Why didn’t Hugh Hefner marry Holly Madison?

Holly Madison reportedly wanted to marry her boyfriend of six years Hugh Hefner and have his babies, but in 2008 he publicly announced that he wasn’t the marryin’ kind:

“I love Holly very much, and I think we’re going to be together for the rest of my life. But marriage isn’t part of my puzzle. It’s not a personal thing – I just haven’thad much luck with marriages.”

Soon after that, the broke up, Holly briefly dated Criss Angel Mindfreak, then moved to Vegas for a permanent spot on the burlesque show Peepshow. She also got her own reality show Holly’s World, which chronicles her life after Hef.

On a recent episode we watched Holly react to news that Hef was engaged to 24-year-old Crystal Harris, and she reportedly hi-tailed it to the Playboy mansion to tell Hugh Hefner how she felt about it. She also spoke liberally with the press.

She told Life & Style (via The Huffington Post):

“I’d like to see Hef settle down. I just want it to be with the right person, and I feel like he’s making a hasty decision. I’m not sure Crystal is the best thing for him.

“Crystal hasn’t been around very long – she’s a mysterious character. No one knows much about her. Plus, she’s very young, probably too young to settle down. I’ve seen a lot of girls try to date Hef, and some have ulterior motives. I don’t think it would be a bad idea for him to get to know her a little better. I think it’s possible Crystal could break Hef’s heart. They could end up divorcing, and she could take half his money.”

About what happened when she confronted them at the mansion:

“I told them that I wish them the best and that Crystal had better not do him wrong or else I’ll kick her butt. It was definitely awkward.”

What exactly did Hugh find with Crystal in a few months that he didn’t find with Holly in six years (or with other women for nearly 80 years?) It’s one of those mysteries of life.

Photos by: WENN.com

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  • sara

    I think dementia is setting in & the ho is taking advantage of the old geezer.
    His kids should put a stop to his crazy antics before he gets taken to the
    cleaners. He’s making a fool of himself. This sounds like Anna Nicole special. & Howard Marshall Yuck. You have to have a strong stomach for these old men

  • Donna

    I really think that Hef’s engagement is out of a sub-conscience fear of being alone as he also fears his mortality. I watched the episode in which he and Holly finally talked. You could see the love was still there, but also the hurt in Holly’s eyes. He said he was not the marrying kind, through away the true love of his life because of it. I do not see that same connections with Crystal. Mary O’Connors, Hefs assistant, really showed that he is marrying not because of love. But because Crystal fits what he needs at this time, it is not love. I had become a fan of Hef’s because of the true love relationship he had with Holly, it showed the loving side of him. But this engagement shows he is back to his player ways, needs a child to feel young again.

  • abcdramaqueen

    He’s more like a dad to the girl’s! I don’t think he could ever keep up with any of them in the sack, obviously Holly could have handled this and stayed with him had she gotten a ring! Hef took Holly’s love for granted thinking it would always be there! Its the classic story of a serious relationship, the break-up, then the next one in line is the one!

  • Kari B.

    Holly was not in love with Hef. She want to marry to get half (divorce) or all (death). She wanted his children for guarenteed money. He likes these young girls b/c A.) he can B.) They’re young and “hot” (eyes of the beholder) and C.) They do whatever he wants b/c they are gold diggers and he’s got the money to spend on girls that go to bed when he says so and are molded to fit his fantasy (blond w/ boobs). These girls know what they’re doing and so does Hef. If he’s willing to marry then he knows the risks. Everyone gets what they’re after. I couldn’t do it.

    • jenny v

      Hol made a living with her own money, and went off doing her own thing, and still wanted to marry him, so she is not the gold digger in this situation! crystal is

      • AKM

        EXACTLY! Thank you, Jenny!

  • jb

    Who ever reallys knows why….but I DO think that timing has alot to do with why he’s marrying Crystal. I believe life reality is setting in. Keep in mind that we really do not know the terms of their impending marriage. How do we know that Crystal has the potential to get everything? Perhaps he has agree to set her up with a comfortable amount but not simply give all away to her carte blanche. Perhaps he offered Holly the same thing and when it wasn’t enough, she left instead. We just don’t know.
    In regards to Holly, while I think she liked Hef and cared for him very much, I don’t think she truly loved Hef in the couple sense. I believe she enjoyed working her way to number one, and I believe she like the power of the role of his number one, but I don’t believe she really liked him. And I have a feeling Crystal does truly enjoy him. Men know the difference….no matter how old.

  • Tami Fabian

    if he was on social security do you think there would be a catfight? pleeeeease, it’s all about the money. what better for a gold digger to find a rich old man with one foot in the grave? give me a break, get real.

  • Vanessa

    I am not sure, as none of us can be, but I believe that it was all about the timing. It was pretty obvious that he loved Holly. He made the choice to say he would never get married again, so she left…and when she did I think it finally hit him that he couldnt live like this forever…and so in the end it is just him not wanting to be lonely, and he is probably tired of having so many girls getting famous for pretending to love him. I personally think it is a sad life to take advantage of someone that is hurting. But thats what these girls do.

  • Lala

    I wouldn’t feel too bad for Hef. He uses them as much as they use him. It’s a mutual thing, they’re all a bunch of users.

  • ziz

    personally i could never agree to get married for a guy who’s at the age of my grandpa money can’t do that to me,but girls(hot sexy tall fame seakers clothe lovers) could do anything to get what they desire and huff’s got that he(money)makes them happy cz no wonam-NO WOMAN- could look at her grandfather as a lover i mean look at his wrinkels and maybe he’s close to death so they can get advantage of half the money and get famous.

  • AMY


  • Harlee Jo

    It was sooo obvious that Holly genuinely loved Hugh. I will never understand how men can be with one woman like 10 years and never even attempt to marry her then meet a another woman and marry her in less than a month?