Holly Madison upset that Crystal Harris scored an engagement from Hef

48393, LOS ANGELES, CALIFORNIA - Thursday December 9 2010. Hugh Hefner with his girlfriend Crystal Harris and his son Cooper Hefner leaving Katsuya in Hollywood. The Playboy millionaire reportedly stunned staff by taking his own food - a baked potato and pork chops - to the restaurant! Photograph: Greg Tidwell, PacificCoastNews.com
Back before Hugh Hefner hooked up with his latest 24 year-old coed main girlfriend (and those teen ex-felon twins that predictably bailed) he was with very slightly more age appropriate Holly Madison, who was 28 at the time of their breakup two years ago. (The other two girlfriends back then, Kendra and Bridget, went by the wayside too of course.) Holly later admitted that she was trying to get pregnant with Hef’s baby before she broke up with him, and that she had funded her own IVF treatments. Later Holly called Hef’s new girlfriends copycats, basically, and said she was worried that they would take advantage of him at a vulnerable time. As if her motives were pure.

It’s clear that Holly wanted more from Hef than just head cheerleader status, and that she left when she figured out he wasn’t going to propose to her. It’s not surprising to hear that Holly is super pissed that Hef got engaged to his latest piece, 24 year-old Crystal Harris, when she wasn’t able to score that ring with a lot of cajoling and fertility treatments.

Hef’s ex — longtime galpal Holly Madison of “Girls Next Door” TV show fame — is said to be very upset about the engagement announcement. She long tried to snare a proposal from Hefner herself.

“She can’t believe Crystal was able to get Hef to agree to something she had tried for so long,” said a source close to Hefner.

Even after Madison’s fling with magician Criss Angel — supposedly done to make Hefner jealous — and Hefner’s plea for her to come back to him, he still never proposed marriage or gave her a ring.

[From The Chicago Sun Times, Bill Zwecker's column]

Does that mean if Hef proposed to Holly she would have come running back to him? It’s obvious that she wanted more financial security from the geezer than just free rent and an allowance.

The article also claims that Holly might not have much to worry about and that Hef may never marry Harris at all. Zwecker reports that “sources close to Hef tell me they doubt there will be a wedding,” but if there is the source says if the wedding does happen “‘That prenup will be tighter than Cher’s most recent facelift.’” You know an old dude said that. It’s rare that anyone less than two generations older than Harris would use Cher as a cultural reference.

Will it be worth it to Harry to marry a guy her great grandfather’s age in order to get a predetermined payout after four years? Probably. It’s not like she had a career or much education to speak of before she hooked up with Hef. Harris is ambitious, though. People reports that she’s starting a singing career and that she has a line of makeup coming out.

playboy playmate 030509

48393, LOS ANGELES, CALIFORNIA - Thursday December 9 2010. Hugh Hefner with his girlfriend Crystal Harris and his son Cooper Hefner leaving Katsuya in Hollywood. The Playboy millionaire reportedly stunned staff by taking his own food - a baked potato and pork chops - to the restaurant! Photograph: Greg Tidwell, PacificCoastNews.com

HOLLYWOOD - APRIL 26: Hugh Hefner and Crystal Harris arrive at the world premiere of Paramount Pictures and Marvel Entertainment's 'Iron Man 2 held at El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Kevin Winter/Getty Images)

48537, LOS ANGELES, CALIFORNIA - Monday December 14, 2010. Crystal Harris, Hugh Hefner's girlfriend, seen attending the H.Wood.Beauty launch party at the Tea Room in Hollywood. Photograph:  Josephine Santos, PacificCoastNews.com

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72 Responses to “Holly Madison upset that Crystal Harris scored an engagement from Hef”

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  1. guesty says:

    holly seemed to ‘genuinely love’ hef. gnd was a show that had that certain quality to it that made you want to watch…kind of a mixture of ew & aw.

  2. teehee says:

    Well welcome to the club, kiddo— no amount of effort or manipulation can ever ‘make’ someone want to marry you.
    He likes you or he dont, he wants to marry or he dont.
    A harsh truth everyone blinded by–err, love?– has to learn although its been spoken for eons.

  3. Jen says:

    I remember reading an article not long ago where it stated that he was still supporting his ex-wife and that he didn’t want to go through all of that again. I think the Hef and Harris will stay engaged forever, no wedding.

  4. brin says:

    Oh Hef, you old cad, you!

  5. dre says:

    Yuk! Thats all I can say!! Just YUK!

  6. ladycj says:

    I think she looks a lot older then 24

  7. Jennifer says:

    Honestly, the first thought that entered my mind when I found out he proposed was, “Is he sick?” Not sick, like, he’s an 84-year old man dating a woman 60 years his junior, but sick, lick, actually sick. Is his health on a downward path?

    Then it was, “Ohhhhh, Holly’s gonna’ be pissssssed.”


  8. Obvious says:

    poor Holly. I think she really loved(s) him. Crystal i jut kind of meh. and i HATED those twins.

  9. Mari says:

    @ ladycj- exactly what I was thinking. No way she is 24. No way.

  10. Lori says:

    Wow, Harris looks a bit rough — older than Holly, even.

  11. peanut says:

    That is one of the oldest looking 24 year olds Ive ever seen.

  12. LisaMarie says:

    She may be younger than Holly but in some of those pics she looks a good 10 years older than her. The last picture looks the best – the one with the least amount of makeup.

    EDIT: lol, glad I’m not the only one who thinks she looks a bit old

  13. meg says:

    Why do these chicks making bank wear the crappiest extensions?

  14. Ferguson. says:

    Im not gonna say Holly loved(s) him, but she cares about him a lot, or not maybe that much… but more than Crystal for sure.


  15. teehee says:

    And another thought– just how much variety does one expect to find among the “blonde playboy bunnies that hef likes”, anyway?? All guys have a type, but this is a marketing niche in addition to that. All of the girls look the same. Nobody is copying Holly, any more than she is copying all the other Bunnies, too.

  16. lili says:

    she is not upset about the man,
    she is upset about losing the deal and face
    both are trashy, and he is no price in any way

  17. dread pirate cuervo says:

    Is it wrong that I’m upset for Holly? I think Hef maybe proposed to whatsherface to piss off Holly. Maybe for ratings?

  18. byrdie says:

    Ummm….she looks much older then 24!

  19. Stronzilla says:

    This is so abnormal on so many levels its difficult to know where to start. But on no planet would a normal 24 year old woman want to be with a man 60 years her senior unless she has serious father/grandfather issues or a cash flow problem. She may think she’s going to be ‘Pampered’ but she’ll end up changing his ‘Depends’.

  20. Whatever says:

    Ew, he makes my skin crawl. There’s no way these women want a man the age of their GREAT grandfather for love. It’s all about the $$$ and they are willing to dig for the gold in his wrinkled ass cracks. Revolting.

  21. Po says:

    Wow, where do you have to be at in your life to pimp yourself out to a 100 year old man.

  22. Jessica says:

    She reminds me of Sandra Bullock in the picture where she is wearing that yellow dress.

  23. launicaangelina says:

    once holly, kendra & bridgette left, i did not watch the show so i never paid much attention to the the new girls and what they looked like. this is really the first time i have taken a good look at crystal. she is pretty but she can’t be 24! would guess 31-32 and i usually guess younger when trying to figure out a person’s age.

  24. OfficialBitch says:

    Harris looks like a TRANNY. Sorry.

  25. juicyjackie says:

    i liked Holly, but she was very pushy about marriage etc

    You know what they say, when you are in love age aint nothing but a number. I also think he a fascinating man, rich or poor, young or old I would love to have a long conversation with him. He is very intelligent and charming.

    I do agree though there will be no wedding

  26. SRM says:

    I would love to see pre-plastic surgery pics. I love a good before and after.

  27. melinda says:

    Well Hef was still married when he was with Holly. Then, if I’m not mistaken his wife filed for divorce from him while he was dating Crystal. I think this is a matter of his “light being on” more than anything. I think this is best for Holly. She really wanted kids and his sperm was too old to do the trick. ;)

  28. Relli says:

    @Tee Hee your first post is sooooo right on! I have a friend who is always chasing guys to convince them to date her and I am always telling her to stand down, you cannot convince someone to like you. Either they do or they don’t. period.

    I know i have mentioned it before but seriously read Bunny Tales. Holly is not that innocent. She maneuvered other girls out of the house to keep herself front and center. She was also willing to do “things” the other girls would not do (Jezebel had a post on it yesterday with an excerpt from Bunny Tales). She changed a lot about herself for him and was very strategic in her conquest of Hef, in the end she lost out because you cannot control other people or make them love you. I am sure that she is more upset about losing the face and deal, as mentioned above, then losing him.

    Also this new girl Crystal looks like a younger version of his ex Kimberly.

  29. Eleonor says:

    @Relly: all the girls who want Hef, are all gold digger.
    Holly worked hard to achieve the status of “Hefnumberonegirl” seven years in the Playboy mansion it’s much more than the other bunnies, she sort of diserved that ring, but I think she’s lost any chance for the baby thing. I have the idea Hef doesn’t want children anymore, maybe because he just has children and doesn’t want to complicate their lives after his death.

  30. amanda says:

    he really doesn’t have that much money and he is old and ugly to boot. Not mention a perv…

  31. Johnny Depp's Girl says:

    ewwwwwwww and noooooooooo

  32. clorismetchum says:

    whores. all of them. there ain’t enough money in the world to make me give that shriveled little turtle a piece of the cooter!

  33. skibunny says:

    Having sex with him is only a step away from necrophilia. Disgusting!

  34. Rita says:

    I think there is such a thing as true love with an older man. After all, look at Anna Nichole Smith….what a trooper.

  35. Fishlips says:

    @ ladycj(#6)
    I was thinking the same. I’m 30 years old, and she looks way older than me.

  36. Relli says:

    @ Eleanor. I totally agree any woman willing to do that with an old man has other motives.

    the author of the book i referenced is/was an educated woman , with a law degree from pepperdine. I read her book because i was curious as to why someone like her would take up with Hef and Playboy. She is a TERRIBLE writer, and her tone goes back an forth between being a scorned ex and a grateful for the experience girl. But it answers a lot of questions on how they live and the whole arrangement with Hef. Most of it is interesting some of it is a little weird, like how he likes to keep their rooms like little girl rooms (pink and white) and how possessive he is of them, like making them feel guilty for wanting to visit their families outside of the mansion. It is definitely not as sexy as it seems.

  37. The Truth Fairy says:

    “She can’t believe Crystal was able to get Hef to agree to something she had tried for so long,” said a source close to Hefner.

    This is what some girls don’t get about marriage … it’s not about getting the guy to agree to it. They either want to do it or they don’t.

  38. normades says:

    24? More like 34.

  39. TeeTee says:

    WAIT!! Holly tried to get pregnant, even though Hef said on the show “he did not want anymore kids?”

    she took infertility treatments?? wow!

    the first thing I thought about about was “ruh roh” Holly.

    trying to secure 18 yrs of support and she can stock up on all the pink goodies and hello kitty shit in the world. LOL!

    glad they are not using my woo-hah on old Hef! YUCK!

  40. Rosanna says:

    Poor Hef! I mean, obviously Crystal knew how to play her cards well – I think Holly was way too whiney and with a definite agenda in terms of babies and marriage. My sense is that Crystal didn’t want to get married or have kids (she’s young!) so she didn’t push for anything other than some cash and various toys and Hef, who after all still needs to feel free, decided to propose.
    I don’t think less of him because of his weird sexual style. I do think less of him because he wants his woman not to have a life and be in awe of him (he said so in many interviews!). Of course either the woman is very young or she’s not going to be ok with that kind of macho cr@p!

  41. Anti-icon says:

    This sickens. Hugh Hefner at least had some years to “rethink” marriage……and this is what he came up with? Just in time to stay relevant before he croaks? Apparently. No class, Hef.

  42. the original bellaluna says:

    Called it! I knew Holly’d be pissed.

  43. Trish says:

    December 28th, 2010 at 1:36 pm
    Having sex with him is only a step away from necrophilia. Disgusting!

    Now I don’t care who you are, THAT’S FUNNY!!!

  44. C-Love says:

    Umm.. Crystal looks like a dude from the neck up. And an OLD dude at that! (Well, older than 24 anyway). Seriously unfortunate extensions, too. Step up your game, Crystal! Maybe then you could land a rich guy your dad’s age, as opposed to your grandfather’s.

  45. wunderkindt says:

    Old Hef is on so many meds, he probably doesnt even know if he’s even met Crystal yet, let alone gotten ‘engaged’ to her!

  46. Jayna says:

    I call bull on this story. Holly has said she left Hef because they were trying for a baby and he couldn’t get her pregnant and that it was a deal breaker for her. But that she knows she hurt him leaving him but that she really wants to get pregnant some day and needed to move on.

  47. Kristin says:

    This story makes me sad. I really, truly believe that Holly loved him. She purchased him those types of gifts that are meant for the long term (It was a pet, I think it was the peacocks). Gold diggers just look pretty and jump into pap’s photos. I feel really bad for Holly :(

  48. JoJo says:

    Oh well, Holly still has Vegas! Yay! Who in their right mind wouldnt want to reside in that classy town?

    I saw a few episodes where Holly was a tool to the staff at the mansion. I am sure it was Hef’s right hand peeps that talked him out of marrying her. He probably proposed to this Crystal chick just to keep her around and maybe she will get that cute playmate house out of the deal or something. you go girl.

  49. Louise says:

    I think Holly really loved Hef. Well, love may be too strong of a word but she cared about him deeply either as a friend or father figure. Crystal just wants money and celebrity. I only watched a couple of episodes of Crystal’s season of GND. I just hated the new girlfriends.

  50. Marie says:

    In the top pic all I see is Dina Lohan.

  51. LBees says:

    I liked Holly, haven’t read Bunny Tales but will check it out. New girl isn’t as pretty. It’s all a little weird, sure, and definitely not to my taste.

    But what do I know? Right, wrong, these are the choices they make. Who am I to judge!

  52. kim says:

    Crystal has a hard edge to her face…looks soooo much older than 24….but anyway you slice it….ewwww

  53. mrsodie2 says:

    Hef was married when he was with Holly. He had a deal with Kimberly Conrad to stay married until their kid was a certain age. Holly wanted to be queen of the realm. I think she wanted the power over the other girls more than anything. And the lifestyle, natch. I figured she felt she’d earned it, putting up with old man smell and watching those old movies over and over and putting up with him taking his own food to restaurants. But she got fame out of the deal, so she didn’t make out too bad.

  54. Jennifersandiego says:

    Well, I sure feel so sorry for Holly. Yes, she is calculating, but she did devote 7 years to Hefner. And she went through the painful fertility treatments.

    I don’t believe for a second Harris is better than Hefner. She must druged him to propose. She is now the only woman with him. He is under her control. What a cold blooded bitch, Harris.

    Wedding will be soon. It seems that Hefnter is all in her hands now.

  55. Jenny says:

    Holly was prettier, and truely loved him hes a loser and just trying to console himself. He may seem like a winner to masterbaters who idolize jerks like him Howard Stern…but even Hef wishes he could have a monagamous true love but his perversion has always gotten in the way, inside hes hollow.

    Ive seen nude pictures of Marilyn Monroe.. even though she was the first cover girl for his magazine… in this day and age I know Hef would actually say her boobs are too small. Pretty hard to fathom, but its the truth. Not even Marilyn could live up to todays false standards.

    Plus he has GOt to have herpes.

  56. Heather says:

    I’m 26, no way is that girl 24.

  57. sassy says:

    Ummm…Has someone told Hef he’s engaged?

  58. truthzbetta says:

    These comments are cracking me up, esp the necrophilia one.

    How can I read Bunny Tales or a summary for free so I can get the dirt, but not financially support this dirty old coot and his plastic gold diggers?

  59. the_porscha says:

    @Jayna: That was Holly’s public statement, but I believe they split because Holly wanted a baby (badly) and Hef has stated repeatedly that he doesn’t want more children. At the end of the day, it was a storm they couldn’t weather. I think he proposed to Crystal because CH probably doesn’t care about having kids with him as long as she’s the one who gets a payout. Sorry, that’s cynical, but at this point, these women are just playing roulette with the man and hoping to God they’ll be the ones still standing when he keels.

  60. truthzbetta says:

    @ Jenny

    Good point, not even Marilyn Monroe who had plastic surgery on her nose, dyed platinum blonde hair, and loads of make up and false eyelashes could make the cut in Playboy today.

    Something’s messed up with a mag that requires surgery and fake everything to look like “the girl next door.”

  61. Eleonor says:

    Well I suppose things are worst because Hef is OLD. Old people usually repeat the worst part of themselves,maybe in his mind is everything “normal” as it used to be in his heydays, but the fact is that maybe he is not that conscious anymore, and even if he does something strange, or he wants to do, he can say “I’m Hugh Hefner!”

  62. Christina says:

    I’ve always liked Holly. She seemed the most honest about things. Like she really cared about him. I’ll always be a huge fan of Holly Madison. I named my dog after her lol. I wish hef would of married her instead.

  63. tj says:

    I gotta disagree with you, Jayna. Holly is working on a Burlesque project (I think called Peep Show) in Vegas now. She’s also chasing every rich man in town. So she probably is pissed. Funny cause none of the guys want Hef’s left overs.

  64. Veronica says:

    It’s obvious that Holly Madison was truly in love with Hef. She wanted children. Hef knew this. Crystal is safe. She obviously is not in love with him and is using him for his money, fame and for security. In return he get’s a pretty young girl to look and keep him entertained. Holly ultimately had to leave because she wanted a family and a husband and Hef was unwilling to bend. She is young & wanted a full on commitment that Hef was not willing to give her. Engagements can last years on end. I doubt they will make it to the alter, but if I were Holly..I’d feel majorly slighted, even betrayed.

  65. Missfit says:

    This chick looks just like Lindsey Lohan on the top pics…he might as well get with Lohan herself or maybe her sister, since he’s sick enough to get with some broad barely legal…stupid perverted sick fuck. I thought Holly was sincere, but, who knows. Some people are pathological liars and good at being very persuasive and convincing. :/

  66. Kim says:

    Wow!!!! does Crystal look WAY different after all the surgeries she has had. She looks like a different girl. I like her nose better kind of -but she looks a little alien after the surgeries.

    Holly wanted to work at Playboy etc and seemed more into her career than Hef whereas Crytsal is dumb as a box of nails and has no career ambitions outside of marrying Hef for his money.

    Im sure he figures he doesnt have long to live and may as well get married but he wont leave her much – it will mostly be left to his family/ kids as it well should be.

  67. Kim says:

    24 my behind! More like 34!

  68. HEB says:

    Crystal’s make up line was supposed to be out 3 months ago…doubt it will ever make it. The music career probably won’t either, but thats the way Hef would prefer it anyway–so she still needs him.

    I don’t think they’ll ever get around to actually tying the knot either.

  69. Luckylilgem says:

    Holly is much prettier. Move on girl, there are more millionaires in your future.

  70. Renee Barone says:

    I think everyones initial thought was “man is Holly gonna be pissed!” I would be mad as hell if I had to sleep next to an Old man for seven long years and never get a ring! Holly was loyal to Hef, she was good to him and gave him 7 years of her youth, which we ALL know she was there for financial stability. I mean EVERYONE wants that, to be financially stable and set for life and now that Hef has given some chick a ring Im sure Holly is pisssssed!
    Hugh Heffner is NOT a dumb man, he knows what hes doing and theres no way that any woman would be able to take advantage of him anyway. His daughter is the one in control of Playboy and Im sure that his daughter makes damn well sure that her father isnt being taken for a ride. IM sure that Hef knows that Crystal doesnt want him for His hot Body or is turned on by him. He MUST know that shes in this for security purposes. Its a win win situation for the BOTH of them, He gets to sleep next to a blonde bombshell and she gets to cash in when he croaks! Even thogh there will be a Pre-nup Im sure she will get a little sumthin sumthin out of the deal. Hes 84 and wonr be around much longer and after he passes she will still be a young hot thing and can find true love with someone her own age and make babies. Its good for the both of them!

  71. ew says:

    Crystal has such a big head.

  72. Dabe says:

    I think the best for hef was Holly she was perfect and she loved him not his money or anything like that she wanted a child from him cuz thats what a lot of women in love want with the man that they loved, i hate crystal she just a ho, and those twins are just so stupid Girls next door with that new cast is awfull!!! i want holly briget and kendra back!!!!!!