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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. wow.....

    Ok...we all know its gross she's only been with him for a while right I wonder what Holly is think she was with him for a long time and she wanted to marry him

    December 27, 2010 at 1:11 am | Report abuse | Reply
    • Laur

      That was my first thought too...lol

      December 27, 2010 at 1:54 am | Report abuse |
    • joe

      So your first thought was incoherent? Interesting...

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

      Yeah, I know. She seemed pretty devoted. I feel sorry for Holly.

      December 27, 2010 at 4:57 am | Report abuse |
  2. Kyle

    I'm trying to figure out why he's even bothering with marriage. The article mentions he separated from his previous wife 12 years ago and just this year divorced her. I don't care how anyone lives, but I don't think it's news when this guy 'marries' any girl, no matter how young she is.

    December 27, 2010 at 1:14 am | Report abuse | Reply
    • joe

      So why did you read and then comment on it? It's so wild to me that people do that kind of stuff and then have the balls to say that it's not news. YOU READ AND COMMENTED ON IT.

      Sorry, but capitals were needed there.

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

      It said they were separated in 1998, but divorced this year. A 13 year separation is strange, in and of itself. But I think y'all need to stop measuring their lives against the school teacher in Peoria. He's Hugh Hefner, for crissake, what do you expect from a duck but a quack. Good for him that he can still get the hotties, whatever the enticement.

      December 27, 2010 at 6:56 am | Report abuse |
    • armack

      hey joe , just because one reads a comment doesn't mean he finds it a "news" at all. first of all, you can't say something is unimportant until you can prove it is unimportant, eh? by reading of course..

      December 27, 2010 at 6:59 am | Report abuse |
  3. TheGadfly

    Now I ain't sayin' she a gold digger...

    December 27, 2010 at 1:17 am | Report abuse | Reply
    • LikeItIs

      ...and I'm not saying that he's off his rocker for proposing to someone 1/3 his age.

      December 27, 2010 at 1:48 am | Report abuse |
    • TheGadfly

      You must listen to some pretty terrible music

      December 27, 2010 at 3:29 am | Report abuse |
  4. leia

    yes, she really 'loves him' - who is kidding who????

    December 27, 2010 at 1:17 am | Report abuse | Reply
  5. JCizzle

    Meh, he can afford her.

    December 27, 2010 at 1:20 am | Report abuse | Reply
  6. Nokat

    "She burst into tears" because she's one step closer to his huge bank account.

    December 27, 2010 at 1:21 am | Report abuse | Reply
    • LikeItIs

      No one put a gun to his head.

      December 27, 2010 at 1:49 am | Report abuse |
    • AL

      lol

      December 27, 2010 at 1:54 am | Report abuse |
    • ro

      ha ha, yeah, who says money can't buy me love? nasty nasty, how could she?! no amount of money could make me go there! XP

      December 27, 2010 at 2:06 am | Report abuse |
    • britt

      I keep seeing posts of Playboy being broke. I also thought of poor Holly Madison. I wonder why he didn't go for her? She was kind of pushy about it though.

      December 27, 2010 at 4:11 am | Report abuse |
  7. Scott

    It is like pass the parcel, when the music stops and he snuffs it the current wife at that time takes all!

    December 27, 2010 at 1:24 am | Report abuse | Reply
  8. Jesus of Nazareth

    Umm, it's not made of muscles. There are no muscles in the penis whatsoever.

    December 27, 2010 at 1:30 am | Report abuse | Reply
    • IllinoisMike

      The word, direct from the manufacturer :P

      December 27, 2010 at 7:11 am | Report abuse |
    • jimmy

      There sure are, they are just not like the muscles throughout the rest of the body.

      December 27, 2010 at 7:57 am | Report abuse |
    • Robert Laracuente

      There are absolutely no muscles there. It's actually all skin tissue with alot of empty space in between. This space is constantly full of blood, and when "erection" is commanded, there's a valve that closes a tiny bit on the outgoing side, so the pressure starts building up and voila! Erection.

      December 27, 2010 at 9:28 am | Report abuse |
    • What's Up Doc

      Thank you Dr. Ruth.

      December 27, 2010 at 10:18 am | Report abuse |
    • mike

      my penis has muscles..maybe your boyfriend is a wuss

      December 27, 2010 at 9:59 am | Report abuse |
    • Really

      Look deeper into Crystal's eyes, you'll see her dad died when she was 12 and needs a daddy. Her mom a real estate agent probably needs the finances. She majored in psychology in college in which she didn't finish and instead left school to party at the Playboy Mansion. Zero substance, all looks again = Hef's choice. Good for him, the prenup is the only REAL contract here. Don't insult others who know what real love is.....sorry.

      December 27, 2010 at 1:38 pm | Report abuse |
    • Nicol

      you said it all pal

      December 27, 2010 at 2:33 pm | Report abuse |
  9. Womanof love

    That's crazy he is ...60 years older than her...WOW

    December 27, 2010 at 1:30 am | Report abuse | Reply
  10. ROBBIE

    no doubt he has has a pre nup but good on the guy .........i dont believe in religion but could easily worship Hugh ....what a great life style

    December 27, 2010 at 1:32 am | Report abuse | Reply
  11. Really???

    In 1926, it was common for men to have a wife and several children before 18. With that in mind; he is old enough to be her Great Great Grandfather by a wide margin, and nearly old enough to be her Great Great Great Grandfather. That says it all.

    December 27, 2010 at 1:35 am | Report abuse | Reply
  12. Quincy R

    Lol that's kinda funny, he probly got kids older than her own damn mother, its a nice way to get rich though, like anna nichole, well atleast untill god pulls her file and send karma to get her, I doubt that she will make it to the age of 32 after karma collects, and hopefully heffs not a sucker and left everything to his actually kids and not them hoes

    December 27, 2010 at 1:38 am | Report abuse | Reply
    • LikeItIs

      God sent Karma to get Anna? I thought Karma wasn't from the Christian religion.

      December 27, 2010 at 1:52 am | Report abuse |
    • britt

      Hugh is not an idiot and who said what she is doing is bad?

      December 27, 2010 at 4:13 am | Report abuse |
    • joe

      Good thing that your god is a figment of your imagination, or Hef might actually care what some poor schleck thinks of his lifestyle.

      December 27, 2010 at 4:30 am | Report abuse |
  13. Natalie

    Good example for all the other Girls in America. Boys of their own age are so pathetic. If your a 16 year old Girl any boyfriend should be at least 28 Years old. And have it`s own well paying Job with a very large Bank Account. Have 1 or 2 Sports Cars. And a Large Villa or Bigger with Swimming Pool. Your just a loser without it. This is the Century of the Woman The Century of the Girls! Gimme more, gimme gimme more! Or get out of my way.

    December 27, 2010 at 1:40 am | Report abuse | Reply
    • Stosh

      Hef is supposed to live his life based on what other people consider his "example" to others to be? That is the dumbest thing I ever heard!

      You are a fool.

      December 27, 2010 at 2:33 am | Report abuse |
    • britt

      you watch too much tv.

      December 27, 2010 at 4:15 am | Report abuse |
  14. cloudnine

    One word discusting :P How can a man be so close to death keep making stupid mistakes. To be so worldly rich but so spiritually poor. I feel sorry for him. His soul is so damaged it's sad :( Hopefully before his last breath he will do some good in God's name or else it will be welcome to the toaster OLD POP TART :P

    December 27, 2010 at 1:44 am | Report abuse | Reply
    • Stosh

      Wow, judgemental much?

      You are one sick individual.

      December 27, 2010 at 2:35 am | Report abuse |
    • sassypants

      you know what's discusting?
      spelling disgusting that way.

      (although the story does gross me out)

      December 27, 2010 at 2:41 am | Report abuse |
    • Dave

      You know he will die with a smile on his face.

      December 27, 2010 at 7:17 am | Report abuse |
    • TRS

      Wow.....you can see his soul?? Do me next! What does my soul look like? I know you don't know me, but you don't know Hef either so it shouldn't be a problem, right? Baby Jesus must be sooooo proud of you!

      December 27, 2010 at 8:55 am | Report abuse |
  15. Womanof love

    Do you think her parents and grandparents CARE?? I wonder what Thanksgiving dinner will be like this year, having nothing in common with her but relating with her grandparents...HOW FUNNY!!!

    December 27, 2010 at 1:44 am | Report abuse | Reply
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