Hugh Hefner explains why he dates women young enough to be his granddaughters

The NY Times has an extensive profile and interview with Hugh Hefner, the 84 year-old Playboy found who is currently engaged to a 24 year-old Playmate. They paint a picture of Hef as a kind of durable icon of years gone by, a living symbol of a sophisticated outlook on sex that has become almost quaint. Despite the way that Hef continues to take up with women who are young enough to be his granddaughters, he’s portrayed as a decent guy who is not trying to hide his lifestyle or his preferences. I get a similar impression of him, but that doesn’t mean his actions are any less skeevy. Here are some choice excerpts:


On how Hefner isn’t a sleeze
Hefner is a little odd, certainly, but not a sleazebag. He has none of Bob Guccione’s oiliness, or Larry Flynt’s leering vulgarity. His manner is open and direct, and his language is as clean as a Midwestern Rotarian’s. By his own lights, having purged himself of the shame and hypocrisy that is part of most Americans’ sexual baggage, he leads a life that is exceptionally honest and moral. It’s also a life that is exceptionally well documented.

Hef’s sexual history and how he founded Playboy
A late bloomer sexually, Hefner didn’t masturbate until he was 18, and after years of foreplay, he finally managed to lose his virginity when he was 22, but he read Kinsey as if Kinsey were a prophet and became a student of marriage manuals and sex handbooks. Playboy was the sort of sophisticated, sexually adventurous publication he fantasized about. He scrounged money, including $1,000 from his mother, and laid the first issue out on the kitchen table, writing much of the copy himself. His greatest piece of luck was his choice of the first centerfold: a nude calendar photo of Marilyn Monroe taken four years before. It remains by far the sexiest of all Hefner’s pinups. Where subsequent Playmates all have a health-club aura, as if they’ve lately come from the tanning bed or a Pilates session, Monroe, flushed and languorous, looked as if she just had an orgasm.

On how Kimberley Conrad cheated on him
Hefner now says that his 1989 marriage to Kimberley Conrad, January Playmate of the Month the year before, was an attempt to seek refuge — a “safe harbor from the waves.” “I was not well, and I felt my years,” he told me. “I felt much older then than I do today.” He and Conrad broke up in 1998, though they did not divorce until 12 years later. “During the marriage I was faithful,” he said to me emphatically, “and she was not.” (Hefner, for all his advanced views, clings to the double standard and has never entirely got over his first wife’s admission that while they were engaged she had an affair with a high-school coach.) The aftermath, he now admits, was “overcompensation,” as he began dating posses of women, including one named Brandy and a pair of twins named Sandy and Mandy. “You can’t make this stuff up,” he said, laughing at himself. At one point, early in his ’80s, he was living with seven young women and trying vainly to enforce a 9 o’clock curfew to keep them from dating anyone else.

On how Hef keeps scoring women
What do the women see in him? A friend, a mentor and a meal ticket more than a sex symbol, most likely. Live-in status at the mansion brings with it — or used to bring, before Hefner pledged himself to Harris — a stipend of $1,000 a week, paid out in cash by Hefner every Friday, and there was also free hair care, a car allowance and additional sums available for breast and dental implants and for special-occasion clothing. Sex with Hefner was not a requirement, strictly speaking, though most of his girlfriends did sleep with him, it appears, either out of gratitude or because of pressure from the others.

Crystal on their relationship
When I asked Crystal Harris whether her relationship with Hefner was sexual, she looked at me for a moment. “I don’t know how to respond to that,” she said, and then added, after a pause: “You mean sexual relations? Sure.” But she went on: “Hef has hooked up with a lot of people, but that’s not what makes him happy these days. He’s much happier just cuddling and snuggling with the dog.” They watch a lot of old movies together, she said, and she also likes trying to break him out of his unbudging routine. Just recently she persuaded him to try sushi and shepherd’s pie.

Hef on why his girlfriends never age
“Well, I guess I know what I like,” Hefner said when I asked him if he didn’t think it odd that as he got older and older, his girlfriends remained the same age, all in their 20s and all conforming to an unoriginal model of perky blond buxomness. He was in his standard daywear — red silk smoking jacket and black silk pajamas — and sipping a Pepsi while sitting in the mansion’s largely bookless library underneath a huge breast-baring ceramic bust of Barbi Benton, one of the few brunettes ever to catch his eye. “You do give up something in the process,” Hefner went on, acknowledging that most of his girls have never listened to his kind of music — jazz and the big bands of the ’30s and ’40s — and have never heard of Betty Grable and Alice Faye (who probably imprinted that sexy blond template on him in the first place). “But you gain something, too. There is something wonderful in the student-teacher relationship — the rediscovery, the chance to have a relationship with a younger woman. It permits you to see the things you love with a fresh eye, makes them exciting again. And I don’t think there’s any question that surrounding yourself with youth keeps you younger.”

Hef is just an old dude after all
“It will be easier to perpetuate my story when I’m not around,” Hefner told me. “Because then nobody will be pissed off that I’m still getting laid.” He also pointed out that his mother lived to be 101. Then he went back upstairs to his legendary bedroom, which these days is a bit of a mess: stacks of old movies on tape and DVD, knickknacks and tchotchkes everywhere, childhood photographs on the mantel, panties dangling from a chandelier and, nestled together on a sofa, a couple of hundred stuffed animals. It looks less like a love nest than the cave of a hoarder unable to let go.

[From The NY Times via Huffington Post]

The article also talked about the future of Playboy, which is expected to be taken over by Hef’s sons from Kimberlyy Conrad, now young adults at age 19 and 20. The journalist admitted he only spoke to the boys briefly but calls them “sweet and slightly spacey,” adding that they “seem a little young for their age.” They must take after their dad that way.



Photo credit: WENN and Fame

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46 Responses to “Hugh Hefner explains why he dates women young enough to be his granddaughters”

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  1. Jayna says:

    They’re inhouse prostitutes, basically. But Hef is honest. Live here, have sex with me on occasion, free perks and allowance and follow my rules: nine a.m. curfew, can’t travel and stay somewhere overnight without him, on and on. Paid prostitutes or paid mistresses.

  2. Rita says:

    “a kind of durable icon of years gone by, a living symbol of a sophisticated outlook on sex that has become almost quaint.”

    Like smoking but more “quaint”.

  3. poppy says:

    because he’s yucky and prejudiced, the chicks are skanky ignoramuses, and he is rich.

  4. Kaboom says:

    At $1000 a week they’d be very poorly paid prostitutes, especially considering what they could make on the free market.

  5. GIrlyGIrl says:

    NYT-So Mr Hefner, why do you date girls young enough to be your grand-daughters?

    Hef-Cause I’m a disgusting old pervert.

    NYT-Ok thanks Mr Hefner, we’ve got enough here.

  6. Sakyiwaa says:

    this is just interesting. i don’t know why people do the things they do… usually i don’t care as long as no one’s getting hurt. but i have wondered why Hef does what he does. at the end of the day though, i don’t think i’ll ever know the real reason or ever approve of his worldview no matter how many enlightening interviews he gives. in any case, the real truth is; it shouldn’t be my business to care… which is why human behavior is such a piece of work. Hef is a piece of work. but then again, so am i…(rolls eyes)

  7. wonderwoman21 says:

    Ugh I can’t imagine ridding my self of dignity and independence for a paltry $1000 a week. That isn’t crap, that’s barely about four times what you’d make working full time on minimum wage, which isn’t enough to make me sleep with a wrinkly 84 year old man who resemles Freddy Krueger.

  8. QUEST says:

    Hef is going for the world record on the amount of viagra one man can take.

    As for the ladies – well let’s say they can earn much more on the streets.

  9. LindaR says:

    Reading between the lines, there is so much more than what he is saying outright. It’s much easier to be in a relationship in which you feel superior. He dates women that are the age of his boys and yet thinks that they are a bit immature. Really? Maybe he just thinks that’s not the way males that age behave, just females. Didn’t masturbate until he was 18? He is a nerd that has been making up for lost time ever since. He has all the characteristics of a narcissistic Peter Pan and I don’t think I could stand to be in the same room with him.

  10. LindyLou says:

    Why does Hef date women young enough to be his granddaughters?? Because he CAN. (Just like any other rich old perv out there).

  11. DoMaJoReMc says:

    Doesn’t he mean “GREAT, GREAT Grand Daughter”?

  12. beth says:

    just goes to show, inside you never age. :)

  13. mln76 says:

    Whenever I see Hef in interviews or have seen clips of that reality show he comes across as likable. He is a perv and it’s gross to think of him marrying a 24 year old but I don’t think anyone is being abused in this situation everyone has their eyes open and I am just doing my best to pretend it’s not happening.

  14. lilred says:

    Seriously, where else could these girls get 1000 dollars a week free and clear they don’t pay for anything else…lodging provided,food provided, hair care provided, vehicle provided etc. not my cup of tea but I can see where it would have appeal for some.

  15. JustBe says:

    Sure, sure he’s 84 and surrounds himself with newly legal (just over 18), naive young women who he pays to have unprotected group sex with him and to not have a life outside of the mansion (no college, no outside friends), but since he’s not forcing anyone to do anything, you can’t call him a pervert.

    You should, however, skirt or outright ignore any questions on why an 84 y.o. man would want to surround himself with needy, self-conscious, no self-esteem, perpetually post-operative ‘women’. because that they don’t hope/expect/ask for too much from a man, because they don’t talk too much? Because they only ever hope to live in the mansion for as long as he’ll have them and keep getting paid?

    No, no, he’s not a pervert, he’s just someone who’s not interested in having an adult relationship with compromises, trade-offs, mutual respect and sincere love. As long as he’s got some viagra and a fat wallet, he’s got all the love he’ll ever need. Nothing to see here folks!

  16. RHONYC says:

    his sons taking over the business might really reinvigorate playboy, seriously.

    they’ll maybe bring that whole fresh new ‘twit generation’ experience to the whole thing.

    might be interesting…we’ll see.

    i’d hate to see the magazine disappear.
    it’s an american institution. ;-)

  17. Bubba says:

    I’ve always found him a controlling creep. Thanks NYT for validating that impression.

  18. StraightfromA says:

    H.H. is really showing his age. I think he has a stain ! on his jacket in the first pic and the clothes hes wearing haven’t changed since 1998. Especially jarring since he has spent most of his life as Mr. immaculate GQ lifestyle guy. Kind of sad.

  19. DogBoy says:

    skeevy. money can buy anything.

  20. MrsOdie2 says:

    “There is something wonderful in the student-teacher relationship — the rediscovery, the chance to have a relationship with a younger woman. It permits you to see the things you love with a fresh eye, makes them exciting again. And I don’t think there’s any question that surrounding yourself with youth keeps you younger.”

    This is why you have GRANDCHILDREN. And if you love the “student-teacher” relationship so much, be a teacher, you scumbag.

  21. Jo 'Mama' Besser says:

    I donate one (side) hug to the phrase ‘largely bookless library’.

  22. the original bellaluna says:

    Because he has pedophiliac-tendencies. Nuff said.

  23. Isabel says:

    I just keep thinking of the reported endless piles of dog waste in his bedroom. Used thongs and dog shit…that’s sexy.

  24. The Bobster says:

    I thought his daughter ran the business.

  25. latam says:

    This is all very sad, id say he was insecure. Its a bit shit going through life not having found someone you loved enough to have wanted to commit to and grow old with

  26. Kiska says:

    @ Lindylou You took the words right out of my mouth. Exactly. Because he can. Personally, I think he is utterly disgusting.

  27. snarky_pup says:

    Why does an old man date a younger woman? Because he can pretend to be young again while he is with her. Must be a b!tch when he accidentally catches a glimpse of himself in the mirror and has to acknowledge the fact that he is, in fact, an old man though! This whole thing is gross. Having sex with that dirty old bird would severely traumatize me.

  28. Boey Jellodonna says:

    They’re not “basically” prostitutes…they ARE prostitutes. They’re paid to pretend Hef is still virile and sexy because he has no dignity and no self-identity other than being the Hef of old. The girls are playing “death lotto” in the hope that they’ll be the one that’s Hef’s #1 girl when he croaks. It’s a pathetic spectacle.

  29. Kim says:

    He ikes them young because they are young and naive & looking for fame & a meal ticket. No woman his age with half a brain would touch him with a 10 foot pole-they dont NEED him like younger girls do.

    It does make me laugh that he realizes these young girls arent physically attracted to him and want to date men they are attracted to so he enforces a 9 pm curfew!

    He is pretty sleazy any way you slice it.

  30. Sassy says:

    Daughter, Christie, who runs the PB empire, is 59. He is doing succession planning by naming the boys. Good move.

  31. Roma says:

    How many girls are a side piece for married men? A lot that I know of. They get their rent paid, car leased, spending money and vacations.

    You might think that these girls are behaving like prostitutes but I hate to say that many women live their lives like this. I think people stick with Heff more for the fame because yes, you could be making more as a mistress.

    And… wasn’t the $1000 a week said by someone who was with Heff in the 70s or 80s? I think with inflation the most recent girls were getting a little more.

  32. MrsOdie2 says:

    Also, he doesn’t want an equitable relationship. It needs to be all about HIM. Surely he doesn’t learn anything FROM these girls. Except maybe how the young people are waxing these days.

  33. Faye says:

    Just to put this out there…I’m in the same age demographic as his fiancee, and I would not sleep with him.

    Probably didn’t need saying, but I wanted to say it anyway.

  34. crazydaisy says:

    Death Lotto, lol. Sad, strange and probably true.

    HH is fascinating and creepy. Sure he is attracted to beautiful young women – who isn’t? He sees them basically as cuddle toys and he pays to play with them.

    Many 45+ guys can’t stop being attracted to 20-somethings and, unfortunately, trying to hook with them. Very sad, especially cause without deep pockets or fame, the older these “men” get, the less the young girls are interested, if not straight up creeped out.

    Hef, at 80+, is a glorious icon for these sorry dudes. Him and online porn stoke the fires of the pathetic aging male who never learned to be real.

  35. Shay says:

    Old insecure man who can’t accept his eventual demise.

  36. LittleDeadGirl says:

    I have to agree with LindaR.

    I think in a way the man suffers from a sever fear of women. I think he objectivies them because it’s easy that way for him to deal with them and dates only these young, very naive, and obviously not very bright women because he can feel superior. I also think part of it is that it helps him live in this mythical idealized version of himself “The Hef” and feel a sense of immortality. He’s no longer just a man but a symbol. I think once upon a time it was just sex with young hot girls but by now … at his age … I mean how interested in sex can you be at 84 … enough to deal with that vapid ignorance? I just don’t get it …

  37. Narsa says:

    This is what Charlie sheen wants to do , bahahahahaaa !!!

  38. David says:

    That used to make me laugh a few years back on that TV show ‘Girls of The Playboy Mansion, when you’d see that little lighted icon in the background.. ‘I love Hef.’ Probably put there by the man himself. And at the end of the day it all goes to prove just one thing: The richer you are, the more handsome you become. Ha Ha.

  39. what? says:

    “Hugh Hefner explains why he dates women young enough to be his granddaughters”

    because hes a dirty old perv. there, now you dont need to read that bullshit article.

  40. Lise67 says:

    It’s amusing that Hef likes to present himself as some libertine pioneer of the Sexual Revolution,when in fact he’s merely championing the objectification of women & the re-establishment of the harem which is older than sin.As for him reading Kinsey,after reading a detailed account from a former bunny who bailed to married a younger,less flush man,I doubt it.It’s clear that Hefner is no great lover & knows NOTHING about a pleasuring a woman or female sexuality.Not to be indelicate,but basically his sex life involved all the ‘playmates’ taking a prescribed role from stimulation to orgasm.Once the others had er-’prepared’ him-whoever was the current favorite concluded the business in quickie,awkward fashion.Not at ANY time was there any attempt at provide sexual pleasure for the women.Once HE was done,that was it.None of the girls had lives of their own,but spent their days pandering to his wishes or catfighting for #1 position.He went to bed at 9-so did they.He wanted them blond & busty-he paid for them all to have breast augmentation.Hefner is not a champion of equal,guiltless pleasure between consenting adults.Rather he is a narcissist who is still stuck in that masturbatory,objectifying mindset towards women & sex that most men outgrow by the time they’re 16.If he didn’t have money,none of these ‘employees’ would look at him.Get out the popcorn when he dies & watch as all these girls suddenly claim they were his common-law wife entitled to most of the estate.The only love in that house is for Hugh’s money & Hugh’s great love affair with himself.Pathetic,really.

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  42. EvolveIsLove says:

    The most telling thing here has nothing to do with Hef, but rather the assessments by strangers. No matter how philosophically, morally or ethically sound a person’s judgment of his behavior may appear — a human being is free to privately create their experience. Everyone learns from an individualistic approach. Barring physical violence towards another, this is life’s freedom at its finest.
    That freedom of course also applies to the experience of judging another. Ain’t that sweet ?? :)

  43. Tony says:

    Bunch of haters on here. Hef is just living a life 99% of the male population would kill for. This guy is awesome. Sorry ladies, but if every guy had the chance to do what Hef has done and is still doing, damn near 100% of us would jump at it. This includes your boyfriends and husbands who probably fantasize about other women all the time while you think you’re the only one. Who’s the pathetic one here?

  44. sheila says:

    I worked in a nursing home once and he looks like all the “old” men there. He is disgusting looking. And the women?? I would hardly call them Ladies.