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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. Tiffany

    I'm 27 and I hate when a guy over his late fourties hit's on me. It's gross. Most women feel this way. Two reasons for a woman to get with a guy that's decades older. 1. You fall in love slowly. You get to know him in a non romantic way and fall in love. Or he's rich. Okay there's one more. If he's like superhot. I mean with the PX90 thing I've seen a 50 year guy with an AMAZING body.

    December 27, 2010 at 1:48 pm | Report abuse | Reply
    • Babak from LA

      It is the girls that hit on us ... not the other way around. Well in Los Angeles:)

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

      By they way how did you see the 50 year old's body .... I thought you said it was gross. Was it in a Bently?

      December 27, 2010 at 7:31 pm | Report abuse |
  2. lula

    What moral decay. Standards have certainly gone out the window. Mr. Hefner is certainly the devils advocate. We live in a society that accepts almost anything as okay. Think, would you want this lifestyle for your son or daughter..

    December 27, 2010 at 1:48 pm | Report abuse | Reply
    • JackA

      What society are you living in?

      December 27, 2010 at 3:04 pm | Report abuse |
  3. nav

    Both are adults & know what they are doing. If they are Happy or seem to be Happy then I am happy for them. But I don't think this will last. Heff time to call it man, there is more to life than just keep marrying.

    December 27, 2010 at 1:49 pm | Report abuse | Reply
    • Richie P

      A 24-year-old bimbo is not an adult.

      December 27, 2010 at 2:42 pm | Report abuse |
  4. ChaCha

    LOL!

    December 27, 2010 at 1:51 pm | Report abuse | Reply
  5. Ralph in Orange Park, FL

    There are worse ways to die.

    December 27, 2010 at 1:52 pm | Report abuse | Reply
  6. bookenz

    Wonder what they have in common. Oh yeah, soup. They both like soup.

    December 27, 2010 at 1:54 pm | Report abuse | Reply
    • Jamie

      " We love talking and not talking. We could talk or not talk for hours"- Way to quote Best In Show, Man.

      I actually went to high school with Crystal. She wore less make up then, obvi.

      December 27, 2010 at 4:41 pm | Report abuse |
    • Adit(India)

      Ha.. ha love that one. Come to think of it Hugh sure is an inspiration for other divorced guys effectively demonstrating that if one tries hard enough and earns the dough, then one can get married to a great girl.

      December 28, 2010 at 5:57 am | Report abuse |
  7. get a job

    LMFAO..........

    December 27, 2010 at 2:06 pm | Report abuse | Reply
  8. Richp, Easton, Pa

    He was admired in the 60's, 70's, 80's, 90's and into the 2000's, You all know you'd sell your eyeteeth for the view he has and where he lives, go heff and enjoy.

    December 27, 2010 at 2:13 pm | Report abuse | Reply
    • groovygoober

      Uuuuh, no, I would not.

      December 27, 2010 at 2:31 pm | Report abuse |
  9. Sharon

    I give it . . . . 3 years. If he doesn't kick the bucket first. (Which I'm sure is exactly what she's hoping for.)

    December 27, 2010 at 2:14 pm | Report abuse | Reply
  10. Sharon

    Major ewwwwwww factor

    December 27, 2010 at 2:15 pm | Report abuse | Reply
  11. Paul

    How is it that Hugh gets engaged to someone 64 years his junior and no one really bats an eye, yet a man in his 40's can get vilified and called a pervert for dating a woman who might be in her early 20's? Women, often frown at older men dating younger women, but if you look at Larry King, Donald Trump, Celine Dion's husband, and I'm sure a plethora of other wealthy men, it seems like it's acceptable by women as long as they are affluent in stature. Maybe I'm wrong, but I've seen plenty of women get hateful when they've seen couples that fit that description.

    December 27, 2010 at 2:18 pm | Report abuse | Reply
    • groovygoober

      Because it's only disgusting when they aren't filthy rich...lol.

      December 27, 2010 at 2:32 pm | Report abuse |
    • Liz

      Paul, you said that no one is batting an eye at this – have you read the comments to this story? Just about everyone finds this disgusting. A man in his 40s dating a woman in her early 20s is no less gross. It's creepy when people date that much younger – and is evidence of self esteem issues.

      December 27, 2010 at 3:39 pm | Report abuse |
    • true

      It is disgusting and wrong either way. However, if a man feels he must date a woman who could be his daughter and obviously himself does not have youth/age equality to offer, then he obviously should have *something* to offer to make this a fair proposition to the woman who foregoes dating other man of appropriate age to some ugly old geezer. So the fact that men like Larry King do realize this and have the means to offer a woman security, fame, and financial stability in exchange for her youthful company and for her accepting his age and ugliness makes it somewhat ok, while men who feel that younger women should be dating them just for the heck of it are simply pathetic and ridiculous.

      December 27, 2010 at 7:28 pm | Report abuse |
    • Babak from LA

      Dear Paul; I would like to argue and give reasons to explain why you are wrong .. unfortunatly I can't because you are right!!

      December 27, 2010 at 7:58 pm | Report abuse |
    • Babak from LA

      @Liz; It is called pay back! you see some guys work their butt off in their 20s, 30s and 40s to make it. There are they same guys that no one took seriously .... that is where they get there drive from ,partially. If is interesting when the tables are turned ... There a certain level of self-satisfcation that come with that .... And at the end everyone gets what they wanted ... so what is wrong with it?

      December 27, 2010 at 8:02 pm | Report abuse |
    • Anjaba

      @Liz – How is it gross if a 40yr old dates a women in her 20s??? My father just retired from the military, PT for 23 years straight and he is in better shape than half of the 20 something year old MTV/McDonalds generation of today! Please. Also, all you women who say it's gross and I just want a guy that makes me laugh blah blah, haha, you probably lay there on your back in bed and are boring as hell. Talk about how HE is insecure?? Wake Up. You only live once!!

      December 28, 2010 at 3:21 am | Report abuse |
  12. NM

    This wedding will never take place! You can say blonde bimbo? I'm sure her parents are just thrilled for her... NOT!!!

    December 27, 2010 at 2:19 pm | Report abuse | Reply
    • Janet

      Her father died when she was a young girl.

      December 27, 2010 at 4:35 pm | Report abuse |
  13. Danny K

    Well I am 85 years old and i recently got married to a 19 year old girl in philipines... i went to philipines..got married and brought her back home here in Florida :)

    December 27, 2010 at 2:26 pm | Report abuse | Reply
    • Sharon

      Danny, what do you think she wants exactly? A green card, maybe? Hmmmmmm???

      December 27, 2010 at 2:34 pm | Report abuse |
    • zzk

      This is not a marriage, this is called buying each other package. Deal done.

      December 27, 2010 at 2:48 pm | Report abuse |
    • hottietottie

      umm...i highly doubt this

      December 27, 2010 at 3:45 pm | Report abuse |
    • Babak from LA

      Danny more pwer to you both. You will get to enjoy the rest of your life and even have a few more years because of it. she gets to have opportunities she could not have otherwise ... Good luck! Happy Holidays!!!

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

      !!! Awesome !!! More power too you! Have fun. Better than all these boring people sheep that just live their lives according to what society deems ok when society is in fact more f'ed up than anything else, haha.

      December 28, 2010 at 3:23 am | Report abuse |
    • maya

      I don't think you are 85 and I do think that you're making this up, especially since you're using smiley faces (don't know many 85 year olds that can get that detailed with the Internet).

      December 28, 2010 at 11:36 am | Report abuse |
    • Alex

      You're sick Danny. Getting a young slave for free in the guise of marriage.

      December 28, 2010 at 9:09 pm | Report abuse |
    • George Moore

      I think that is really great and also fantastic! I am 83 years old. My girl friend is 39 years old. I am going to propose to her.
      Ain't nobody's bizness but R own. We can't live our lives worrying about what people think. It's our life not theirs. ?What do they know anyway? It's 'tween us!

      January 13, 2011 at 8:11 pm | Report abuse |
  14. Nicol

    vanity at its best form...oh boy...lol

    December 27, 2010 at 2:31 pm | Report abuse | Reply
  15. tiredodacrap

    Gold Digger, and Pathetic Old Man...Is this news???

    December 27, 2010 at 2:35 pm | Report abuse | Reply
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