Holly Madison and Kendra Wilkinson respond to the news of Hef’s engagement

Two of Hef’s last set of girlfriends, Kendra Wilkinson and Holly Madison, have responded to the news of his engagement to 24 year-old Crystal Harris. Kendra was more congratulatory, which makes sense considering that her arrangement with Hef was more business than anything serious. Holly said she was surprised and that she had a hard time saying anything about it as she was afraid it wouldn’t sound sincere. Holly was hoping to marry Hef herself, and even shelled out her own money for IVF treatments trying to get pregnant back when they were together. When Hef’s sperm just sat there and shrugged, Holly packed up and left, supposedly realizing that she wanted more out of life. She doesn’t sound completely at peace with the news that Hef is marrying the next one to come along.


She had to share Hugh Hefner with two other ladies, but Kendra Wilkinson-Baskett wasn’t shocked to hear that Hef had decided to get engaged to Playmate Crystal Harris.

“I’m not surprised,” Kendra told Marc Malkin of E! Online. And as Malkin reports, Wilkinson-Baskett though this might go down all the way back when Hefner divorced Kimberley Conrad in September, 2009 — Hefner and Conrad had been separated since 1998.

“And then I heard how much he loves Crystal and how he looks at her,” Kendra said. “You can just tell there’s a whole other meaning of love in him. I feel like she’s the girl for him.”

Kendra’s sentiments contrasted completely with those expressed by Holly Madison, who was at one time Hef’s number one girl.

“I’m very surprised,” Madison told Malkin. “I have a lot of different feelings on it. I don’t just feel one way. I kind of didn’t want to put a generic statement out there like ‘Congratulations!’ because I felt everyone would see through that.”

Madison left Hefner in 2008, when she found out he couldn’t have any more children at his advanced age.

“I want to be with somebody I can have more of a future with eventually. Hef and I can’t get married and have kids,” she said at the time “So it was fun while it lasted but it wasn’t right for my old age. I got too old for Hef.”

[From The Huffington Post]

Last week we heard a rumor that Holly was upset that Crystal succeeded where she failed, and it seems like that was true. So did Holly just break up with Hef hoping he’d propose? It must be hard out there when you’re hustling and hosting bikini parties. Holly finally scored her own reality show but it took her a while. Meanwhile Kendra is taking tips from the Kardashian school of famewhoring. She’s got her own sex tape, reality show, and exaggerates her marital problems to earn tabloid covers followed by more headlines when she denies the stories she planted. Lord knows what happened to Bridget.

Holly is shown on 12/31 and 12/18/10. Kendra is shown on 1/5/11. Credit: WENN.com

This dude is younger than Hef by about 20 years.





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36 Responses to “Holly Madison and Kendra Wilkinson respond to the news of Hef’s engagement”

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  1. teehee says:

    too old for Hef… lol too mature for that adolsecent centennial

  2. Lisa Turtle says:

    I actually feel sorry for Holly. To delude yourself into being attracted to a man 60+ years your senior, to put in the work for 4 years, the bathing, the diapering, the viagra, only to be rejected by him and then replaced with a younger woman who he wants to marry. Wow. Hef should at least offer to pay for Holly’s therapy.

  3. k says:

    I actually suspected that Hef was more hurt by Kendra’s exodus than he cared to admit, and this engagement is payback.

    Anyway, don’t care .. they’re all hos.

  4. Kiks says:

    I feel really bad for Holly. I think she really loved Hef (God knows why…)and she thought she was the one that was going to “change” him and get him to settle down. I wish her well and hope she finds someone who loves her as much as she loves them.

  5. brin says:

    I was almost sympathetic towards Holly til she said she met with Hef and told him her feelings…..in front of a camera crew for her reality show.

  6. Scarlet Vixen says:

    I hate to admit it because I think she’s a complete and utter dumb*ass, but I really like the white one-shouldered dress Kendra is wearing.

  7. meg says:

    Is it just me or does Holly look like a female Kyle MacLachlan (second to last photo)? And the white hair is teerrrrible on anyone.

  8. lili says:

    all hookers

  9. guesty says:

    both kendra & especially holly’s spinoffs are more than a yawn. can’t believe they keep getting yet another season.

  10. anoneemouse says:

    “I’m very surprised,” Madison told Malkin. “I have a lot of different feelings on it. I don’t just feel one way.”

    Yes you do…it’s called jealous.

  11. Tess says:

    Holly always craved a centerfold, but Hef always nixed it because he didn’t think she quite cut it in the looks department.

    She knew where his head (and other parts) was at.

  12. Johnny Depp's Girl says:

    Holly, you are too young and pretty to be worried about that old fart.

    You will land yourself a rich man who will knock you up, guaranteed. Just make sure he’s relatively young. You want to enjoy that dong!

  13. brin says:

    @guesty…I agree…forget Seinfeld, Holly’s World is the real show about nothing.

  14. malachais says:

    Guesty,ita. Bridgett is hosting a pretty cool travel show on the travel channel, last I heard…so she is doing better than these gals.

  15. Leticia says:

    Kendra seems bored with Hank. I get the vibe that she now thinks that she could have done better than Hank. Don’t know why he married her.

  16. MNGIRL76 says:

    @malachais – I thought that got canceled awhile ago? Too lazy to look it up & don’t really care because after I heard what these girls had to do at the mansion totally changed my opinion of them. I’m so naive, I totally thought the show was for “show”! Didn’t really think he could get it up anymore. Disgusting!

  17. HEB says:

    The ONLY reason Hef is marrying Crystal is because his sons turned 18 so he sold the house next door which led to Kim suing him which led to the divorce. If Holly had waited another two years it would be her with the ring. Simple and fact.

    But I think she’s much better off.

  18. JustBe says:

    Meg@7: ITA, I couldn’t place why her face seemed familiar, she and Kyle must have been separated at birth.

    I think that Holly is hurting as she realizes that she was just one rung up from all of the other hos at the mansion. For a while, Hef led her to believe that she was extra special to him. But, as it turns out, he/it can’t really feel that way about any woman because he views us all as possible chattel for his harem.

  19. endoplasmic_ridiculum says:




  20. Rosanna says:

    I like Holly. However I think she had plans involving kids that Hef didn’t share with her. At some points her plans got more important than Hef. I wish her the best but don’t think that having plans on somebody qualifies as loving him. I just hope – for him – that Crystal doesn’t have plans but just takes life the way it comes.

  21. Westcoaster says:

    Why on earth would Holly want to have a child with a man old enough to be her grandfather? Unless she had twins why would she want to change two sets of diapers(the baby’s and Hugh’s)?

  22. LolaBella says:

    Poor Holly, she did EVERYTHING in her power to get her ‘Puffin’ to marry her, but now he’s got a younger version of her.

    This is just killing her.

  23. Confuzzle says:

    Girlfriends? Don’t you mean prostitutes?

  24. DaveJoe says:

    @lili: Couldn’t agree more. xD

  25. Lola7 says:

    Holly looks different for some reason. I just can’t put my finger on what it is…..

  26. Matt says:

    @ lili, THANK YOU.

  27. Jayna says:

    Holly hurt Hef when she left. She said she wanted to be with someone she could have babies with. She tried with him but the IVF didn’t work. I believe Holly was the love of his life but the baby thing for her was too big. I remember how hurt he was by her leaving him.

  28. KLO says:

    Being hurt by someone leaving you doesn’t necessarily mean you loved them, it might just be hurt pride.
    Both girls did good to leave him, I’m actually genuinely glad for them.
    and Holly has beautiful eyes, I just noticed :)

  29. eternalcanadian says:

    So Holly left Hugh because his sperm was dead? Does that mean 24 year-old Crystal absolutely does not want children or is she just gonna persuade Hugh to write out his kids and leave everything to her when he dies? :P

  30. CB Rawks says:

    She’s way better off. She’ll get over it soon enough and see it was definitely for the best.

  31. Dannii says:

    really dont get why people are so quick to call these women “Hos” but dont give the same scorn to hef. there seems to be an incredibly harsh mysogyny streak in culture where these women are really damned but the men who use them arnt given as much scorn, if any. for the record i dont like anything to do with playboy, hef or his girlfriends, and wouldnt blink if the mansion burned down.

  32. Lee says:

    Sorry…this is just plain creepy and disturbing on sooooo many levels.

  33. Ja says:

    @Danii: I also don’t understand how everyone slates these, yet no one questions Kim K., who wouldn’t be at all relevant if she didn’t fuck for all to view!

  34. Trippin says:

    It cracks me up when they talk so serious about Hef “falling in love”. It’s so twisted. His sperm is dead? And that should surprise us why?

  35. Jamie says:

    He’s ridiculous.

  36. Anon73 says:

    I never believe or bought that Holly “loved” Hef, I think she was always calculating for his money. For her a”marriage” with Hef would put her in a different financial stratosphere altogether. She is jealous that this other women played her cards better.

    While I no longer like Kendra, at least she was more upfront about it being a business arrangement with Hef during the “Girls Next Door” seasons. She never pretended she was “so in love” when she was not. It worked for her at the time, the whole situation and she made no bones about it.

    For Kendra today and why I currently dislike her ” she went from being seemingly sincere and straightforward to dishonest with all her PR spinning and it does not become her. She has become Holly-ized. ;-)