What I Learned About Men From Working For Playboy

Today, very few people know that my first “real job” was being a Bunny at Playboy. So many people that do know have begged me to write about it… curious what it was like. So I thought, “why not”?

Hefner is worth studying for those who don’t remember him, the founder of the Playboy Magazine and the Playboy Clubs. Hef’s idea was to support women’s sexual freedom and showcase his vision in the clubs and magazine.

He defied repressive social and sexual attitudes of the 1950s by insisting that men could make martinis, talk about jazz, and want women. And women in the pages of Playboy could have sophisticated interests and pursuits, including sexual expression. Those were not mainstream ideas until much later.

Playboy had a “type.” It came to be known as “Bunny image.” It was a clean-cut “girl next door” that also could project a subtle, steamy sensuality. Playboy was far more understated than the magazines that followed, like Penthouse and others. In the earlier days, the centerfolds did not even show pubic hair.

The Playboy empire is dead now, with even the popular magazine shutting down in 2020. Playboy was a product of a time that had gone by: before the Women’s Movement, before XXX-rated magazines, and certainly before XXX porn everywhere on the Internet.

Few men impacted our social landscape of the 21st century more than Hugh Hefner. As a result, the Playboy Bunny logo is one of the most recognized logos globally, third behind Apple and Nike.

Hef was loved by many and hated by many more. Still, whether you see him as a champion of sexual liberation and civil rights for women or a chauvinist who proudly objectified us, you can’t deny that Hefner was an innovator.

Hugh not only broke into one of the most challenging industries in the world, but he did so by revolutionizing the conversation about sex that our society was having. Sex has always been one of the most taboo topics here and in the world. When he created this empire, his unique “take” was his belief that women should be celebrated for their sexuality, not condemned. That was revolutionary at the time and is still challenged to this day.

So how did a small-town farm girl end up THERE?

I grew up in rural Colorado. I was as naive and innocent as a girl could be, having spent my entire youth with my horses and dogs and an occasional baby cow.

I went to the University of Colorado Boulder after high school. It was my first exposure to people of color, people from all over the world, black power, the women’s movement, and assorted protests against the war.

Playboy International had staff photographers who would frequent college campuses and any other place young women could be found. One of them recruited me and suggested I go for a “test” at the Club in Denver. I was intrigued but had only worked part-time at a Campus bookstore. So I knew very little about life, myself, or the world I was about to enter.

My first impression was that it was all very glamorous. Those many decades ago, stepping into a Playboy Bunny outfit felt like the closest a small-town girl like me could come to celebrity status, and it was very heady! There were movie stars and entertainment stars that orbited around the Playboy Clubs, in addition to the promotional shoots we did. The training was rigorous; the shoes were murder, and the bunny suit was flattering and fun. I was excited about the opportunity, but the real benefits I got had nothing to do with a cute costume or ears and a tail.

After the rigorous training period, we had to select the area in the Club where we would work. Playboy Clubs were, for many decades, the upscale version of Hef’s Magazine. The City’s movers and shakers frequented the private clubs. It was the destination of choice for men to impress business associates or bring their wives and girlfriends. In addition, there was the Penthouse dinner showroom, the Living Room, the Playmate Bar, and the Gift Shop. I quickly figured out the most money would be in the Penthouse dinner showroom, so I worked there first.

I was highly motivated to learn how to earn good money. I saw my mother struggle to survive with an 8th-grade education and two little kids to support. She finally gave my brother to my uncle as she could not afford to feed us both. Before I got out of grade school, I learned in a poignantly personal way that if I was EVER to have any freedom, it would need to start with financial freedom. Becoming financially independent became a lifelong quest.

I was so dedicated to this drive to independence that I spent 25 years as a divorce financial analyst, helping other women not go broke after divorce. I cannot overstate how important this decision to pursue financial independence was, which shaped my career path so early in life. And Playboy was my entry into that possibility. The most profoundly important thing I took away from this experience was that my mindset was changed forever regarding money and earning, and it has served me well my entire life. There is only success in any area of life with the belief that you CAN. Whether you believe you can or cannot, you will be right.

As I began my new career as a bunny, I had to learn how to be charming and friendly no matter what. You could never have a bad day or a bad mood while on the floor. Likewise, Keyholders expected to have a pleasant atmosphere when visiting. At first glance, it would seem like Playboy Clubs were the epitome of male pleasure, and although they seemed to enjoy the Club very much, make no mistake: WE held all the power. There was only one thing that made a Playboy Club any different than any private club in the world: people joined because of BUNNIES. What could I make of this opportunity?

I was curious initially that some of the girls were big earners while others were not. What was the difference between them? Indeed, the area of the Club you worked in determined some of that, but I wondered, what was our job REALLY?

One day one of my colleagues, Brianna, got selected to be a Centerfold in the magazine. When you are chosen for Centerfold, you are on contract with Playboy International for a year and travel to promote the Magazine and the Clubs. Brianna approached me and encouraged me to take her job as the “pool Bunny” shooting bumper pool at the end of the Playmate Bar.

I wasn’t interested as I was doing very well in the Penthouse. But she insisted that I shouldn’t miss the opportunity. So, sensing she knew something I did not, I followed her advice and became the pool bunny.

What was a day in the life of a ‘Pool Bunny?’ I got a bag of quarters to release the balls for play. I was obligated to turn $17 into the house at night; anything beyond that I could keep. It was $1 for a customer to play a game with a Bunny. I could see no possible way to make anywhere near what I was making in the Penthouse playing pool at $1 a game.

Bumper Pool is a quick game. After playing many games a night, I developed mad bumper pool skills. I started to realize that nobody could beat me unless I let them. Here is the first significant life lesson I learned at the pool table:

I thought my goal was to earn as much money as I could. Although that is a good goal, something was even more critical here. I learned that if I could run the table in about 60 seconds and then carefully study my opponent’s face, I would know in a second how to proceed. Proceed to what? To understand quickly who was standing in front of me. My “spidey” sense of reading people was developed to a large degree because of this experience.

Most men figured out they couldn’t beat me after I beat them quickly. However, I could see that it was mildly upsetting for some of them, so naturally, I let them win. I let them win repeatedly, and they were thrilled that they “conquered the pool Bunny.” But actually, I had conquered them in another way: I took ALL their money. After playing several games, they would leave me $100- $200, so I was happy to let them win all night.

The other kind of guy totally got off on the fact he couldn’t beat me, so I beat him over and over. The looks on the face of pure delight when I would beat them badly was intoxicating. I’m pretty sure my love of cuck torment started right here.

My ability to “read” these guys then deliver an experience that would cause them to enjoy the time with me paid off. Big time. How valuable would it be for every person to learn early in life how to read other people’s faces and energy? That tangible gift was one I couldn’t appreciate at the time, but has served me brilliantly all my life. I have Playboy to thank for that.

You see, I learned very quickly what my job actually was. It was irrelevant who won the game. Who cared who won this silly game? My job was not to be the best bumper pool player in the land; it was to deliver an experience to these gents that would allow them to have as much fun as possible. That was my only job. Quickly determine the state of their ego, then provide the thing they would enjoy most. That lesson has served me so well over decades, working in a very male-dominated profession. I learned that being charming, smiling, and gracious is the best way to wrangle the male ego and keep all the power. :-) Smart, confident men don’t even care that you have it. It is only the very insecure man that is threatened by strong women. So although I continue to practice being gracious in my life every day, I reserve a healthy cynical snark for my close friends and to share on social media selectively. Being able to laugh at myself is pretty important.

I was still at the Club when the Women’s Liberation movement was starting. Gloria Steinem (famous feminist author and activist) exposed her take on Playboy when she worked as a bunny for 3 weeks. The women’s movement went to war with Playboy and other institutions that were built on objectifying women. I’ve always considered myself a feminist, but these attacks on Playboy got me thinking deeply on the issue. Are we exploited?

Absolutely how we looked and behaved mattered. But was I used? Or was I using them? I don’t think those are the right conclusions. Of COURSE, we were objectified. Absolutely that turned into big bucks for many of us. Who was using who? I prefer to think of it all in different terms: The truth is that Bunnies and the men who came to look and interact with us had a symbiotic relationship. They expected to enjoy their time in the club and I expected to make a living. I in no way felt taken advantage of or exploited at any time at Playboy. The other gifts I took from this experience so far outweighed those who loved to criticize, and I learned quickly to ignore the carping of critics.

The trouble with the “exploitation” angle was that I was bringing home upwards of $1500 cash a week playing pool, so I promise you I did not feel “exploited.” I earned more than many of the executives who frequented the Club. That was a lot of money back then! One of the most important lessons was that, as a female, I could make serious bank. It changed my belief system: "I’m capable of earning big and making my way in the world.” It gave me hope I would not end up like my mother. What a fortunate belief system to develop early in life! I’ll always be grateful to Playboy for delivering that.

Believing in myself to navigate an environment, take advantage of the opportunity I found, and feel like I had to make no excuses for any of it felt like freedom.

If I’m really transparently honest, feeling power over men was as addictive as heroin.

My first career path did so much for me: it solidified my confidence, taught me how to earn, showed me the value of being friendly and pleasant in every situation, and gave me a slight “edge.” I’m happy to report I’ve learned to enjoy male torment in ways I couldn’t have imagined back then. Is it any wonder I’d end up as a cuckoldress?

Life is good, and I’ll always be thankful for my experience at Playboy and what I learned there.

Exploring the crossroads of personal growth, spirituality, business chutzpah, love life, and why your kale smoothie tastes like grass. Life’s too short for boring reads and unseasoned tofu. Hit that ‘subscribe’ button for wisdom with a side of whimsy. https://medium.com/@grace.tinsen

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