Hef's Little Black Book

by Hugh M. Hefner

  Hef’s Little Black Book

  Hugh M. Hefner and Bill Zehme

  To Love, lost and found

  Contents

  Part 1 The Chase

  Of Pursuit and Romance

  Part 2 Hefstyle

  The Mansion Life

  Part 3 The Great Indoors

  Hef’s World of Film, Food, and Adult Games

  Part 4 The Business of Life

  Dreams and the World

  Part 5 Inside the Bedroom

  Making Love Like the Master

  Epilogue

  How to Live Long and Influence Playboys

  Acknowledgments

  Copyright

  About the Publisher

  Part 1

  THE CHASE

  Of Pursuit and Romance

  The high school dream girl that got away, Betty Conklin.

  The one he loved first did not love him back.

  They jitterbugged together and laughed together, and his heart leapt whenever he saw her, whenever he thought of her. But she did not love him back. This was the summer before his senior year of high school, and she had asked another boy on a hayride, and he would never be the same because of it. “I turned myself into a different guy,” he would recall. This different guy was self-assured, a dapper fellow whose new wardrobe bespoke his reinvention—the jaunty flannel shirts, the yellow cords, the saddle shoes. He now wrote for the school paper under the byline Hep Hef. He also wrote songs and drew cartoon strips that chronicled the arc of his young life and his young loves. He learned then that he lived largely to be in love, to pine, or to yearn. He learned that his heart felt best when aflutter. Of this time, a classmate buddy of his later remembered: “His interest in girls was intense. Hef was constantly falling in love, one girl at a time, and would be smitten for maybe a month or so. If he wasn’t in love, he felt incomplete and unhappy.”

  This would never change. The boy was father to the man he would become. And the man he would become loved women, one after another ad infinitum, with the wide-eyed exuberance of the boy in saddle shoes. As a man, he would be almost naive in love, giddy and intense—one friend aptly nicknamed him High School Harry, this in his fifth decade—and yet the ad infinitum would also make him aware in love. He would repeatedly declare: “My life has been a quest for a world where the words to the songs are true.” He meant the love songs of yore, the dreamy ones, the ones Sinatra and Billie Holiday sang while caressing the microphone and suggesting bittersweet romance. Such romance had already been the foundation of his empire. Also, he would say, “For me, being in love is the very essence of being alive.” And “I think life is deadly dull when a relationship becomes routine and boring.” And “I admit that I’m still the same romantic pushover I was when I was young.”

  While there would be sexual adventures beyond reckoning and well-nigh-innumerable bedmates, he always pursued primary relationships that filled him with fierce longing (even while openly straying therein; he did, after all, have a reputation of epic proportions to uphold). He had romanticized his first marriage to high school sweetheart Mildred Williams until he realized that the romance had faded, that he was not built for marriage after all: “It was a period of dreams lost, dreams set aside—trying to follow a different road, a road not charted in my own terms.” He created Playboy so as to re-create himself, just as he had done at Steinmetz High School in Chicago. His magazine gave him license to play again, and his long-term playmates in the decades that followed—his Special Ladies, as he would call them—gave him reason to swoon head over slippers. He said in the autumn of 1968, at age forty-two, “I’d rather meet a girl and fall in love, and have her fall in love with me, than earn another hundred million.”

  In fact he had met that girl months earlier on the set of his syndicated television show Playboy After Dark. She was a petite eighteen-year-old coed who resembled the one he had loved first, the one who did not love him back. This girl, however, would love him back, famously so. Her name was Barbara Klein, whom he would rename Barbi Benton in the pages of Playboy. Over the next eight years she would become the extra-special lady that people thought of most whenever they thought of Hef in love. “Barbi became a kind of Hollywood version of the teenage romance I never really had when I was in high school,” he said later. “I was crazy about her.” On the night that they met, he danced with her to the song “This Guy’s in Love with You.” He softly sang the lyrics into her ear and, as ever, believed those lyrics were true.

  When You Know for Sure, You Know for Sure

  I asked Barbi out the first night we met. “But I’ve never been out with anyone over twenty-four,” she said. “That’s okay,” I replied. “Neither have I.”

  Being in Love Feels Far Better Than Not Being in Love

  Everything changes when you’re in love. The food tastes better. The music is sweeter. Everything is a little more delicious because you’re sharing it with somebody you care about.

  If you are a romantic, I think it’s possible to fall in love with somebody across a crowded room. Essentially, love is an illusion. It’s something you project. And it has a great deal to do with what love, or youthful fantasies of love, came before. We tend to repeat ourselves and fall in love with variations on the same person over and over again. If you think about it, you’ll know what I mean.

  “A romantic relationship for me is an escape from the challenges and problems I face in my work,” he once said. “It’s a psychological and emotional island I slip away to.” Rarely has he been cast adrift from any such island for very long, as he indicated in a memo to his attorney in early 1988: “Throughout the 1960s, 1970s and 1980s I have had a series of serious romantic, live-in relationships that included Cynthia Maddox, 1961–1963; Mary Warren, 1963–1967; Barbi Benton, 1969–1976; Sondra Theodore, 1976–1981; Shannon Tweed, 1981–1983; and Carrie Leigh, 1983–January 1988.” The reason for the memo, incidentally, was in response to a misbegotten and quickly dropped $35 million palimony suit filed by Carrie Leigh, the most tempestuous and sexually omnivorous of all the Special Ladies who had inhabited a Playboy Mansion with him. (To wit: “All of these women knew full well that there was little or no possibility that I would ever consider marrying again,” he had added.) The point being, he is lousy at alone and worse than ever when not in love.

  Thus it was in January 1988, two weeks after Miss Leigh had left him under a thundercloud of false accusations (no matter that she had for years been taking other lovers in wide variety), that Cupid drew bow upon him once more. The Playmate of that Very Month of that Very Year happened to be boarding at the Mansion Guest House while working on a pictorial with photographer Helmut Newton. Her name was Kimberley Conrad—a blonde, twenty-four-year-old no-nonsense “Alabama-born, Vancouver-bred angel” (per Hef)—upon whom he had cast his wide High School Harry eyes and all of a sudden sensed renewal attendant. She rebuffed his invitations to a pair of Mansion Movie Nights—French art films, no less—until he approached her once again after the second movie ended, as she lounged on his lavish premises. “I told her that I was really interested in her and would like to spend some time with her,” he would recall. “And she said, ‘Well, I don’t really know you.’ And I said, ‘How are you going to get to know me if we don’t spend some time together?’” (Hef’s line!) “And that line, the simple logic of it—from that moment on, everything changed! We spent that evening together. If this had been a movie, that night there would have been strings and perhaps a little Bobby Hackett horn.”

  Mr. Playboy attempts the Improbable: taking Kimberley Conrad to be his “Playmate for a Lifetime.”

  On July 1 of the following year, she became the second Mrs. Hugh Marston Hefner. Certain lines apparently work better tha
n others.

  It’s Not What You Say in a Pickup Line but What You Don’t Say

  The best line is really not a line. The best line is listening. That is to say: The best way of getting a woman interested in you is to be interested in her. Look for some kind of common connection.

  On the other hand, however, I’ve also had a lot of luck by simply saying “My name is Hugh Hefner,” but that may not work for everyone.

  Try Not to Try Too Hard

  You are never at your best when it really matters, because you are too cautious. Ironically, I think you’re at your best in the beginning of the relationships that don’t matter as much to you, when there isn’t too much at stake. You are at your worst when it really counts.

  Just try to relax and take it one step at a time.

  Say It When You Know It— As Long As You Truly Believe It

  Tell her that you love her as soon as you think it’s true. There’s nothing wrong with wearing your heart on your sleeve.

  The best thing that you can bring to a relationship is what you’re really thinking and feeling. The worst thing in a relationship is deception and game-playing.

  Eagerness in love would always be both his blessing and curse. It had failed him with his fateful high school crush—her name, by the way, was Betty Conklin—although he harbored vestiges of that crush for years to come. (Poetically, five decades after high school, as his marriage to Kimberley Conrad unraveled, it was Betty Conklin that he kissed—platonically, of course—at the stroke of midnight to welcome in January 1, 1998, when she came to his annual Mansion New Year’s Eve bacchanal.) “Betty represented to me the fulfillment of all my boyhood dreams,” he would note. “I projected everything that I was interested in, everything I had observed in my life, all the dreams that I had extracted from movies, all of this onto her. She couldn’t possibly have lived up to that. It was an illusion.”

  The dreams he projected onto Barbi Benton, however, would stick better, if only because he became wise enough to learn some patience. While there was a twenty-four-year age difference stacked against them, patience and a knack for playing games of the heart only emboldened his resolve to capture hers. For instance, she wouldn’t allow him to bring her back to his Sunset Boulevard penthouse alone: “That would’ve been a mistake! I had high morals and didn’t want to be taken advantage of, so I thought that the best way to avoid that was to go out and be among people with him.” He played along, didn’t push too hard, even acceded to her unwillingness to let him pick her up at her UCLA dormitory (in his limousine, natch) for their dates. “I always drove my own car to meet him at restaurants or clubs,” she would say. “But whatever he was doing, he was charming me. He had much more charm than the boys I saw in college. He was wonderful and cute, even though I thought he was too old.”

  Then, too, there was the matter of her virginity, which she had no intention of relinquishing any time soon. Two of his earlier major loves, Cynthia Maddox and Mary Warren, along with scores of other young women, had also presented him with the same challenge, which usually culminated in the same result. Feelings intensified, as they are wont to, and walls changed to portals, as his gentleness would impress each woman he ever knew. Of Barbi, he said, “So I waited months. I didn’t want to scare her away.” She came to Chicago in February 1969 for what would be their first Valentine’s Day together. His secretary had shown him his horoscope for that day; “it said something encouraging about consummating an affair,” he recalled. That night they spun on his Round Rotating Bed in his Master’s Quarters and made love for the first time, as only a romantic would have it. Said Barbi: “It was too late to turn back. It was like, Now is the night.”

  Hefner Versus Freud: It’s Not About a Cigar, Really

  Women want the same things men want. They want to be loved and taken care of—emotionally and in other ways. They want a relationship that permits them to grow.

  Here Is Why You Want Her

  What makes women sexy is partly physical image and partly what they’re thinking—how they manage to express it in both appearance and what they say. A woman who thinks sexy is likely to appear sexy. It has a lot to do with spirit and attitude. That, combined with vulnerability, can be tremendously appealing. A woman you want to both protect and possess is perhaps the sexiest woman of all.

  There Are Rules to the Game, Most Unfortunately

  There’s a danger in the early part of a relationship: If you appear to care too much, sometimes a girl may back away. She may often be more attracted to somebody who she thinks is hard to get—just as a guy often is. Of course there’s nothing rational about that. As a matter of fact, it’s counterproductive. But it’s a reality. Unfortunately, it then becomes a game, which means you have to sometimes hold back true feelings to keep her from running away.

  Too many guys pay too much attention to what they have on their own minds and miss the cues and clues that may establish a common connection. Don’t just think about what you’re feeling; think about what responses you’re getting and are likely to elicit from what you say and do. The key to it all is not simply following your heart, but paying attention and listening.

  Blondes are his weakness: There would, of course, be a blonde preponderance throughout his life—every hue of gold and yellow and flax, from platinum to strawberry to dusky to dirty and all shades in between. In particular, after his separation from the blonde Kimberley Conrad Hefner, he seemed to specialize exclusively in the tint. Blonde posses of three or six or eight would flank him in public and share his vast bed in private. His fascination with blondness—the shimmer and spice and allure of it—began as most of his yearnings had: at the movies, at the Mont-clare Theater on the West Side of Chicago, where a young and impressionable Hugh Hefner saw flickers of a life larger and richer than he could imagine. It was Flash Gordon’s space girl paramour, the radiantly blonde Dale Arden, who stirred him first, in the thirteen-part 1936 serial Space Soldiers: “That was the only really sexy serial ever produced! The final scene was an open-mouth kiss!” This image would never leave his fantasies and he would look for a bit of Dale Arden in every blonde who entered his viewfinder thereafter. The irony, however, is that Dale Arden was played by a nineteen-year-old actress named Jean Rogers, a brunette who dyed her hair blonde for the role. (Not that he wouldn’t have an everlasting weakness for brunettes as well, but still…)

  * * *

  Of Hef and Hair Tint

  WHAT COLOR MEANS

  Per unimpeachable experience, what are the qualities of allure specific to…

  BRUNETTES?

  There is almost a wife-and-mistress connection with brunettes and blondes. A lot of the brunettes with whom I’ve managed to fall in love represented not only respectability and home and marriage, but also something deeper and more romantic.

  BLONDES?

  What you get with blondes is something more dangerous and forbidden. There is a fascinating, universal attraction to them, representing sexuality and danger. So many blondes come out of the bottle, which is a daring choice. It’s flashier and they know it.

  AND WHAT ABOUT REDHEADS?

  Bottle or natural, redheads are a variation of blondes for me—danger.

  * * *

  Understanding Their Sudden Hair Moments Can Be a Minor Art Form

  When they change their hairstyle or hair color and you don’t like it, don’t comment on the way they look now. Just gently suggest how much you liked the way they looked before.

  When She Asks “How Do I Look?”—Tread Carefully

  You start with “You look perfect.” Then if you don’t mean it, you say “Or you might try…”

  Expressions of Affection Never Hurt

  If she lives someplace else, it’s a good idea to let her know that you’re thinking about her with, say, a card, an unexpected phone call, or flowers. I’ve always favored roses. A single long-stemmed rose can make a surprisingly amorous statement.

  His gestures of love would eventually become monumen
tal in sweep, but they began innocently enough. Summer 1944: Before shipping off for army infantry training (he would serve stateside for two years), he had pursued a romance with the girl he would marry five years later, sweet and pretty Mildred—Millie, really—Williams, a classmate he noticed only as his bright senior year at Steinmetz High waned. That summer they smooched (nothing more, not in this chaste era), and then he was gone and wearing fatigues and living in barracks, where he could devote himself—devote his heart—to pining for his girl back home. He wrote her bundles of letters—guileless and beseeching at once—from army bases here and there. As sex was still a distant reality (his own virginity remained intact until he was twenty-two, so as to conquer Millie) while it was also becoming foremost in his mind, this son of two repressed Midwestern Methodists rhapsodized thusly in one such missive: “HOW I’D LIKE TO TAKE YOU IN MY ARMS and hold you so very close to me, and kiss you, and more, a heck of a lot more! But maybe I’d best skip over this lightly or I’ll have you blushin’ again. Needless to say, I think about being intimate with you. Think about it a lot, right or wrong.” Eventually he would know he was right to think about it, and he would tell generations to come just how right he was. Still, it all begins with the smallest gestures.

  You Need to Know That You Are Who You Are

  How much a man can change for a woman depends only on the man. I think the real question is, How much should you change for a woman?

  One of the great dangers in relationships is that a woman falls in love with you and you with her, and then she tries to change you. The truth is, if you haven’t changed who you are by the time you are in your twenties, you aren’t going to be doing much changing thereafter.