Hefner thus demonstrates his willingness to use Systematic Disempowerment to control Holly and his other girlfriends. Holly thinks that Hefner is perpetually close to asking her to leave the mansion. Ironically, his toxic manipulation—pretending to ignore her while limiting her outside activities—is evidence of his obsession with drawing her closer to them.

“Inside the mansion, life wasn’t at all like what I dreamed it would be. Instead of a nightly slumber party with six of your best friends, I had entered the lion’s den. It gave a whole new meaning to the phrase ‘keep your enemies close’ and made a sorority house look like a Bible study.”

One of the author’s most consistently expressed motifs concerns the heated rivalries between Hefner’s girlfriends. These often result in bruised feelings, estrangement, and treachery. As Holly progresses up Hefner’s hierarchy of girlfriends, she learns that Hefner promoting rivalry as a way of keeping the girls focused on his affection for them, rather than on their friendship with one another. In particular, he plays the other women against Holly by telling them that they should be good, as Holly is good.

“People often ask me if the girls were required to have plastic surgery while living in the mansion, because it was clear so many of us did. The answer is both simple and complex. No, we were not obligated to have plastic surgery while living there. However, the mansion was a virtual breeding ground for superficial insecurities. And most girls who live there ended up with body dysmorphic disorders. No matter how beautiful they were, these women would pick themselves apart—ordering one procedure after the next.”

Holly’s first few years at the mansion take a heavy toll on her confidence and self-image. In addition to having rhinoplasty, she develops a stammer, wrestles with suicidal ideation, and second guesses every decision she makes. Virtually all the other young women associated with Playboy experience similar levels of self-doubt. Hefner’s practice of intentionally stoking rivalry between them further amplifies their physical insecurities.

“The women were tempted with the lavish life that [Hefner’s] $1,000 weekly allowance certainly wouldn’t provide for. They would travel all over the world and make upwards of $25,000 to spend an evening with whoever was willing to shell out the cash. Girls were making money hand over fist! They became addicted to L.A.’s opulent lifestyle—expensive cars, designer handbags, luxury apartments—and sadly, for many of these women, the majority of their income went to supporting some pretty nasty drug habits.”

While discussing why so many Playboy girlfriends and Playmates moved to sex work, Holly is approached by another girlfriend who proposes that they work for a madam. For some women in the Playboy orbit, the allure of fabulous sums of money and world travel was too great to pass up. Their relative youth, combined with the chance to escape the cloister of the mansion, add to the attraction of sex work. Although Hefner tries to prevent Playboy women from becoming sex workers for other men, he unapologetically and hypocritically continues his personal sexual exploitation of them.

“Above all things, Hef is fascinated with fame (both his and other people’s). He is obsessed with cataloging his life as a public figure and keeps records of every press interview he’s ever done. Celebrity is one of the few things that can’t be bought—and Hef prides himself greatly on his 60 plus years in the spotlight.”

The author demonstrates repeatedly that the driving force behind Hefner’s Playboy Enterprises is the gratification of his ego. She details how he has kept 2,000 scrapbooks—for which he is included in the Guinness Book of World Records—and explains that his main concern is how others would perceive activities conducted in the mansion and in public by those affiliated with Playboy. He does everything possible to maintain his image as a unique, iconic person of great cultural importance.

“Usually Hef made a public fuss over whoever his main girlfriend was—I felt like I was the first one he neglected to do that with. It made me feel like I was not beautiful or glamorous enough to merit such praise. In hindsight, I know he was just sick of the high turnover with his past girlfriends. They were lasting, on average, about six months, and he was done floating any girl’s ego. He had come to the conclusion that if he kept us broken and needy, we would stay.”

The longer Holly remains in the Playboy Mansion, the clearer she recognizes the intricate way that Hefner manipulates the young women whom he calls girlfriends. In response, Holly works diligently to please Hefner, never disputing his will or asking for preference. In doing so, she unintentionally distinguishes herself from most of the other women involved with life at the mansion. Ironically, while the author perceives herself to be least favored of all Hefner’s “main girlfriends,” she is the one that he works most desperately to hang onto once she decides to leave.

“Playboy Enterprises (a public company at the time) owned the mansion. Not Hef. In order to live there, he had to pay a monthly rent on every room he and his girlfriends occupied. People may find it surprising that Hugh Hefner is nothing more than a tenant renting his room at the mansion but that’s exactly how it is. […] Since I lived in the “Vanity” corner of Hef’s closet he didn’t have to pay any rent on my account.”

During her years at the Playboy Mansion, Holly discovers many realities that bely the public’s positive perception of Hefner and his business. While Hefner pays tens of thousands of dollars each month to sustain his lifestyle, and the lifestyle of those in his orbit, Playboy Enterprises itself is suffering a lengthy downward economic spiral. It is also becoming a progressively less influential cultural force. Part of the reason that Hefner is loath to let Holly escape his orbit is the fact that her reality television program has brought new revenue and exposure to Playboy. Hefner works continually to perpetuate deceptive images of himself and his enterprises as unendingly successful.

“I was asked a question that threw me for a loop: ‘When did you first realize you were beautiful?’ I started a bit, taken out of my hypnosis by an out of the ordinary question.

‘I never did discover I was beautiful,’ I snapped. ‘I made myself beautiful.’

[…] One of the head producers would later say to me that this answer led him to believe that they had something with the girls and maybe there was more of a story here […] It was finally Lisa Berger then president of programming at E!, who suggested she would like to see what life at the mansion was like through the eyes of the girls: a Dorothy in Oz kind of take on the Playboy world.”

While interviewing for a potential role in a televised tour of the Playboy Mansion, Holly breaks from her robot-like responses with this surprisingly candid comment. Her authenticity helps the TV executives realize that Hefner’s three girlfriends have distinct personalities and ambitions. In doing so, it plants the seed for the highly successful Girls Next Door reality series. Recognizing the benefits of the series, Hefner allows it go forward while trying to keep a tight rein on the scripts and girlfriends’ actions.

“Feeling like I was at a breaking point, I told Hef that I needed to see a psychiatrist during one of my sob sessions, but my confession fell on deaf ears. He refused to let me see a therapist because, as he put it, a therapist would just tell me to leave the mansion.”

Readers may find this unguarded comment from Hefner to be a remarkably honest admission that, on some level, he knew how challenging it was to live within his orbit. Holly writes that she was chronically depressed and sometimes suicidal throughout her time in the mansion. However, she initially failed to understand that her surroundings were the source of her suffering. Regardless, Hefner eventually relents and allows Holly to see a doctor and take antidepressants. The plethora of drugs reportedly taken by other women in the mansion may have been attempts to self-medicate for similar issues.

“‘I can’t promise it, but you’re going to shoot a cover and I’m going to put you in the magazine,’ Hef said. It was in many ways the defining moment of my life. After four years of living there, I was finally going to fulfill my long-held dream of being in Playboy magazine. […] This man—who had conditioned us to believe we were good enough for his bed but not for his magazine—just made our dreams come true. It was well within his power all along, but he was finally saying we were worthy. It was validating and exciting all at the same time.”

Hefner discourages his girlfriends from appearing in Playboy pictorials because he knows that many Playmates achieve success and independence as a result of the notoriety they receive. From the beginning of their association with Hefner, the three remaining girlfriends all desire to appear in pictorials. Because they have become celebrities via their television program, Hefner can no longer prevent them from appearing in the magazine. As he expects, though, their three covers greatly enhance the popularity they enjoy independent of him.

“I presented Hef with the sort of sap-filled greeting card he adored […] As he read it aloud, I burst into tears. Hef put his arm around me and gave me a kiss on the head. He was positively glowing! […]

I tried to play off my outburst as having been touched by the romantic moment (and I think most people bought it!), but in reality I was crying because of what a farce this whole thing was and how stretched thin my nerves were at the moment. I had sold my soul to the devil and felt that there was no way out.”

This bizarre scene, in which Holly presents Hefner with an anniversary card, occurs on her fifth anniversary as his main girlfriend. Also present at this event are camera operators filming everything for their reality television show, along with the two other girlfriends with whom Hefner regularly sleeps. This contributes to Holly’s feelings of depression and absurdity. These feelings are ironic, given the newfound financial success and notoriety she has as a result of The Girls Next Door.

“I was finally starting to feel like I had a purpose, like I had some use in the Playboy world. I wasn’t just one of Hef’s numerous blonde bimbos. My confidence grew for the first time since I had moved into the mansion. This job did for me what starring in a reality television show and becoming known worldwide didn’t do: it made me feel good about myself. Having responsibilities, new skills to learn, and a creative outlet allowed me to slowly start coming alive again.”

Several of Hefner’s girlfriends and Playmates were able to launch successful careers—but only after they escaped from Hefner’s orbit and his intentional attempts to disempower them. Holly takes college classes, as well as other continuing education courses, during her years in the mansion. When she is finally able to persuade Hefner to allow her to work as an intern, producing content for Playboy magazine, her innate confidence returns from the dead. This exemplifies Holly’s commitment to Personal Growth Despite Severe Resistance.

“‘Because the show is about Hef’s girlfriends, I feel like I’m signing a contract being a relationship,’ I whined. I was beyond frustrated. I had my back against the ropes. If I wanted to move forward with the show for a fifth season, I had to bind myself to Hef’s production company. What if I wanted to move out? Or do another show? I felt like this contract might make that impossible.”

The Girls Next Door television program proves a financial lifeline for the struggling Playboy Enterprises. The popularity of the three girlfriends means that Hefner, who only occasionally appears before a camera, knows he must keep them under contract if he is to continue the popular, lucrative program. He slyly presents them with restrictive contracts, which he demands that they sign immediately. Even as the women’s fame and confidence in their abilities grow, these contracts enable him to keep his girlfriends under his control.

“I had never cheated on Hef. He had slept with an army of different women during our time together, but I remained faithful. Despite all my insecurities and regardless of how desperate I was to have one night out, in my mind I was still in a relationship and I was nothing if not loyal.”

During Holly’s seven years in the Playboy Mansion, she respects Hefner’s nightly 9 o’clock curfew. Hefner never allows her to travel anywhere without either a chaperone or security. On the one occasion when at last she travels to Las Vegas for work, and has an innocuous dinner with a man, she discovers that Hefner has secretly had her followed. His intention was to have something to use against her: to make her feel guilty and reinforce his control.

“Seduced by this good-looking man who was seemingly frantic in his affections for me, I allowed myself to be lured in. After knowing each other for only a few months, he needed me by his side for the world premiere of his new show. I was the one who calmed his nerves, he said. I had become so used to taking a backseat to Hef and sharing the remaining spotlight with other women, I was beyond flattered that this successful man was so enthralled with me—and only me.”

At first, Criss Angel seems to be the opposite of Hefner. He does not have a stable of girlfriends and claims his sole interest is in settling down with Holly. Before long, however, she begins to realize that Criss is just as controlling as Hefner. Criss wants her present with him constantly, controls all of her movements, berates her with angry outbursts, and seems on the verge of becoming violent. Whereas she was simply able to move out of the Playboy Mansion when she pleased, she must surreptitiously escape from Criss.

“While I had long ago tired of Hef’s double standards, ridiculous rules, and belittling comments, this was the first time I really realized what a manipulator he was. Suddenly, it all became clear to me. The biggest reason I never got along with most of the girls in the house was Hef. He encouraged the infighting all along, despite his fake pleas for harmony. He was looking more and more pathetic in my eyes. I couldn’t believe I had been manipulated for so long.”

Holly sounds here like someone who is recovering from life in a cult: like a true believer who finds out that the convictions they have treasured for years were false all along. She at last recognizes the full extent of Hefner’s duplicity in manipulating her and so many other women throughout involved with Playboy. At every step, Hefner was insincere. He was powered by his ulterior motives—his own personal aggrandizement and desire for financial profit—not by any real enjoyment of or love for the women he worked to so hard to keep close.

“I felt like Hef was trying to sabotage me in Los Angeles by bad-mouthing me and leaving me out of Girls Next Door-related press, and now Criss was trying to banish me from Las Vegas.

Sorry, boys, it’s not going to be that easy, I thought, pulling my hoodie over my head. […] You haven’t seen the last of me.”

As Holly works to develop several entertainment projects, she learns that both Hefner and Criss are actively attempting to sabotage her. Both men are furious that she has walked away from her romantic relationships with them. At the time, Holly felt attacked and belittled. Yet the hostility of these two established, powerful male celebrities was a twisted compliment: They perceived her as important enough to merit their cruelty.

“As the youngest headliner on the Strip, I took the city by storm. I knew that promoting myself was the key to having a successful run with Peepshow, so I attended every opening, every red carpet event, and every pool party, and landed myself on the cover of all the Vegas entertainment magazines before my debut. Despite the crumbling economy, it was a magical time in Las Vegas. Somehow it seemed that the city was extra determined to carry on just as fabulously as it had before.”

After multiple auditions, Holly wins the role of the lead entertainer in the traditional Las Vegas burlesque venue, Peepshow. The production is unlike anything that she has ever done before, and she perceives it as her chance to excel on her own. The life she lives at this point is completely different from the reality of her previous seven years, during which she was cloistered, controlled, and highly criticized. In contrast, she is now surrounded by her own friends and able to move about freely. She finds her new context inspiring and uplifting.

“Like me, Marilyn had suffered at the hands of some not very nice men. She was used, underappreciated, and struggled to find herself. She worked her way up in Hollywood with stars in her eyes and a kind heart, but found that Hollywood wasn’t always as kind in return. She may have been publicly adored, idolized, and lusted after, but she often felt alone and trapped. Those dark demons eventually got the best of Marilyn. Part of me knows that could have easily been my fate had I not chosen to take care of myself. I only wish poor Marilyn could have done the same.”

Holly’s journey toward fame and acclaim initially began when she became fascinated with Marilyn Monroe as a little girl. Now a globally famous entertainer in her own right, Holly has the opportunity to try on items from Marilyn’s personal wardrobe. The experience revives her identification with Marilyn, but also compels her recognize the important distinction between them.

“It all sounds a bit dramatic, I know, but I had pretty much given up when in 2011 I finally met the man I would marry: Pasquale Rotella. Isn’t that how the universe always works?

[…] He was the total package and was also at a point in his life where he was ready for a serious relationship. […] This is an important note: a man has to already know what he wants. Don’t waste your time trying to change someone’s mind. It never works.”

After breaking off her relationship with Criss, Holly goes five years without a serious romantic relationship. She hints that she was pursued by a number of unsuitable individuals, whom she turned down because her experience with Hefner and Criss had taught her to be leery. It was only when she accepted the idea that she would never find the man of her dreams that she met and instantly fell in love with Pasquale.