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Playboy's Hugh Hefner engaged to 24-year-old former playmate
December 26th, 2010
08:48 AM ET

Playboy's Hugh Hefner engaged to 24-year-old former playmate

Who says May-Miss December romances don't work?

Hugh Hefner, the 84-year-old Viagra-popping founder of Playboy, is tying the knot for the third time.

This time the lucky gal is 24-year-old Crystal Harris, December 2009 playmate of the month.

“When I gave Crystal the ring, she burst into tears,” Hefner posted on his Twitter account. "This is the happiest Christmas weekend in memory."

“Yes, the ring I gave Crystal is an engagement ring," he clarified later for those asking if it was merely a Christmas present or a step forward for the couple.

Hefner posted that he and Harris spent the night before Christmas watching a movie, then exchanging gifts. Hefner had a few for his girlfriend, which Harris tweeted pictures of, including the legendary diamond Playboy watch.

His big gift was the engagement ring. It was a "memorable Christmas Eve together," Hefner tweeted.

Video: The world's ultimate playboy gets engaged

Hefner's love life has, of course, been well documented including the popular reality show showcasing a trio of girlfriends in "The Girls Next Door."

Hefner and his previous wife, 1988 playmate of the year Kimberley Conrad, were married in 1989 and separated in 1998. They divorced this year. Now Hefner will walk down the aisle half a century after his first marriage in 1959 to Mildred Williams.

But if you think Hef might not be the exact icon of monogamy or a perfect relationship, he begs to differ. In an interview with RadarOnline.com after the breakup of Sandra Bullock and Jesse James, he said more than anyone, he knows all of the sides to a relationship and what makes one work.

"I was married and completely faithful for eight years," he told Radar. "I lived a single life, a playboy lifestyle, before and after it, but while I was married I was faithful to it."  Hefner told the New York Times magazine in July that he uses Viagra which he called "God's little helper" a couple of times a week.

soundoff (1,631 Responses)
  1. BSEA

    SURE so the girl likes 80 year olds....HEFF its over just step off ....this is beyond stupid

    December 27, 2010 at 1:02 pm | Report abuse | Reply
  2. Timmerson_04

    Money really does buy happiness!

    December 27, 2010 at 1:06 pm | Report abuse | Reply
  3. Melinda

    I make a good living. Never, would I put up with some ditzy twenty year old boy. I wouldn't want anything to do with a stud that wanted me just so I could keep him in the lifestyle which he thinks he deserves because he's a pretty young thing.

    December 27, 2010 at 1:07 pm | Report abuse | Reply
  4. Zeke

    The men who post here are just envious of Hef because he has a beautiful girl at his age. Of course she's with him for the money and publicity and because he has not got much longer to live; but get over it. He can do it because he CAN. More power to Hef and all the men who can do it. On the other han, the women who post here are envious because they have not found somebody like Hef to buy all the materialistic crap they want to buy and because she is prettier than they are. Enough said!

    December 27, 2010 at 1:08 pm | Report abuse | Reply
  5. badtothebone

    If it was the other way around, she would be called a child abuser darn double standards it is still very much "A man's world"!

    December 27, 2010 at 1:17 pm | Report abuse | Reply
  6. Brasil1958

    It basically says if you have fame and fortune you can have any dame you want and vis versa.

    December 27, 2010 at 1:20 pm | Report abuse | Reply
  7. bookenz

    What a gross old man.

    December 27, 2010 at 1:22 pm | Report abuse | Reply
  8. Ultimate Cynic

    All women are gold diggers. Some just have better looking shovels.

    December 27, 2010 at 1:23 pm | Report abuse | Reply
    • Bear_Down

      Diggin that gold and those panties – got to love it!!

      December 27, 2010 at 1:39 pm | Report abuse |
    • Isayyy

      Why does he want to get married? He could get as many pretty girls as possible without marriage. He had so many girls at the sametime, same bed. Maybe this time is for REAL. Something about this girl really got him.

      December 27, 2010 at 1:41 pm | Report abuse |
    • Janet

      I realize you are a cynical SOB but not all women look at the size of a mans wallet or his instrument for that matter. I have dated my share of not the best looking guys, guys with small packages, and yes broke guys! I am 36 years old and married to one of those that most people wonder why I took a second look. He doesn't make a lot of money & he won't win a prize for his looks, but he makes me laugh and he treats me good. What else is there?

      December 27, 2010 at 1:49 pm | Report abuse |
    • JonPeter

      She probably a practical and reasonable gold-digger who agreed to a reasonable pre-nup. Heffner is most like a fun 84-year old. She figures she'll live in luxury for a few years, invest the money and be set for life.

      December 27, 2010 at 2:30 pm | Report abuse |
    • bailoutsos

      She use to be Chris Harris, but don't tell Hugh.

      December 27, 2010 at 2:46 pm | Report abuse |
    • Rich

      To say "all" women are gold diggers is ridiculously asinine.

      December 27, 2010 at 2:52 pm | Report abuse |
    • chris

      Awesome! At least her grandfather and Hef have stuff to talk about.

      December 27, 2010 at 3:05 pm | Report abuse |
    • Jeremy

      ALL women are gold diggers – to some degree. If you're blessed with great looks, you aim higher, if you're grenade-ish, you set your sights lower.

      December 27, 2010 at 3:07 pm | Report abuse |
    • Janet

      What surprises me the most is why so many people are outraged by what 2 consenting adults choose to do. Hef's marriage doesn't affect your lives in any way, so why do you care? Get over it and let the happy couple alone. Best wishes Hef & Crystal.

      December 27, 2010 at 3:24 pm | Report abuse |
    • Rich

      All women are not gold diggers but with an age difference of "60" years I would have to say she is. Come on man! Why do people lie so much? I bet if you blew the word hello into her left ear the words " No one home" would come out the right ear.
      Yet another high maintenance with little in return. Hugh is just bored.

      December 27, 2010 at 3:40 pm | Report abuse |
    • tom

      This is just sad. Hugh Hefner engaged again? I do not idolize him so much anymore.

      December 27, 2010 at 4:12 pm | Report abuse |
    • zev

      What a joke.

      December 27, 2010 at 4:31 pm | Report abuse |
    • Babak from LA

      @ Irene ... only if we are lucky:)

      December 27, 2010 at 7:20 pm | Report abuse |
    • sam

      Its the P word ...... her panties and his pockets

      December 27, 2010 at 10:41 pm | Report abuse |
    • Madison

      She should be appointed as moral ambassador of America.

      December 27, 2010 at 11:34 pm | Report abuse |
    • GWA

      Yeah "all girls are gold diggers" and the ones that say it are jealous because they can't provide for them. Reality, girls look at money as status when they see guys just like guys goes for looks. Girls go for guys with money just as guys for looks in women. So with her and hugh it's win win she gets all the money she wants and could even help her friends and family (even cheat on the side with younger and hotter guy) while he gets girl with looks.

      December 28, 2010 at 12:24 am | Report abuse |
    • Mullahrocket

      A gold digger and a dirt old man!
      What a potent combination?

      December 28, 2010 at 3:00 am | Report abuse |
    • Bob

      &h1t viagra-doggyS-allnite F.

      December 28, 2010 at 4:27 am | Report abuse |
    • techtock1

      Yeah. And you're a good reason why women like me won't marry. I love having no one to babysit someone like my former lush of an ex. Life is good now.

      Hope Hef got that prenup tightened. She's not in it for his dashing good looks.

      December 28, 2010 at 6:28 pm | Report abuse |
    • right .

      word.

      January 5, 2011 at 12:37 pm | Report abuse |
    • Carrie

      You say this because you only set your sights on trashy women so to you all women are like that. It's nonsense of course- for example, I wouldn't marry an ass who made stupid remarks like this for a billion dollars. ;P

      January 14, 2011 at 9:30 am | Report abuse |
  9. Peter

    He looks much much much better than the plasticTrump or the cardiac formar Presi, Mr Clinton.
    If he can manage a chick like this one at 84 ... great for him and envy for others.....

    December 27, 2010 at 1:25 pm | Report abuse | Reply
  10. gary

    Which would you rather drive?
    A: a 1958 roadster with a bad clutch, lots of rust,worn paint,missing parts,and seldom starts.
    B: a brand new 2010 shiny red ferrari 599 GTB fiorano.
    Like most men he picked B...... I think he made the right choice.

    December 27, 2010 at 1:26 pm | Report abuse | Reply
    • Bear_Down

      Yeah and she got the roadster!

      December 27, 2010 at 1:35 pm | Report abuse |
    • Sharon

      Gary, you are truly disgusting

      December 27, 2010 at 2:10 pm | Report abuse |
    • Liz

      And she picked the 84 year old car because....she likes bad gas mileage?

      December 27, 2010 at 3:36 pm | Report abuse |
    • crazydebbie5

      Gary go back to your mom and dad's basement

      December 27, 2010 at 3:58 pm | Report abuse |
    • WadesWorld

      Yeah, she picked the old roadster because it came with loads of $$$$ that's it. With the money she could buy herself a ferrari anytime and drive it ;) without letting the roadster know. All girls who are with older guys and I mean really old is usually because they have money. Come on why would they be with them? Let's be real.

      December 28, 2010 at 12:19 am | Report abuse |
  11. alek_martin

    my gawd,,, what is this Hefner thinking about , C'mon, give your granddaughter a break. why pimp with her,,, Give her a life.....
    you can pimp with your magazine.

    December 27, 2010 at 1:27 pm | Report abuse | Reply
  12. IRENE

    Why you guys so put off by women digging in a man's pocket...YOU are always digging in a woman pants..So Shut The F up!!

    December 27, 2010 at 1:34 pm | Report abuse | Reply
    • jackyankee

      you shut up, you would be halfway interesting if you had something else in your pie hole besides a sandwich

      December 27, 2010 at 1:41 pm | Report abuse |
    • Elias

      Difference is what's in her pants is still her, where as his wallet is his possession and not him!

      December 27, 2010 at 7:18 pm | Report abuse |
    • Babak from LA

      Dear Irene; The only men that are jealous don't make enough money ... Nothing wrong with a woman wanting the best for herself and finding the quickest way to get it!! More power to them, if they got it!

      December 27, 2010 at 7:23 pm | Report abuse |
  13. Johnny

    She's not hot but then again I'm not some desperate old man being used by garden tools because of my bank account. I have more respect for Holly and kendra cause I know they were not giving it up to Heff. Don't fool yourself she's after the money in which I hope she gets it all cause Playboy needs to go away.

    December 27, 2010 at 1:36 pm | Report abuse | Reply
  14. jackyankee

    I already had her, she was boring. Sorry to give Hef the bad news.

    December 27, 2010 at 1:39 pm | Report abuse | Reply
    • Ella Jay

      LOL right. i'm sure he has no idea how she is in bed, because they are waiting until after the wedding. it's so excellent of you to help him out this way! :D i say, more power to them. let them be happy. yeah, it's unconventional, but then what is *right and wrong* these days, when it comes to relationships? i'm sure he's got an excellent will that takes care of his children; i'm sure he'll have a fair pre-nup with crystal; and if they make each other happy for whatever reason, all the better. i also am going to guess that with this one (as opposed to his last wife), he probably can continue to have all the parties for which the Mansion is so famous. that is, after all, a large part of who he is, and trying to take that away is a recipe for fail. go hugh and crystal!

      December 29, 2010 at 10:16 pm | Report abuse |
  15. Janet

    She is certainly beautiful, and he has a certain charm and charisma but a marriage with so many years between them is just rediculous. I will however, wish her as many happy viagara filled nights as he can give her. May they be many!

    December 27, 2010 at 1:40 pm | Report abuse | Reply
    • Sharon

      And you would know about her charm and charisma, how?

      December 27, 2010 at 2:33 pm | Report abuse |
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