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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. Luckyman

    You Think?

    December 26, 2010 at 11:24 am | Report abuse | Reply
  2. blondie

    Dayum!! This guy grosses me out!!!

    December 26, 2010 at 11:25 am | Report abuse | Reply
  3. JuliaInNewMexico

    How can Hef say:
    "I was married and completely faithful for eight years," and
    "I lived a single life, a playboy lifestyle, before and after it, but while I was married I was faithful to it"
    given that Hefner and his previous wife Kimberley Conrad divorced just this year?

    In the eyes of the law, separated or not, you are legally married until the ink is on the divorce decree.

    December 26, 2010 at 11:26 am | Report abuse | Reply
    • midnitejax

      Kinda nitpicking aren't you?

      December 26, 2010 at 11:31 am | Report abuse |
    • Don

      You need to check California law.

      December 26, 2010 at 11:35 am | Report abuse |
  4. Misa

    Don't Hate. Masterbate

    December 26, 2010 at 11:27 am | Report abuse | Reply
  5. Joe Mahma

    If I had his money (or enough of my own) I'd be doing the same thing.

    December 26, 2010 at 11:28 am | Report abuse | Reply
  6. Playboy

    Couldn't he just hire someone to work on charlie there? Does he need all this formality?
    At least it would be honest. To much BS.

    December 26, 2010 at 11:29 am | Report abuse | Reply
  7. Paul

    Hugh, he be BANG'N !!!

    December 26, 2010 at 11:30 am | Report abuse | Reply
    • saywaaat

      doubt that very much.cuddling maybe.

      December 26, 2010 at 11:43 am | Report abuse |
  8. RS

    LOL you all are so hateful towards these two. Talk about a bunch of envious clowns. Especially the WOMEN on the board. It's hard for a woman to accept another is better than her.

    December 26, 2010 at 11:32 am | Report abuse | Reply
  9. GG

    Am I the only one that is thinking about what Holly must be feeling right now??? Geesh, she spent five years with Hef and couldn't get him to commit, and now he's marrying Crystal. BURN!!! Speaking totally superficially here, I do agree that Crystal is more physically attractive than Holly, Bridget and Kendra, but I still can't believe that he's actually going to tie the proverbial knot. I ASSUME there will be a MAJOR PRE-NUP. Also, Ryan Seacrest better make sure things are OK with his gal, Julianne Hough becasue Crystal and Julianne look like one in the same! LOL! Happy Holidays everyone!

    December 26, 2010 at 11:34 am | Report abuse | Reply
    • Don

      Holly isn't the brightest bulb on the tree. Fine for a bimbo to travel with but not for a wife. Maybe this one is more intelligent and her body parts might be real.

      December 26, 2010 at 11:42 am | Report abuse |
  10. Sherm

    24. Nice.

    I bet that Hollie chick is mad. She tried to trap him for years.

    December 26, 2010 at 11:34 am | Report abuse | Reply
  11. Jordan

    BY THE NUMBERS:

    3 – The age of Crystal Harris when Hef married Kimberly Conrad.

    12 – The age of Crystal Harris when Hef and Kimberly divorced.

    27 – The number of years between Hef's first marriage and the birth of Crystal Harris. (It's entirely possible that Crystal's parents had not even been born as of the first marriage).

    60 – The age of Hef in 1986, when Crystal was born.

    December 26, 2010 at 11:35 am | Report abuse | Reply
    • p.bear

      Wow!
      He is the man!

      December 26, 2010 at 5:12 pm | Report abuse |
  12. Cynthia Rutherford

    come on Hef..you van not think this girls in love with you. It is your MONEY.Stevie Wonder can see that. And girl all I can say is how creepy n gross is that to think of being with someone so old.OH forgot... MONEY. I SAY GROSS.GODD LUCK!!!!!!!

    December 26, 2010 at 11:35 am | Report abuse | Reply
  13. Stephanie

    Poor Holly, she was waiting for Hef to marry her. She finally left him after 6 years together.

    December 26, 2010 at 11:36 am | Report abuse | Reply
    • God

      Stupid girl. She thought she would change him, that she knew something all the others did not. Two words for Holly: "bye bye."

      December 26, 2010 at 12:21 pm | Report abuse |
    • Sherm

      And then she had to take up with a street magician.

      December 26, 2010 at 5:15 pm | Report abuse |
  14. Cynthia Rutherford

    come on Hef..you can not think this girls in love with you. It is your MONEY.Stevie Wonder can see that. And girl all I can say is how creepy n gross is that to think of being with someone so old.OH forgot... MONEY. I SAY GROSS.GODD LUCK!!!!!!!

    December 26, 2010 at 11:36 am | Report abuse | Reply
  15. sam wardName*

    Does Hugh really think these girls love him, they love his money and the stardom they get from being with him.24 yrs. old with an 84 yr. old REALLY. I bet these girls make their daddys proud. Money shores are what they are. Kudos to you for banging them Hugh. You are the man.

    December 26, 2010 at 11:37 am | Report abuse | Reply
    • Neal

      I bet her mother divorced her father so there is no daddy to make proud. She probably learned that from her mom – marry money, divorce, and keep the money.

      December 26, 2010 at 12:13 pm | Report abuse |
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