1. Don’t get married just because it’s the thing to do.
Hefner married his first wife Millie because, in his own words, “It was simply the thing that you did,” reported Steven Watts in Mr. Playboy: Hugh Hefner and the American Dream.
2. Sleep with your sister-in-law to keep things interesting.
After dabbling in some light swinging, Hefner and Millie attempted to switch partners with his brother Keith. Millie decided not to, but Hefner ended up sleeping with Keith’s wife Rae.
3. You might think you’re not into dudes, but you don’t know until you try!
Hefner once had a gay tryst: “Hefner’s thirst for sexual experience became so strong that he even had a one-time homosexual experience,” Watts writes. “One evening in downtown Chicago he was propositioned and, according to friend Eldon Sellers, he ‘thought, what the hell. Found it an interesting experience. As far as I know, the guy just gave him [oral sex].’ “
4. Stay married for the kids.
Hugh’s longest marriage was to Kimberley Conrad, with whom he had two sons. They separated after nine years together but stayed married until 2010. “I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys,” Hefner said.
5. Proximity to an ex does not necessarily kill your social life.
Kimberly lived in a house next door to the Playboy Mansion for years after she and Hefner separated, while he had numerous other girlfriends.
6. Don’t just drop a former partner like they’re yesterday’s news because they might have stuff you can use.
Hefner and Playboy After Dark star Barbi Benton dated for a number of years, but when they finally broke up because he didn’t want to get married again, they remained friends; he and his “Girls Next Door” went to visit her in Aspen at the house she shares with her husband and she’s stayed at the Mansion.
7. Practice forgiveness when your ex-fiance starts blabbing about how bad you are in bed.
Hefner married his current wife Crystal Harris this past New Year’s Eve, after she cancelled their first wedding just a few days beforehand. He also forgave her for comments she made on The Howard Stern Show, like when she said, “I’m not turned on by Hef, sorry” and explained that they had an almost non-existant sex life.
8. But if someone cheats on you, don’t ever get over it.
Hefner never got over the reported infidelities of both his first two wives.
9. Heartbreak should never ruin a good business relationship.
10. Make sure your employees are hot and then sleep with them.
In his heyday, Hefner has said that he dated as many as 11 out the 12 covergirls for Playboy magazine in a given year.
11. Don’t take getting sued by an ex-lover too seriously.
“Carrie Leigh, 25, the most recent of Hefner’s anointed, has risen from the swaddling bandages of plastic surgery to turn against her mentor,” reported People magazine in 1988 of Leigh’s $5 million case against Hefner. She eventually increased the suit to $35 million “to dissuade (Hefner) from maintaining his long- enjoyed practice of seducing teenaged girls, supporting them for a few years and then discarding them.” Leigh eventually dropped the suit and got married.
12. It’s okay to use a mole to tell your twin girlfriends apart.
Everyone does it.
13. Your girlfriend will like it if you number her.
Even when he was dating seven women, Hefner always had a “Number One” girl.
14. She will also like it if you refer to her as one of “the herd.”
“I thinned the herd a couple of years ago because there were some rivalries, some petty jealousies and I was trying to emphasise the quality,” said Hefner in 2005 when he was dating just Holly, Bridget and Kendra of E!’s The Girl’s Next Door.
15. Film everything.
Not like that! Hefner is a notorious scrapbooker and his love of documenting his life spilled over into the SIX seasons of The Girl’s Next Door, where he aired out his relationships with his three girlfriends in an edited fashion.
16. Treat your girlfriends like your kids.
Hefner reportedly gives his ladies a stipend, but at a price: “Every Friday morning we had to go to Hef’s room…[and] ask for our allowance: a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases,” ex-girlfriend Izabella St. James wrote in her tell-all book about him. “Everyone had to be on the Mansion grounds by 9pm every night — unless we were out with Hef at a club or a function. People honestly did not believe us when we told them we had a curfew at the wild and crazy Playboy Mansion.”
17. Baby oil is the best way to keep things hot in the bedroom.
“There’s baby oil, there’s toys flying every which way, there’s all these girls naked. It was like watching a movie,” Pamela Anderson told Esquire about the time she accidentally walked in on Hefner with some of his women.
18. Most importantly: Having a “type” won’t help you find love.
“Have you always been into blonds?
No, my first wife was a brunette and Barbi Benton, my major romantic relationship of the early 1970s, was a brunette. But since the end of my marriage, all of my girlfriends have been blonds. I have made the comment that Picasso went through his pink period and his blue period before he arrived at his abstract period. I am in my blond period.” (2010)