Let us keep in mind: he was the most housebound of all despots, hermetically sealed indoors, pale, working (and playing and romancing) at home like no one in history at this point, the first and foremost fully embedded man of Mansion Life. He holed up through most of the sixties in a brown and gray Gothic structure on Chicago’s Gold Coast, in the most fabled of all urban domiciles, the original Playboy Mansion, 1340 North State Parkway, Valhalla, Sodom, Gomorrah, James Bond Heaven, etc. Basically, he went nowhere and had the world come to him. Then he started to make his TV show in California, and then there was Barbi on the set, and then love, and then the pallid one made some changes. Just for her. She threw him into sunshine, made him play tennis with her—on public courts!—and made him pedal bicycles with her around Los Angeles. This was not him, but it was him, giddily so. Never fond of travel, he suddenly found himself traveling the globe with her. He was smitten and traveling was part of the romantic pursuit.
One trip to Acapulco: They lay on the beach and saw people parasailing in the skies. She said, “Oh, that looks like fun!” He said, “Let’s go do it!” He had never been able to swim. Let’s go do it! She went first. He went next. He flew over water for her and landed safely, and remembered only then that he could have drowned. Just for her. “I would have gone without a life jacket if Barbi hadn’t urged me to put one on.” And she would recall, “I guess Hef is a little crazy when he gets into something. We were both like little kids with each other.”
All of which is to say, anything is possible where love is concerned, even among the most unyielding of us.
When You Work with Them, You Can’t Not Notice Them
Sex in the workplace is here to stay, because that’s where most of us spend so much of our time: Common interests in a common location make sexual communication and activity a certainty.
But a romance in the office can be a complicated affair in today’s world, with accusations of sexual favoritism, harassment, or worse. So handle the personal part of your professional life with a reasonable amount of care and discretion. It is always important to make certain that you aren’t misreading the signs of interest or uninterest in a coworker in matters of a romantic nature. Before a professional relationship can turn into a personal one—whether casual or serious—you need to be certain of the other party’s interest. And you need to be concerned about the rules of engagement that may have been established in your company and the attitudes of your coworkers as well.
If you have properly weighed the considerations and consequences involved, there is little to be gained by considering all office-related romances out-of-bounds. Life is short and love conquers all. Or at least that’s the way it should be.
Before he eschewed office life for the velvety cocoon of Mansion mooring, he fraternized most insatiably with females in his employ: “Offices are where you meet members of the opposite sex,” he would say matter-of-factly. His directive in personnel matters was nondiscriminatory from the start. “Everyone was to be judged on ability,” said one early human resource head. “But if I had a choice between two equally qualified people, I hired the more attractive one.” Playboy receptionists therefore tended to be stunning. Upon hiring dusky Bobbie Arnstein, who would become his closest aide-decamp and private secretary in the sixties, he leaned over her desk and instructed, “Don’t think of me as your boss or the publisher of this magazine. Think of me as a guy looking for a date.” She thought of him both ways and liked it just fine, as did he.
When She Is Jealous, Tenderly Try Telling the Truth
I have gone out of my way to minimize the downsides of jealousy through being open and honest in my relationships. Jealousies come out of the hypocrisy and lies of deception.
Then again, I get a pass that other guys don’t, since women’s expectations of me are different. It makes it easier because all of my cards are on the table.
Your Heart Can in Fact Be Suddenly and Happily Split in Two
There’s no question that it’s possible to be in love with two women at the same time. I’ve been there.
Another mermaid sighting in the Chicago Mansion’s Underwater Bar.
Indeed, he has been there on the scale of French bedroom farce, except that rather than dashing in and out of pastel parlor doors, he would hop aboard his private black jet, the one christened the Big Bunny, shifting heart and libido between the Playboy Mansions in Chicago and Los Angeles, in each of which he had ensconced a separate and distinctly different Very Special Lady. He wryly called this adventure his Captain’s Paradise, after the 1953 film Captain’s Paradise, in which Alec Guinness steamed between the ports of Gibraltar and Tangier, in each of which he had ensconced a separate and distinctly different wife. This went on, most breathlessly, from May 1971 to February 1974, beginning with the arrival in Chicago of a new Playboy Club Bunny in training named Karen Christy: “A big-breasted, voluptuous, baby-faced blonde from Texas who had stepped right out of my erotic, pre-code Busby Berkeley Hollywood dreams from boyhood.” (To wit: He saw in her traces of both his favorite platinum retro screen siren, Alice Faye, and the space minx Dale Arden—a heady and deadly Hefnerian yowsa combination.) She caught his eye instantly upon entering his world or House, and they made love on the big spinning Round Bed within several hours of meeting. “It was much more than lust at first sight,” his friend and colleague John Dante would recall. “Romance was foremost on his mind. In the end, he cared about her as much as he did for any love of his life.”
With Karen Christy on Movie Night at the Chicago Mansion.
Problem was: There was Barbi, for whom he did care as much as he did for any love of his life. Not only had she scouted out the property that was now the Playboy Mansion West, she was the reigning first lady of said Shangri-la. With the acquisition of his soon-to-be-legendary California estate and the ascension of Barbi three years before, he had subdivided his life, keeping tabs on his magazine and empire business in Chicago while reviving himself in the arid Western breeze, accompanied by the twinkling brunette coed who had stolen his high school retentive heart. But now, suddenly, here was this sultry, busty, and sexually playful blonde living in his own hometown Mansion, in his own hometown bedroom, with him, while Barbi roosted in his own West Coast lair, knowing nothing of what had developed in Chicago. And had continued to develop. He quickly began bestowing tokens of love, one after another, on Karen Christy, perhaps to ameliorate the fact that the world already knew of Barbi, perfectly sunny and telegenic media accoutrement that she was. Thus Karen, the sweet and easygoing country girl, received, according to legend, a diamond watch, a full-length white mink coat, a diamond Tiffany cocktail ring (for her twenty-first birthday), an emerald ring, a silver fox jacket, a painting by Matisse, a Mark IV Lincoln, and even a Persian cat. Quoth Hef: “A painting by Matisse? I think I’d remember that. It makes a good story, and someone once said if the life doesn’t live up to the legend, print the legend.”
For her part, she outdid herself making him feel loved: As a self-acknowledged romantic fool, he had become fond of a pop tune called “Tie a Yellow Ribbon ’Round the Old Oak Tree” upon his return from one lengthy Los Angeles trip, Karen had tied yellow ribbons around the branches of each tree in the Chicago Mansion front yard. He was and would continue to be a sucker for such gestures. But he would never forget that act in particular.
“I was rather crazily in love with them both,” he said later. “I selfishly recognized that if I had a combination of the two of them—Barbi and Karen—I would have the perfect girlfriend. Barbi was a Jewish princess: materialistic, career-oriented, but faithful and ideally adept in social scenarios. And Karen was devoted to me, had the common interests, enjoyed playing all the board games I loved to play, and had no aspirations to a career—no aspirations other than just to be devoted to me.” If he had to choose one to live on a deserted island with him, he noted, he would have chosen Karen—no public outings there, after all. But he would never live on a deserted island.
So now and then
one of them would visit the other Mansion—Barbi to Chicago, Karen to California—and the business of hiding Karen’s stray white bobby pins became an obsession, and whenever Barbi found a white bobby pin, it was an object of grim curiosity. And then, in the autumn of 1973, Time magazine photographed him in California with Barbi and in Chicago with Karen. Which revealed to Barbi that something was up. “I was, in effect, ratted out,” he would say, “and everything came to a head in momentous showdowns with both of them.”
Barbi left immediately. He begged her to return. She did eventually, while always thereafter maintaining an apartment of her own in Los Angeles, just in case. Karen stayed until she could no longer. She knew Barbi had returned to Mansion West, knew that his excuses and platitudes had grown thinner than air. When she left Chicago, he realized that he had no further need for Chicago life. He went back west, for the most part, and stayed there, stayed even after Barbi could wait no longer for commitment from him. And that was when she left as well, eight years following her pronouncement that she had never dated anyone over the age of twenty-four. Not that they stopped loving each other. Not that he stopped loving either one of them.
The Nevers of Love—Pay Attention
Don’t make a pass at another woman while in the presence of your date. It’s demeaning to you and to her as well. If a guy hit on a girl in my company, I’d say something about it. But I don’t tend to have that problem. As Jimmy Caan once said, “You don’t mess with the sheriff’s girl.”
There Is No Shame in Showing Your Tears
When a woman cries, you console her and sometimes you cry with her. The ability to keep those emotions close to the surface is a very good thing for all of us. The notion that men don’t or shouldn’t cry is naive. Men can and should.
A special moment with Special Lady Shannon Tweed.
Frank Sinatra could never quite fathom what Hefner had created for himself. Sinatra wooed like few others in human life, and rarely failed to get that which he wanted, female-wise, and all else–wise. But now there was this Hefner cat, with the big house in Chicago, which was Frank’s kind of town, and in this big house were all these chickies, and they all loved Hefner just a little too much for Frank’s taste. Frank was puzzled, but appreciated the chickies that he saw before him and those spread on Hefner’s magazine pages, too. Hefner, a swell enough fellow, visited Sinatra on a movie set in Miami in 1959, and he had this fantastic broad with him named Joyce Nizzari, and Frank made a play for her, at first unbeknownst to Hefner. (Hef grew up listening to, and aspiring to, the power of Swoonatra: “His songs supplied the words and music to our dreams and yearnings…. Sinatra really was the voice of our time.”)
He threw a party for Frank a few years later at the Chicago House, and Frank drew a bead on Hef’s latest girl, Joni Mattis, who would later become Hef ’s key social secretary but was at that point simply Hef ’s latest girl. Frank moved in on her as well. “Actually, he hit on her because she was my girlfriend,” Hefner would recall. “He was troubled, I learned later, by the fact that I had all the girls. Of course, if someone is going to try to hustle a couple of your girlfriends, it might as well be Sinatra.”
The two preeminent swingers of the twentieth century engaged as such, in tender combat over female flesh, and both could only shrug when it was over.
Striking Out Is Actually Good for You
We all fail from time to time, and that’s not a bad thing. There are going to be women who say no. The possibility of failure adds something to it. If every woman found you desirable, that would be pathetic. If it were a certainty, how boring life would be. It’s the adventure that makes it worthwhile.
It’s Over When You Know It Won’t Hurt You to End It
A relationship is ready to end when those special feelings disappear and you’re simply going through the motions. When the relationship no longer feeds or fuels you or the other person, but instead becomes hurtful, unpleasant, or meaningless. It isn’t fair to you or the other person to go through life like that.
But It’s Better to Remain Friends, No Matter What
Sometimes people wind up so hurt and disillusioned at the end of a relationship that they end up hating each another. But they pay a very dear price for that. If you loved them once, there must still be qualities there that make a friendship possible. Otherwise, you are in conflict with part of your own existence.
He is remarkable in his ability to stay friends with former lovers, and inspiring as well: “I have slept with thousands of women, and they still like me,” he says without a hint of braggadocio. They attest to as much: “Nobody can really let go of him,” one longtime girlfriend declared. “You can hate him, hate him, hate him, but at the same time you have all these emotional mushy feelings about Hef. That’s why he’s still friends with all of us.” Indeed, they are always welcomed back onto his grounds, as they never do leave his heart. And so you see them turn up with their children for the Mansion Easter egg hunts. You see him beam when they tell them about their new lives and new loves. He has never, in fact, actually left a relationship besides the very first one, his early marriage to Millie. Since then, they have all left him, largely because not one of them could make him hers alone. And yet even Millie, who remarried twice and successfully raised his first two children, went to work for decades in his company’s personnel department, never really moved all that far from him. So, too, there is the most literal of aftermath connectives, that of the second Mrs. Hefner, Kimberley, for whom he purchased the estate adjacent to Mansion West, on the other side of a large stone wall into which a gate was set so that she and their two young sons could readily come and go. They would remain close in every meaningful way. “She probably loves me more now than she did when we were married,” he said some years after she had become the Very Special Neighbor Lady, literally the Girl Next Door. This ability to remain connected is an art form all his own.
If It Goes Away, It Will Come Again
The best antidote for a lost love is a new one.
We delude ourselves with the notion that somehow there is only one person out there who is a soulmate waiting for you. Emotionally, you don’t fully believe that you can ever have those feelings again for someone new, that you’ll ever find another comparable. That’s an illusion. You can find it again because what you’re really finding, by and large, is someone with common interests onto whom you can project your own needs and desires.
The reality is that life, especially in this regard, is like a movie: There are many appropriate people who can be cast in that costarring role. When you’re dealing with lost love, it’s time to just start the casting process all over again.
Only Fools Don’t Fall Once More
Broken hearts are like broken legs. They needn’t be fatal. Only a foolish person doesn’t leave the heart open for the joy and pain of love again. If not, you are the loser for it. In fact, you are half alive if you are not either in love or willing to continue to have the capacity for those feelings.
Time Itself Tells the Truth
I see relationships at the time through a romantic haze. Only later on do you get some sense of what the relationship was really all about.
“We’ve all been there,” he has said of love gone awry. “We’ve all had our punches in the gut.” His favorite film is Casablanca, and he often sees himself as Rick Blaine waiting at the Paris train depot for Ilsa Lund, who never comes, reading her farewell letter in the rain, which blurs the ink. He often views himself as the guy left standing in the rain, if only temporarily. One of his secretaries once noted: “He imagined at every party that he would see a girl across a crowded room, their eyes would meet, violins would start to play, and he would feel that pit-a-pat.” So it was that three days after Barbi had moved out for good, he threw himself a party stocked as ever with dozens of beautiful women. And there his eyes met those of a cherubic nineteen-year-old former Bible-school teacher named Sondra Theodore. Violins did not play, but Barry White’s “Baby Blue Panties” did, a
nd they danced to it as their first dance and made love that very night. She would soon be wearing a diamond necklace that spelled out the words Baby Blue and would be known for the next five years as his Special Lady. Moss, it turns out, grows only outside the Playboy Mansion.
Part 2
HEFSTYLE
The Mansion Life
And so one man created two houses and all men would forever want to go to these houses, to be inside. It began with a house in Chicago, where he too began: “I remember, in the days prior to the magazine, walking the streets of Chicago late at night, looking at the lights in the high-rise apartment buildings and very much wanting to be part of the good life I thought the people in those buildings must be leading.” And so he wanted. And so he got. Eventually, that which was once considered urban good life would, in this particular Chicago house, under this particular man’s sway, turn into Good Life supernova. This house, his house, of course, was the original Playboy Mansion, a stately turn-of-the-century monolith, a mere seventy rooms looming, glistening, three blocks from Lake Michigan, imposing its majesty on a leafy Gold Coast street of swells all forever to be outswelled. Six years into his empire-building, in a 1959 year-end letter to stockholders, the manor’s prescient future occupant—this thirty-three-year-old workaholic editor/ publisher/dreamer—wrote, almost as an afterthought: “On the personal side, we’ve bought a house at 1340 North State Parkway, which should make the living considerably easier and more pleasant. It is a magnificent place, with a giant main room that will be great for parties; we’re building an elaborate indoor swimming pool downstairs that will make this mansion the talk of all Chicago. It should help me get away from the office scene a bit and relax a little more.”
Hef's Little Black Book Page 2