Hugh Hefner wants Holly Madison back

Hugh and Holly on 8/28/08. Credit:
Hugh Hefner’s new trio of barely-legal blondes must not be intellectually or emotionally stimulating enough for the geriatric bachelor. The 83 year old is still pining for lost love Holly Madison, who he called “The love of my life” in a recent interview:

It has been several months since Hugh Hefner and his former flame Holly Madison went their separate ways, but it seems the 83-year-old men’s magazine mogul still has super strong feelings for the 29-year-old pin-up. Hef told Jason Binn, editorial director of Niche Magazine’s Los Angeles Confidential, in his debut issue that he’d welcome Madison back with open arms because she is still the “love of his life.”

So where does that leave things with his new top squeeze Crystal Harris?

“How serious, and intimate, and important that works out to be, well we’ll have to wait and see because it’s only a couple months old,” Hef said in the upcoming issue, which hits the stands on May 1.

So even though Hef’s heart is still hoping for Holly, it doesn’t look like a reunion will happen any time soon.

“I loved my time at the mansion and think the world of Hef,” Madison told Tarts in response. “There comes a time in everyone’s life where they need to go their own way.”

And although Mr. Hefner still considers himself the ultimate playboy and has lived (and continues to live) a life beyond what most men could even dream about, he has two prominent regrets — his two marriages (the first to Mildred Williams in 1949 and then to Playmate Kimberly Conrad in 1989 — to whom he’s still married) and taking his empire public.

“I think the company would have been more closer to home if it had remained a private corporation,” Hef admitted.

[From Fox News]

Doesn’t it sound like Hef isn’t getting any from Crystal? He said “How serious, and intimate… that works out to be, [with Crystal] well we’ll have to wait and see.” She’s a 22 year-old San Diego State co-ed and in the only interview I’ve seen with her she came across as vapid and kind of dumb. I assumed she was the one keeping Hef company as the alternative, his two 19 year-old ex con twin “girlfriends”, conjure up all sorts of unsettling images when you let your mind go there. It looks like all of Hef’s arm candy is just for show this time around. No wonder he misses the girlfriend who stood by him for so long, but she’s moved on to other things. In an interview with In Touch last October after the split, Holly made it clear that she’ll never be with another man that much older and that she’s not going to reconcile with Hef. You can tell from her statement here that she wouldn’t consider it, either, as she said “There comes a time in everyone’s life where they need to go their own way.”

Hef saw Holly for the first time since their split at his birthday party earlier this month. She was cordial but mentioned that she was there for the sake of their reality show. It’s kind of sad for Hef that he’s still chasing super young tail at that age and missing the one that got away.

Hugh Hefner is shown below with his new girlfriends on 3/21/09. Holly Madison is shown at US Weekly’s Hot Hollywood party on 4/22/09. Credit:

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18 Responses to “Hugh Hefner wants Holly Madison back”

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  1. guest says:

    they should get back – exclusively.

  2. Obvious says:

    AS weird as it was I loved them together. She honestly cared about him, and he about her.

  3. Kayleigh says:

    I wonder what pissed her off so much to be so resentful towards him?

  4. Michelle says:

    Holly was my least favorite of the Girls Next Door (Bridget FTW!), but she’s still infinitely classier and more attractive than any of Hef’s trashy new chicks. And you could tell she and Hef truly did care for one another. Kinda sad, even though the thought of being in a relationship with a dude old enough to be my grandfather creeps me out.

  5. hotmilfchocolate says:


    poor puffin!

  6. maritza says:

    I guess Holly realized Hef would never marry her or get her pregnant so why stay there since he still had all these women around him. Holly deserves better, she is a sweet and lovely woman.

  7. Case says:

    She would be stupid to go back to him. She has already wasted to much of her life with him.

  8. ThatBKChick says:

    Holly was the HBIC…but Hue would not and will not submit to a manogamous relationship…he has truly embedded or indoctrinated the would “Playboy” to the fullest defintion…she knew this going in…You can’t make turn a househusband/Whoremogner otherwise…I have not an ounce sympathy for this situation. These women know what they are getting into when they sleep with Grampy….SMDH!

  9. HEB says:

    I think his new girls probably aren’t following the ‘rules’. Lets face it–Holly did EVERYTHING for him, from getting him drinks at the club to helping him out of bed in the morning, and when she couldn’t do it, Bridget was right there to do it in her place.

    Lets face it, Hef is going back to the same strategy as when he formed the party posse after Kim left him…then he got Holly and Bridget and he got spoiled! (Kendra was fun and kept things hot, I don’t think she was fetching drinks and arranging back pillows though). He’s a lot older now and the average desperate blonde isn’t going to cut it!

  10. raven says:

    I had no idea Hef was still married. I’m not sure why they are not divorced (maybe it would cost him too much) but he was a fool not to do whatever it would take to keep Holly. I was never that fond of her either, but she did stand by him. When your image or ideas get in the way of your own real happiness, maybe it’s time to reassess

  11. A_G says:

    Too little, too late. Hef let a good one go …

  12. dan says:

    “I wonder what pissed her off so much to be so resentful towards him?”

    i hope that statement was riddled with sarcasm because otherwise its kinda obvious to see what would have pissed her off. i remember reading in an interview that she wanted to have kids with him and have a settled life but he didnt want that. and now look whats happened. she definatly deserves better.

  13. adrian says:

    This is so sad… hopefully all the “playboy” men learn from him. He will now die happy outside, but lonely and miserable inside. I didn’t like her, but she truely loved him and obviously he loved her…. sad sad sad

  14. Sid says:

    Absoluty not. She would just be a chick on the side the rest of his life.
    Don’t Heff have 1 grown daughter that run his business and 2 boys. He would have nothing left to give her.

  15. j. ferber says:

    Hefner also has a grown son from the first wife. I believe he’s gay, so either he chose not to get involved in Playboy for whatever reasons or he didn’t fit the Playboy lifestyle and was not invited to operate the empire. I agree with Case that Holly wasted enough time with Hef. And how lousy of him to say he regrets his two marriages, especially since his younger kids are only 17 and 18. But, to take it in stride, he’s a self-involved, superficial guy himself (has to be, given his life choices).

  16. nanster says:

    Hef is old and delusional and I think Holly Madison must be a very good actress. She may have cared for Hef because he was a great springboard for her career, but the two of them sharing a great love? Ha – I think not. It’s amazing what an incentive money and fame can be, and unfortunately for him, “Gramps” just doesn’t get that the joke was (and continues to be) on him.

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