Hugh Hefner on His Breakup: 'I Was Road Kill'

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Hugh Hefner Pictures: Hugh Hefner on His Breakup: 'I Was Road Kill'
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Hugh Hefner is opening up about his emotional breakup with main girlfriend Holly Madison.

"I had planned to spend the rest of my life with Holly," the Playboy mogul told Us magazine, explaining that after their falling out, "I was road kill a couple of weeks ago."

Hef, 82, admits that he and Holly, 28, were unable to have kids, and that played a role in the split: "We tried to have a baby earlier this year and it didn't work out," he said. "She became very depressed."

Last month Hef told the mag: "She is still my girlfriend," he said. "Now will that last? I don't think anything lasts forever."

Published 10/9/08 by the Insider

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Comments (43)

  • Great Grandfather Hef,

    Its time to grow up. You should have settled down at 70. Holly needs a healthy family man.
    anonymous anonymous 10/9/08 Reply
     
  • She just use him to became a big star what a loser, And now she is a star she don't care anymore for old gizer.
    Shqipe 24 Shqipe 10/9/08 Reply
     
  • what about with other 2 girlfriend that he had?
    Shqipe 24 Shqipe 10/9/08 Reply
     
  • I loved Holly and I thought she was the most sincere. Shame on you both for not making it work!
    anonymous anonymous 10/9/08 Reply
     
  • Hef, the rest of your life could only be a few more weeks!! There is NO fool like an old, rich fool!!!!! She is no better than a whore for hanging with him anyway. C'mon, no rational person would actually think she would want a wrinkled up geezer old enough to be her grandfather. It's the money, honey!!
    anonymous anonymous 10/9/08 Reply
     
  • nothing lasts forever in hollywood
    anonymous 1733 ZhenF 10/9/08 Reply
     
  • It's true, it's all about the money. You wish you could be Holly. When you know the opportunity and the money are out there waiting for you, your ass would have done the same ...becoming a whore...hahaha.
    anonymous anonymous 10/9/08 Reply
     
  • I think she really loves him. Hugh love her, it does not matter the age. I think they should stay together even if they can't have a baby. The should try to work thing out.
    anonymous anonymous 10/9/08 Reply
     
  • imagine seeing his naked ?! Man, not enough money in this world for me ...see more
    Trujrzygirl 27 Trujrzygirl 10/10/08 Reply
     
  • Their ages are made up of the same numbers in reverse, which is the most fascinating part of this article.
    anonymous anonymous 10/10/08 Reply
     
  • Please work it out! The Girls next door is wonderful and they are family! Holly and Hugh belong together.
    anonymous anonymous 10/11/08 Reply
     
    • Shut up its all about the money, u think that old wrinkly uncomfortable spot of his would last long in the other place. Its all about money, welcome to reality
      anonymous anonymous 10/13/08
       
  • i think that hef needs to stop dating these youngs girls he needs to forget about dating and live his life and these young girls dont want him because of him they want his money
    anonymous anonymous 10/12/08 Reply
     
  • Holly seemed so sincere and devoted in her "love" to Hugh. I don't think it was fair to her that he wouldn't marry her. I know how badly she wanted a family, as all women do.
    anonymous anonymous 10/13/08 Reply
     
  • So sorry to hear about the break up. Conception doesn't just happen for all people my sister and her husband went through a year of fertility treatments to only end up divorced but after a year they reconciled and surprise surprise my neice was conceived the old fashion way. Best wishes to both Holly and Hef, I hope you both can find some happiness.
    erica
    anonymous 5 emorgan 10/14/08 Reply
     
  • I hope everyting works out for the best for both of you. good luck!!!
    anonymous anonymous 10/15/08 Reply
     
  • Oh C'mon!! Quit telling people what to do and just let it be! It didnt work out because the age and the baby situation..she loved hef! If you watched the shows..while everyone was out partying, she was going to bed with Hef!
    anonymous anonymous 10/15/08 Reply
     
  • Also...if Holly was in it for the money...she would have been gone along time ago when she became a big star....read the facts! they were in love!!!!!!!!!!!!!!!!!!!!!
    anonymous anonymous 10/15/08 Reply
     
    • Big star?
      anonymous anonymous 10/27/08
       
  • I think that it is a good thing. There is no reason a 28 year old girl should have a baby with a man that is in his 80's. The child needs a father in his life. I hope Holly finds someone that has as great of a personality as she does! Good Luck Holly!
    anonymous anonymous 10/17/08 Reply
     
  • i think that holly felt desperate because she wanted to have kids, but they should try other methods and holly should not leave hef because of him she become a star and he lover her.
    i think holly owns a lot to hef, she should think about that!!
    anonymous anonymous 10/21/08 Reply
     
  • you holly
    anonymous anonymous 10/21/08 Reply
     
  • if they really want kids there are always other ways to make it work, But the age difference is a very big reason why they shouldnt. i love holly, but her relationship with hef that makes me think she is in it for the money she would get from the kid after dear OLD daddy dies, and lets not mention the fame.
    anonymous anonymous 10/24/08 Reply
     
  • i think Holly should go back to hef and they should get married
    anonymous anonymous 10/27/08 Reply
     
  • I think she wants to have a baby because she know the money is there!!! Uhmmmmm! she is not stupid!
    Who wants to have a baby with that old and ugly guy?
    The only beautiful thing he has " The Money",
    Of course she is depressed!!!!!
    anonymous anonymous 10/27/08 Reply
     
  • It's a TV show -- it's not real. The comments posted here are hysterical. I'm always surprised that people really take this stuff seriously.
    Annabel
    anonymous anonymous 10/30/08 Reply
     
  • The reason I think she wants a child, is to get more money. C'mon, I don't believe one bit she is sexually attracted to a man that looks like her grandfather, if she loved him she wouldn't bare to see him with other woman. That is why I think she is a lesbian. All three of the girls are money hungry, and are just using Heff. Heff is rich, if these girls allow him to use them , that is what will happen. He should date and marry Kendra's mom. I don't think there is a problem if there was a 20year difference, but nooooo he is too old for the girls.
    MobenahA 10 MobenahA 11/4/08 Reply
     
  • Thank God! She gave new meaning to "dumb blond". She is as plastic, ugly, fake and dumb as he is old and wrinkled
    anonymous anonymous 11/6/08 Reply
     
  • I believe that holly was in love with hef but not being able to have children with the man you love is heart breaking and holly has made the wisest choice for her happiness.
    anonymous anonymous 11/7/08 Reply
     
  • aww you guys made the cutest couple ever i love heff and holly she was my favorite along with bridget and kendra! I really did think you guys would last forever! why did you just adopt a little asain baby or something lol!
    anonymous anonymous 11/9/08 Reply
     
  • i think holly was truely in love with hef. i watch the show faithfully and she was so happy with him. i do think hef and holly should get married, he did it once before and i think holly and hef deserve eachother and i think they would last till death do them part. the can work on a child longer then a month even consider adoption. now kendra on the other hand is only there for the money, she is so fake you can tell just in her laugh..
    anonymous anonymous 11/10/08 Reply
     
    • I agree. Hef was just the diving board into the pool of money, athletes and rappers.
      anonymous anonymous 11/11/08
       
  • With all thier money and resources, they couldn't just adopt a baby or buy one! If he keeps adding names to his will, everyone will come away with $100.
    anonymous anonymous 11/11/08 Reply
     
  • WOW... kinda funny how now that Hef can't get her prego so that when he passes away she can get a load of his money... she doesn't love him enough to stay with him anymore and moves on the the next guy with money... B****!!
    anonymous anonymous 11/11/08 Reply
     
  • Aside from all the age stuff, I think Hugh is a great man. He is someone to be looked up too, he started a revolution, and opened up a magazine in an era which was anti-sex. Maybe Holly saw what many people don't see. The true Hef. She feel in love with him for him, age sometimes really is not that important. Being so young, and not being able to have kids must of hurt her, if she wanted the money she would have stayed with him.
    anonymous anonymous 12/31/08 Reply
     
  • Maybe I am in a world of my own but, reading the comments below is stunning. What a bunch of judgemental people. I personally think that Hef seems to be a very soft spoken, kind and gentle soul. Holly is as kind and gentle. Only they know what is up and it is only their business.
    anonymous anonymous 1/3/09 Reply
     
  • you got it right and gave me a good laugh
    anonymous anonymous 2/7/09 Reply
     
  • CAN I BE PLAYBOY 2 YES OR ON
    anonymous anonymous 2/15/09 Reply
     
  • hef needs to sit his old ass down. he dont need anymore kids he to old for that. he aint nothing but a pimp and those grls aint nothing but glorified hoes. if it wasnt for the money they would never have looked at him twice. im glad they broke up and now holly can have children and live life with someone closer to her age.
    anonymous anonymous 2/27/09 Reply
     
  • shame on hef why doesnt he have a girlfriend closer to his age instead of a 90 year age diffrence :/
    anonymous anonymous 3/2/09 Reply
     
  • As a father of two girls, I must say this is the most rediculous thing I've ever seen ! Sure, all of these girls are/were in it for the money and glam.We all know why hef is in it and I personally doubt his motive is ever love. The thing that bugs me most I guess is that in our society this kind of garbage has become the rule rather than the exception. I'll bet these girl's fathers are really proud of them.
    anonymous anonymous 3/14/09 Reply
     
  • i think its time for you to move on grandpa!!!!
    anonymous anonymous 3/28/09 Reply
     
  • You can hardly say 'he needs to get out and live his life'
    He's in his 80's an he's managed to surround himself with hundreds of beautiful 20 something women
    I'm sure he can't think of even one thing he'd rather be doing with his life
    anonymous anonymous 3/29/09 Reply