The Freddy Krueger thing was the first image to pop into my mind when I saw that photo too. I think it’s the fedora and the creepy hands. But it’s uncanny, and I’m glad I’m not the only one.
Yeah…I’m 12. 
Hef is certainly not the embodiment of my ideals, but if the best we can muster is “Ew! Old man!” maybe we got nuthin?
Were it an 84-year old woman and a 24-year old man, I’d have the same reaction.
Ick.
Well I can’t honestly say I’d have dated an 84 year old girl when I was in y 20s either, but then I also don’t eat sheep eyes, I don’t do buttsex and I really don’t care for Westerns. Outwardly it’s just a matter of aesthetics.
Maybe Hef picked her because she doesn’t?
Oh, I think the joke is on Hef and has been ever since he started having relationships with women his daughter’s age. Once a taste for young women gets you into intergenerational relationships, you’ve kinda turned a corner.
I’m not sure May-December is big enough to define this relationship. I’m voting for Julian-Gregorian.
Hef’s daughter Christie has largely been credited with saving Playboy. She took over as President of Playboy Enterprises in 1982. They developed the Playboy Channel and the successful videos that bring in a lot of cash. They also cut back on some of Hef’s extravagant spending. Otherwise the magazine would have gone under back in the 80’s.
Christie retired in 2009. She’s 58. Hef’s oldest son is a couple years younger. There’s not much about him on wikipedia. Then, Hef had a new family in the late 1980’s with Kimberly. Those two sons are almost 20. I imagine at least one of them will work for Playboy after college.
I’ve noticed my interest in women has changed in the last ten years. I tend to notice attractive women in their mid 30’s. I can’t imagine dating a 20 year old.
This isn’t a big deal. You know there’s a huge prenup and the girl is probably stupid enough not to know a decent lawyer to read it beforehand. Secondly, he has a 50 something year old daughter from his first marriage who runs the business. You better believe she’s not a pile of stupid shit; she’s the one who took them online and keeps them solvent to this day.
It’s the same deal with Joe Hardy, the 84 Lumber tycoon. He has a 50 year old daughter from his first marriage who runs the business; he’s given a small sum to live on and women still flock to him because they are stupid and naive and think he’s the rich one. His daughter legally has all the rights and is the CEO or COO. Every girl has a prenup that he’s married but his first wife.
If these girls were smart, they’d go to well off bars and find medium-sized small business owners, wealthy doctors (dematologists or radiologists, not family docs) etc. They’re the ones who are well off and work hard enough to have little contact with women, so they may actually think the women like them for who they are, and in turn not require a prenup.
Or maybe she loves Hef and doesn’t care about the money?
Cite?
And to think it used to be that the people* requiring *the prenup were the ones presumed to have a jaded view of humanity… 
Y’know, I’m wondering if “trophy wives” should really form an association and get themselves some good Public Relations firms working for them, they seem to badly need it …
As Patton Oswalt twittered: "Hope when I turn 60 I can think, quietly, “My wife is being born somewhere.”
From what I understand, Hef is trying to take the company private again. Presumably he does actually have a large personal pile of money to do so.
I interviewed at Playboy several years back. Every single person I talked to, indeed every person I saw, at Playboy was female. Apparently they have a very difficult time hiring men due to jealous girlfriends and wives.
Yes, but you haven’t spent your entire adult life evaluating beautiful young women - professionally. I do know that Playboy featured a lot more women in their 40s (like Vicky Lamotta) as Hef and his readers aged. I let my subscription lapse as the magazine changed in the 00s as they tried to reach the “Lad Mag” market, so presumably is with younger girls because that is what the readers they are trying to attract are attracted to. Or maybe he’s just too old and too rich to give a shit what anyone else thinks.
Possibly they have more desire to get famous than rich? I checked the Hefner Wikipedia page and started clicking on links to pages about his previous paramours. Every single one of them is now a model, actress, sportscaster…something in entertainment. Not one of Hef’s girlfriends decided to go teach high school or run a non-entertainment business. They wanted fame, and sleeping with an old man was a reasonable path to that fame from their point of view. Even cheesy fame like feature dancing in a strip club is worth it if their goal is to make a lot of money with very little actual labor.
BAHHAHAHAHHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA!!!
<sob><sob><pant><pant>
BAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHHA
<wipes tear from eye>
No really - yes I’m sure true love could be a possibility.
Some info on the next Ms Hefner.
http://www.people.com/people/article/0,,20453326,00.html?xid=rss-topheadlines
Sounds like she had a pretty full life before getting engaged. I wonder if Hef will be happy with her off touring with a band?
You are missing a major, major point here. A prenup means that what you get on a divorce is predetermined. It doesn’t mean you get nothing. Unless you know what this girl gets if she and Hef divorce (or he dies) you have no idea how this equation works. I think you might well find that getting a divorce settlement from a medium-sized small business owner etc would amount to a hellava lot less than the (relatively) tiny small proportion of Hef’s wealth that this girl might get based on her prenup.
Obviously she’ll be getting more than a doctor making say, a mil a year. But I’m talking about numbers here: how many women before her wanted to marry him and failed and were dismissed, no money in hand? If fame’s what your after, fine. But I’m talking cash. How many other Playgirls slept with him (rumored that you had to sleep with him to get on the cover itself) only to not be offered a ring? 12 girls a year for 40 years, so something like 500 women (and these are the cover girls, not the ones within!) could have spend their youth going after a more solid investment.
If you’re running the numbers, you’re far better off with someone making 500k-2 mil a year and receiving alimony for years down the road. I’ve seen many specialists (orthopedic surgeons, opthamologists, radiologists) swindled by their first wives. They get a hefty sum in the form of future earnings. I’m saying that you’d be best off preying upon those who are not lawyered-up, and anyone making more than a couple million per year has an attorney at the ready.
Sure, that would make sense in, say, Norway, where everyone is calm and rational. But this is AMERICA. where we’re all encouraged to leap for the brass ring, or the gold dick as it were. Millionaires settle for smokin’ wives and trade them in every few years. Billionaires rent them on spec and try out new ones every few weeks.
I’d guess the losers in the Hef lottery get picked up on waivers by the mere millionaires who hang out around the grotto at Hef’s parties.
It was a book that came out a few years ago. I read the salacious excerpts online. I believe it was the one written about here: Hugh Hefner Has Sex Twice A Week, Playmates Describe Orgies | HuffPost Entertainment
