Marrying Hef

What’s it like being Mrs. Hugh Hefner?

Hugh Hefner and Crystal Harris

In recent days, amid the coverage of his engagement to 24-year-old Playmate Crystal Harris, Hugh Hefner has taken to disputing accusations that his beloved Playboy mansion is studded with dog doo.

“We only have on[e] dog at the Mansion (Charlie) and he’s house broken,” he tweeted recently.

The British tabloid the Daily Mail had run a piece describing the Mansion as a “squalid prison” run by a controlling senior citizen who, amid decaying surroundings, doled out weekly allowances to his girlfriends and kept sex parties tightly scheduled. The story borrowed heavily from a four-year-old tell-all written by a disgruntled former girlfriend named Izabella St. James, who appears to have a flair for bombast. Still, it’s enough to make one wonder: What must it be like to be married to Hugh Hefner?

Biographies, profiles, and interviews suggest the answer is: probably pretty boring. The Playboy mansion comes across not so much a prison as a singularly unsexy place of strict routines, tight curfews, and old movies. The visionary who popularized the idea of life as a nonstop stag party is, it turns out, a homebody with staid habits and old-school tastes. None of this should really be surprising. After all, Hugh Hefner is 84.

A little marital history. Hefner has been married twice before—in 1949 to high-school classmate Millie Williams, with whom he had two children, and in 1989 to Playmate Kimberley Conrad, with whom he had two more. His marriage to Williams lasted 10 years, and according to University of Missouri historian Steven Watts was undone by a basic incompatibility as well as by Hef’s open dalliances with other women. But his marriage to Conrad, from whom he separated more than a decade ago but only recently divorced, appears to have ended in part because of the playboy’s surprisingly narrow lifestyle.

“Her husband’s rigid schedule seems to have been one source of unhappiness,” Watts writes in his biography of Hefner, Mr. Playboy. According to Watts, every week in the mansion followed the same plan: Four nights, guests came over and watched movies (Monday’s viewing was for men only; Hef dubbed it “Manly Night”); while on Wednesdays, friends gathered to play cards. Watts writes that Conrad resented their highly scheduled existence. She wanted spontaneity—maybe a “quiet dinner together” or a visit to a “piano bar—and time away from the prying eyes of guests.

In a 1999 interview with the Washington Post, Conrad called Hefner “very controlling” and “extremely possessive.”

“He would expect you to be at home, say, at 5:30 or 6,” she said. “Every single night. It was basically on his program. It was a little bit monotonous. Or, if I wanted to go to sleep at 11, he’d want me to stay up with him till 1 or 2 and watch things. I’d say I want to go to bed and get up at 6:30 and work out. He wouldn’t be happy about it. He doesn’t like to be alone.”

After the two separated in 1998, Conrad and their boys moved into a house next door to the mansion. Several years later, here was Hef’s revised schedule, according to another Post story: Tuesday nights, family time with Conrad and the boys. Thursdays and Saturdays, clubbing with his bevy of seven girlfriends. (Over the years, Hef’s stable of live-in lovers has waxed and waned, with seven apparently being about what he can handle. At times it is has been smaller, as when Hef dated a tight-knit trio consisting of a Brande and twins named Mandy and Sandy.)

Hefner has worked hard to portray his lifestyle as one of perpetual play, in which he figures as a sort of benevolent daddy to a happy troop of never-aging, nearly interchangeable, constantly cavorting girls. “I’m the leader of a Girl Scout camp,” he once said. A sign on the mansion’s driveway forever promises “Playmates at Play.”

But this carefree image is at odds with the essential character of a workaholic obsessive who sets exacting terms for how he and his paramours should have their fun. Like Conrad, at least some of Hefner’s live-in girlfriends have chafed under his rules, resenting what one called a “strict” mansion lifestyle in which staffers would log the girlfriends’ comings and goings. They disliked his 9 p.m. curfew. (Necessary, Hef told the Daily Beast earlier this week, “so they wouldn’t be running around on me!”) He has previously admitted to keeping elaborate logs of his sexual activity, calling them “observational notes.”

With the caveat that it’s tough to know the inner workings of any relationship (let alone a four-way one), there doesn’t seem to be any one reason why Hef’s relationships end. Some recent girlfriends have moved on to other men and different careers (reality shows, topless burlesque). According to Hefner, one girlfriend, Holly Madison, wanted to marry him and was crushed when he declined. Several others, after leaving the mansion, have expressed ambivalence about its chapter in their lives. Kendra Wilkinson, who starred as one of Hef’s girls on Girls Next Door, told US Weekly that she saw Hefner infrequently when she lived with him and added that they never went on “solo dates.” She said she was now “totally against” group dating, and spoke of Hefner with a kind of mixed gratitude.

“Hef was kind of like my best friend, but a sugar daddy at the same time,” she said.

So why, given all of this, would anyone want to marry Hugh Hefner? The revolving door of girlfriends points to one possible motive for becoming Hef’s wife: security. Being Mrs. Hefner is a significant step up from No. 1, a position Hef usually confers on one girlfriend when he’s dating a pack. This title is determined, Hef has said by “seniority” and common interests. He used to say—more than a little implausibly—that he and former No. 1 Madison, a onetime Hooters girl, were brought together by their shared love of Bix Beiderbecke’s 1920s jazz work. But being No. 1 is inherently precarious, as Madison discovered. After their breakup, Hefner noted in an interview that “there are girls lined up outside the front gate.”

Marriage to Hef also brings the promise of monogamy. Mr. Playboy author Watts explains that he has long held his girlfriends to a sexual double standard. They are expected to be faithful to him, while he gets to do whatever he likes. But apparently he sees matrimony differently than he did during his first marriage. Hefner claims to have been faithful to Conrad before their separation, and he told the Daily Beast he plans to be faithful in this, his third marriage. Already, Harris appears to have taken on a central role—his most recent other girlfriends, twins Kristina and Karissa, moved out of the mansion almost a year ago.

And whether or not a prenup is in the cards, being married to Hefner probably brings with it some measure of financial benefit: The new Mrs. Hefner presumably won’t have to endure what several former girlfriends have described as the humiliating practice of lining up for a weekly “clothing allowance” of $1,000.

Of course, there is one final reason one might want become Mrs. Hefner: Simple, predictable love, or whatever you want to call it. Hef and Harris seem to genuinely dote on one another. For Christmas, she gave him a portrait she commissioned of the two of them and their dog, the aforementioned Charlie. He gave her an engagement ring inside a Little Mermaid-themed music box. (It’s her favorite movie. We are not the first to note that she was 3 when it came out.)

In interviews, Harris says she doesn’t even notice the age difference. For his part, Hefner praises her devotion, saying they’re “soulmates” and comparing their love to Humphrey Bogart and Lauren Bacall’s. On Twitter, he has gushed: “These are the days, my friend. I hope they never end.”

Clarification, Jan. 7, 2010: Because of a copy editing error, the article originally omitted two sentences from the third paragraph.

Like  DoubleX on Facebook. Follow us on Twitter.