Down The Rabbit Hole

Holly divides the Prologue into two scenes, which mirror her psychological development.

The first scene occurs in 1988, when she is nine. She receives a Marilyn Monroe paper doll book for Christmas, and subsequently watches all of Marilyn’s movies. Holly dreams of leading a glamorous life, like Marilyn’s.

The second scene occurs 14 years later, behind the Playboy Mansion’s gates. “Everyone thinks that infamous metal gate was meant to keep people out,” Holly writes, “But I grew to feel it was meant to lock me in” (4). Holly is depressed and suicidal. She wonders if she has the courage to die by suicide. Despite being Hefner’s main girlfriend, she is unsure that anyone would take note if she died. Holly decides to live so that she can write Playboy’s true story.

While a second-year student at Portland State University in Oregon, Holly auditions to be Playboy’s Millennial Playmate. She is inspired by the fact that Marilyn Monroe, her teen idol, was the very first Playmate. Playboy sends a tour bus to 45 cities across the US, photographing anyone who wishes to audition. Though she has signed a release, Holly feels surprised when asked to remove her bikini top. She asks the photographer not to distribute the photo unless she is a serious contender to be the Millennial Playmate. Later, she learns that the tour was nothing but a publicity stunt for Playboy’s Millennial issue. Its Playmates, a pair of Peruvian twins, had already been chosen. Holly never had a chance.

Shortly thereafter, Holly maxes out her credit cards to buy breast implants, hoping that these will finally make her feel secure about her appearance. She then moves to Santa Monica, California, to pursue an acting career; she also enrolls in Loyola Marymount University. Her coursework there is so demanding that she drops out after just one year.

Desperate for money to pay off her credit card bills, she works as a server for the Hooters restaurant chain and models for the Hawaiian Tropic^® skincare brand. At a party for models, Holly is approached by Hefner’s personal physician, who invites her to a Playboy Mansion pool party. All guests, he says, must wear sleepwear. Holly accepts his invitation and attends along with another Hooters server. Photographs are taken of all the women who attend. After touring the mansion grounds, she introduces herself to Hefner. She finds their meeting oddly anticlimactic.

Over the next year, Holly is repeatedly invited to the mansion’s Sunday evening pool parties. She writes, “It was unlike anything I had ever seen before—it was truly an oasis in the middle of Los Angeles and a life so unlike my own that I almost envied the women that were able to call this magical place home” (25). Holly grows close to several of Hefner’s seven girlfriends, particularly Vicky. Vicky allows Holly to see her room, and explains all the benefits of being a girlfriend. Unfortunately, Holly doesn’t realize that Vicky has ulterior motives in befriending her. As the year winds down, Holly’s two roommates announce their intention to move. Holly knows that she cannot afford their apartment by herself, but has no place to go.

Vicky invites Holly to attend one of the nightclub outings that Hefner and his seven girlfriends make twice a week. Uncertain about what will happen, Holly goes to the mansion and rides with Vicky and the entourage to a nightclub. The presence of Hefner’s group of young women causes a great stir. Holly feels swept away as they eat, dance, and drink a great deal. Vicky encourages her to get as close to Hefner as possible. At one point, Hefner offers her Quaaludes, joking that in times past they were referred to as “thigh openers.” Afterward, the group returns to the Playboy Mansion. Vicky informs Holly that, like the other girlfriends, she is expected to put on flannel pajamas and go to Hefner’s bedroom. Though Holly had been assured repeatedly that the girlfriends are not required to have intercourse with Hefner, she now learns that this is, in fact, expected of them: especially it they are newcomers. Holly has sex with Hefner for the first time.

Following this encounter, Holly falls asleep in Vicky’s room. In the morning, she searches for Hefner. Anxiously, she tells him she has nowhere to live and asks if she can move into the mansion since he is looking for a seventh girlfriend. He casually tells her, “You can stay for a while and we’ll see how it works out” (43).

Holly eventually realizes that Hefner values Vicky in large part because she recruits so many new women for his nightclub trips.

Immediately after Hefner approves Holly’s request to move into the mansion, she goes to the little apartment she was about to lose, gathers all her possessions, and returns to the mansion. The staff assigns her to a shared bedroom with April, another newly arrived girlfriend.

The timing of Holly’s move is fortuitous, occurring only a few days before the terrorist attacks on September 11, 2001. She feels safe within the mansion’s walls—much more so than she would have on her own in Los Angeles.

Holly is surprised to learn that the other girlfriends are not forthcoming about the schedule or rules for life in the mansion. Even so, she quickly discerns the requirements of her new life. She learns there is a chronological pecking order among the girlfriends, with Hefner playing the newest women against the older ones. She must observe a curfew of nine o’clock in the evening. She may not consort with any of Hefner’s paid employees. She must not use any illegal drugs. She cannot have an outside romance, since Hefner is supposed to be every woman’s only boyfriend (in actuality, most of the women have other boyfriends, although they have few lasting relationships due to the strictures they are forced to observe). In return for their obedience, Hefner gives each of the girls a $1,000-per-week allowance. Twice a week, they are expected to accompany him to nightclubs and engage in sex acts with him. They are also to attend social events involving Hefner’s friends. However, most of the girls find ways around this ostensible obligation; often, only Holly and April attend.

Holly continues to work for Hooters until the restaurant asks her to represent Santa Monica in their national Hooters Bikini Contest. When she excitedly tells Hefner of this invitation, he orders her to reject it. Despite her tears, he further demands that she quit working for Hooters altogether: He is jealous whenever her attention is on others. Holly obediently resigns.

Not long after Holly moves into the mansion, Hefner takes his entire entourage to a Comedy Central Friars Club banquet in New York City. As Holly becomes more familiar with the activities and the relationships among Hefner’s girlfriends, she discovers that much of what she had believed about Playboy is, in actuality, a facade. Most of the girlfriends are only with Hefner because they are angling for Playboy pictorials. Those who achieve this goal almost always leave the mansion shortly thereafter, in pursuit of their own entertainment careers. Their intimacy with Hefner is purely transactional.

Holly is likewise distressed by the underhanded treatment she continually receives from the “Mean Girls.” In their eyes, she is less sophisticated and attractive than the other girlfriends. Consequently, they ostracize her and make her the butt of their jokes.

Within six months of Holly’s arrival, Hefner’s then-main girlfriend, Tina, appears in a Playboy pictorial and abruptly moves out. Afterward, Hefner unceremoniously asks Holly to be his new main girlfriend. His request is briefly rendered moot when Tina briefly moves back into the mansion—just to show that she can resume the place with Hefner that she feels she deserves—only to rapidly leave once again. Holly thus becomes Hefner’s main girlfriend.

Holly finds the experience of being Hefner’s main girlfriend unlike anything else she has ever experienced. Nothing has prepared her to be in a romance with a man old enough to be her grandfather. Moreover, Hefner is a mass of confusing emotional contradictions. On the one hand, he professes his love for her regularly. On the other, he berates her often. He treats her more like a teenaged daughter than a girlfriend, and “mansplains” to her constantly. When she moves into his bedroom, she discovers that she has less space for her possessions than she had in the small private bedroom she occupied after moving out of April’s room. She nicknames her space Hefner’s suite “the vanity,” since it is only one corner of one closet.

Her promotion to main girlfriend also worsens her dynamic with the other women. On the surface, they treat her with feigned respect, give her gifts, and compliment her. In reality, though, they utterly detest her.

These events take their toll on Holly’s self-esteem. She writes, “Prior to moving into the mansion, I’d been a fairly confident person, but it didn’t take long for my self-worth to start to crumble” (68). In an effort to improve her appearance, she works up the courage to ask Hefner to fund a nose job. When a new young woman arrives with hair as long as hers, Holly decides to change her appearance, cutting 20 inches off her long hair, dressing like Marilyn Monroe, and putting on red lipstick. Hefner is aghast by Holly’s style experiments. He warns her never to wear red lipstick or try her “Monroe look” again.

Just as Holly begins to feel that she has lost herself and has no honest, trustworthy source of companionship, she meets Bridget: a new attendee at Hefner’s pool parties and, eventually, one of his girlfriends. In Bridget, Holly finds a true friend, one with whom she can speak candidly about the surreal realities of Playboy Mansion life.

Holly’s relationship with Vicky—who had initially appeared to be her friend—is deteriorating. Now that Vicky has realized that she will not persuade Hefner to give her a Playboy pictorial, she is becoming increasingly bitter.

One day, Vicky visits Holly’s room, fuming about girlfriends who became centerfolds despite being newer additions to Hefner’s entourage than Vicky. Vicky also mentions that wealthy procurers are approaching Playmates and girlfriends. They are offering large sums of money—far beyond what Playboy gives the women—to travel the world as elite sex workers. Vicky asks Holly whether she would be interested in doing such work. Holly quickly refuses.

Vicky is so put off by this response that Holly realizes Vicky’s intention was to recruit her into sex work. Holly relates that several Playboy Playmates eventually worked for an organization called Nici’s Girls, which connected them with extremely wealthy Turkish clients that employ the Playmates as sex workers. Hefner had learned what was happening, but shut down his investigation into Nici’s Girls for fear that the media would report it, damaging Playboy’s image as a legitimate magazine and organization in the process. Hefner seemed unaware that Vicky was recruiting sex workers from among his girlfriends as well as Playmates.

Vicky also devises a scheme to invite outsiders to Playboy’s invitation-only parties by having the girlfriends charge them for an invitation. When Hefner confronts them, Vicky and the girls who participated in her scheme have Playboy tattoos permanently inked on their ankles, then come back to the mansion to demonstrate their renewed loyalty to Hefner. When Hefner decides that he will kick Vicky out of the mansion anyway, Holly rejoices. Even so, she feels pressure to appear outwardly unemotional.