From the Bunnies' Mouths: How Hugh Hefner Seduced (Very) Young Women

Ever wonder how 82-year-old Hugh Hefner was able to simultaneously seduce the 19-year-old Shannon twins and have a large number of age-gap affairs over the years? Before we get to the twins, let’s start with Izabella St. James.

Izabella St. James wrote in Bunny Tales Behind Closed Doors at the Playboy Mansion that she first saw the 74-year-old Hugh Hefner when she was in her early twenties at the Sunset Room in Hollywood and was “[...] intrigued by Hef and attracted to him […]”. While Hef was surrounded by a bevy of beautiful young women, Izabella went to say hello. Consequently, Dr. Mark “Doc” Saginor, Hefner’s physician and friend, invited Izabella to sit in Hefner’s booth. 

Hefner & Izabella St. James

Izabella said that Hefner was very polite, very sweet, had a warm smile, and he made her feel welcomed and relaxed. After drinks, Doc asked Izabella for her phone number and invited her to a “Fun in the Sun” party at the Playboy Mansion that was subsequently followed up by invitations to other parties at the Mansion.

Approximately a year after Izabella returned from studying abroad in Poland, she ran into Hefner on Wednesday at Las Palmas and on Friday of the same week at Barfly. After she went over to say hello, Hefner invited her to join him and his entourage the following Friday, which turned out to be a recruitment session. 

At the club on the following Friday, a number of Hefner’s girlfriends told Izabella “[…] how much fun they were having, how much money they made, and what a great opportunity it was to live at the Mansion.” 

Furthermore, they told Izabella that Hefner was “interested” in her and that she should consider being one of his girlfriends. However, when Izabella was told about “the bedroom”, she wrote I “[…] went home as fast as I could.” (Note: We'll elaborate on “the bedroom” below, but for now, "the bedroom" was where, after taking a Viagra pill and lathering in baby oil, the girls took turns “riding” Hefner after he had been serviced orally.)

Hefner was persistent, and he invited Izabella out on several more occasions. She accepted his invitations, and that was when she began to be “[…] seduced by the Playboy lifestyle. The private jet, the parties, the limos, the Grammys, and the carefree lifestyle […]”  Eventually, Izabella and Hefner had a bitter breakup, which may explain why Hefner changed his seduction approach with Kendra Wilkinson.

Kendra Wilkinson wrote in her memoir, Sliding into Home, that after she posted her photograph on One Model Place, the initial call she received from Playboy was to ask her if she wanted to be a “painted girl” (i.e., nude waitress) at Hefner’s 78th birthday party. 

She received another call two days later informing her that Mr. Hefner saw a photo of her and wanted to call her personally. And what did the almost 80-year-old Hefner say when he called the 18-year-old Kendra, “I look forward to seeing you at my birthday […] Also, I’d like you to consider being my girlfriend.” 

Kendra Wilkinson & Hefner

After meeting Hefner for the first time, Kendra wrote: “He was very charming; he had a powerful way about him […] he was just so cool. The way he acted and the things he said were unlike anything I had seen or heard.” 

In addition, Kendra loved the fact that, despite the bevy of beauties surrounding Hefner, he kept looking at her and they kept staring at each other. 

At the end of the night, Hefner gave Kendra a key, asked her to spend the night, and inquired, “Will you be my girlfriend?” Kendra wrote: “There was only one thing I could say: ‘Umm, okay.’”

Why did Kendra say yes so quickly? Well, she wrote that their age difference was not a factor, nor was the fact that Hefner already had, not one girlfriend, but “ten times more girlfriends than most”, but it was because Hefner had boosted her self-esteem, he was “a true gentleman”, and he was trustworthy. 

Holly Madison provides another view of Hefner in her best-selling book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. Holly wrote that when she met Hefner: “He had the “nice guy” act down pat and it worked [...] he had a certain swagger. There was a gentlemanly air about him [...]” However, Holly wrote that to reduce the high turnover rate of girlfriends, Hefner started keeping his girlfriends “broken and needy”. 

Holly Madison & Hefner

Holly wrote: “I found myself constantly trying to compete with the other girlfriends who were all caught up in who was prettiest.”  And she opined that: “It was in his best interest to have us wallowing in our own insecurities and pawing for his acceptance. Girlfriends that didn’t get along gave him the feeling of being fought over—and being fought over made him feel desired [...]”  

And how did the girls try to gain Hefner’s acceptance? Holly wrote: “When he would compliment a girl on a particular dress, pair of shoes, or even the way she wore her hair, we all felt the need to replicate it for our next evening out.” 

Allegedly, Hefner particularly liked to pit the old(er) Bunnies against the young(er) Bunnies. Holly was advised by an old(er) Bunny:

“He always plays the oldest one against the youngest one,” Vicky explained, eager to share her expertise on the topic as we gossiped about the situation. “Tina may be his main girlfriend, but she’s older, so he likes to play on her insecurities by playing favorites with whoever the youngest one is.” 

Consequently, Holly shared that she started wearing clip-in extensions to give her “the long hair Hef preferred.” Furthermore, Holly wrote that Hefner: “[...] was obsessed with women looking as young as humanly possible.” 

Holly even wrote that Kendra confessed: “I’m very insecure right now about my face. I get scared with Hef looking at me at the mansion and maybe thinking I’m ugly.” 

Interestingly, Holly related that Kendra “had already hooked up with Hef” prior to him asking her to be his girlfriend.” Holly alleged: 

“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."

As for "The Bedroom", Holly shared some details about her first orgy slash initiation with Hefner:

As Tina led me into the bedroom, I stumbled over and weaved through massive piles of junk covering the floor. It appeared that Hef liked to collect more than just women. Ceiling-high piles of videotapes, stuffed animals, art, and gifts littered the room. It was like an episode of Hoarders. But perhaps in his case it would be more appropriately titled Whore-ders. Two huge television screens projecting graphic porn lit up the otherwise dark bedroom. In the middle, a very pale man was tending to his own business (if you’re catching my thinly veiled innuendo) and puffing on a joint before passing it around to the nearest blonde. 

The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed—some kneeling, some standing, and some lying down. I sat myself on the edge of the bed—unsure of what to do next […] My eyes had adjusted to the darkness and I could see that all the girls, backlit by the large screens, were putting on a show: […] they were getting it on or making out with each other [...] The girlfriends, and Vicky, it seemed to me in particular, were desperate to bring as many new girls up into the bedroom as possible […] “Heeeef . . . don’t you want to be with the new girl?” 

Vicky screamed over the loud music as she reached over and pushed him towards me. Much to my surprise, my turn was over just as quickly as it started. By the time I was able to wrap my head around what was happening, Hef had already moved on to Candice, then to a few of his actual girlfriends before finishing off by himself, as he always did […] Some of the girls leaned over and quickly picked Hef on the cheek […] The girls began filing out of the room, offering Hef a few candy-coated “good nights.” 

Quickly, I pulled on my pajamas and followed Vickey down the hall and into her bedroom […] Vickey ordered cheeseburgers and fries to the room as if it were any other night, but I passed out before the food even arrived.” 

Holly went on to write that: “Most of the girls that ended up becoming girlfriends reacted the same way: they were very nonchalant about their “initiation.” 

Thus, from the three former Bunnies we can cull the following about Hefner. He was:

very polite

very sweet

warm

welcoming

persistent

powerful

cool

attentive

direct

possessed a certain swagger

had nice guy "act"

pitted bunny against bunny

played on insecurities; and he was

charming

As for charming, in The Charisma Myth, Olivia Fox Cabane divided charisma into three main categories: 

Presence Charisma – you should be in The Now and avoid constantly thinking and/or worrying about the past or the future 

Power Charisma – you should have power [over yourself] (i.e., self-control)

Warmth Charisma – inwardly you should have high levels of self-esteem, 

self-confidence, and self-compassion. And outwardly, you are altruistic.

In terms of power and warmth charisma, we know from Kendra that Hefner had “a powerful way about him [...] he was just so cool.” And we can infer from Izabella, Kendra, and Holly that Hefner exuded presence charisma.

And per the Pickup Artist community, there are at least nine ways for men to approach (young) women:

Direct: “You’re beautiful!”

Indirect: “Can I get your opinion on something?”

Guerrilla: “I want to make love to you. Immediately!”

Inebriate: “Here, have another drink.”

Trite: “Is that a mirror in your pocket, because I can see myself in your pants.”

Open: “I’m the prize. Ravishing women will desire and approach me.” 

Arranged/Inner-Circle: “Your cousin’s a cardiology intern and lives in the Village - with no roommate!”

Wine and Dine: “I have a huge loft in SoHo; so, I usually take car service and park my black Porsche in the garage on Prince Street.”

From Bunnies’ Mouths, we see that, combined with being charismatic, Hefner used a combination of the Direct, Guerrilla, and Wine and Dine approaches to seducing young women. 

The Shannon Twins & Hefner

And as for the 19-year-old Shannon Twins, Karissa and Kristina said that 82-year-old Hefner simply sent them an invitation to be his girlfriends and move in - via snail mail!

The Girls Next Door | Season 6
82-year-old Hefner & 19-year-old Shannon Twins

On The Girls Next Door “Meet the New Girls” episode (s06e01), the Shannon Twins said:

“We tested for Playmate in Miami, and then got a call to come and test for the 55th anniversary Playmate at the mansion, and we met Hef.” 

“He liked us. So when we left, like three weeks later, he sent us a letter saying he wanted us to be his girlfriends and we moved in.”

In the end, we would imagine that, in hindsight, à la an Arab prince, Hefner would have opted to marry up to four young Bunnies instead of cycling in and out of ultimately grumbling girlfriends.