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Holly Responds To Hef's Engagement!

| Filed under: Love LinePlayboyHolly Madison


Uh-oh! She's finally speaking out about this!

And it ain't good!

Hugh Hefner's former long-term girlfriend, Holly Madison, has heard the news that the Playboy honcho is marrying Crystal Harris, and she does NOT think that it's a particularly good idea!

She explains:

"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. I'm not jealous that he'd marry someone else. I just don't want it to be a girl who's using him to start her career. Basically, I think he could do better than Crystal."

She makes some inneresting points!

But one could definitely argue that this is just sour grapes, on her part!

What do U think?? Are Holly's concerns legit or is she, in fact, just jealous that he didn't put a ring on it??

[Images via WENN.]

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69 comments to “Holly Responds To Hef's Engagement!”

  1. 1

    That's awesome Holly's being real about it, even if she is a bit jealous.

  2. 2

    I think Holly's points are right on, but at the same time I would be a little pissed if i waited around for someone who "didn't want to get married again" and then find out he popped the question to a barely legal girl.

  3. 3

    Poor Holly.

  4. 4

    Maybe he'll ditch Chrystal for Kendra. Looks like Kendra (spoiled brat that she is) is ready to dump Hank and move back into the Playboy Mansion.

  5. 5

    I dont get Hef! He had Holly who waited around and wanted to settle down and he loved her and he wouldnt settle and no he is marrying a girl he barely knows!:s I'd be pissed if I was holly.

    And too right Crystal is trying to jump start her career-what happens to his other gfs the twins ?

  6. 6

    She is totally right, this bitch is using him… But then again they were all after his money and all using him to jump start their career, so what room does she have to talk. Who the hell was Holly Madison before Hugh Heffner.. This new bitch is just doing the same thing only with a bigger payoff.
    No chance he will find true love at his age unless he finds someone closer to his age. But Hugh Heffner is a child that never grew up.. he just built a larger sandbox than the rest of the kids… and all of the little girls want to come play in his box and leave when they've had their fun.. He lives in a false world and will die lonely and taken advantage of, that was clear decades ago.

  7. 7

    i dunno why but i always thought holly legitimately loved hef…i've always liked her. :)

  8. 8

    WTF would be in love with the crept keeper. we all know they all dating him for the money and to start off there career the only real loyal women he ever had was his first wife. to bad they are divorced now.

  9. 9


  10. Beccx says – reply to this



  11. 11

    i feel bad for her. she really wanted to marry hef and have a family with him. i agree with her, although she has put it in nicer terms, that crystal is a gold-digger. holly seemed really sweet, and im sure she will find someone special.

  12. 12

    Holly, your in a better place now that you have moved on. You have a beautiful son. Hold on to that thought.

  13. 13

    I feel she really loved him. you can just tell when you watch the show. and did you see that doll house she ordered for him, of his childhood home. and he recieved it after they broke up. i do think this new girl is using him. holly may have been with him just for the money and job at first, but i do think that she fell in love with him. screw this new chick. i hope holly finds the love of her life !!

  14. 14

    She is absolutely right. Everyone could see how much he loved Holly and he didn't marry her. Something is up with this girl. He should have married Holly…..she's the only one that actually loved HIM.

  15. 15

    Wow… damn i'm actually quite surprised how honest she was.. i mean yeah i'd be pissed if i was her but i'd also be concerned too.. It does seem fast specially when he said he wouldn't marry again.. never really liked Crystal or the other 2 idiot chicks.. but it's funny in her comments she's acting like it's someone who's going to live for along time to even get a chance to get divorced.. but i definitely give her props for honesty and not holding back xD

  16. 16

    Eeewwww. He's just….eeewwwww

  17. 17

    Totally jealous. She fears that Cristal will use Hef to start her career..that is hilarious. Holly did the same thing. Maybe Hef didn't feel the constant pressure from Cristal to make more of a commitment, like he did with Holly. She was constantly hounding him about marriage. And she doesn't want him to get hurt. LOL I guess her dumping him for Criss Angel didn't hurt Hef. whatever..She is so pissed that he didn't w ant to marry her.

  18. 18

    I totally agree with Holly. It's a $ issue. Marriage = commitment of 50% of your finances not just commitment and there is always the possibility of divorce. She is YOUNG. Hope Hef gets an iron-clad pre-nup where she gets nada when they divorce. Think she is really in love with him or his $ and fame and the lifestyle? I do think that Holly might have been okay with him having extra g/friends and never insisted that he marry her so maybe that's why he is engaged this time around? I am happy Hef is happy and in love, but you gotta think with your wallet not just your !@#$ lol.

  19. Jen83 says – reply to this


    I agree 100% with her…. I think she's gross and unhanding. She came in comparing herself to holly to everything… she's just a mere shadow… paranoid one @ that… I thought Hef was better than that.

  20. 20

    Re: Abbylynn – She doesn't have a son >.>

  21. 21

    anyone would be a little jealous if they were in holly's position but no holly is totally right, hefs jumping into things too quick

  22. 22

    Hefner has used women his whole life — he is a porn magnate. If he gets used in return (and of COURSE *any* woman in her 20s dating an octogenarian IS using him), sounds like just desserts.

  23. 23


  24. 24

    I reallly loved the girls of the playboy mansion and the show really made me think Holly genuinly loved Hef, and he has totally thrown it in her face.
    I'm sure she will be invited to the wedding but how hard to see.

    Love Holly's world and hope she finds a super amazing guy!

  25. 25

    Jealous? Yes. Genuinely concerned? Probably yes too. Holly really loved him, I feel bad for her.

  26. 26

    She does have some valid points but she is a jealous hater. She wouldn't have Peepshow if she wasn't famous for being one of Hef's whores.

  27. Megz3 says – reply to this


    I feel bad for Holly! When I heard the news the first person I thought of was Holly. She put like 8 years into their relationship and probably knew him better then anyone. It's to bad he didn't ask Holly to marry him cause I think in the end they made the best couple. I like Crystal but I think Holly's right…Crystal is to young and doesn't know the business!

  28. 28

    Theres quite a bit of dirt floating around about this Crystal character. The general consensus is that shes the typical trashy partying whore whos looking for a payday and Hef is just too senile to see it.

  29. 29

    HOLLY FTW!!!!!

    i think she's a bit jealous.. but who wouldnt be?????????????

    crystal looks just like a gold digger whore!

  30. KBGD says – reply to this


    Re: mattihilton – I'm thinking that he knew holly wasn't in it for the right reasons and that's basically it… he's not a stupid man.

  31. KBGD says – reply to this


    PS… don't feel bad for Holly. If she really loved him she wouldn't have moved to vegas. It's as simple as that. She wouldn't have jumped straight into another relationship. Just sour grapes!

  32. 32

    & Holly wasn't a golddigger that used him for fame? Btw it worked quiet well for Holly she is doing well for herself. Who else would want that old snake?

  33. 33

    Although I am not sure of why he and Holly broke up to begin with, but from this whole rush engagement and I do sense a little anomosity and hard feeling towards her still. I believe that he is putting the ring on to make Holly jealous as he knows that it is what she really wanted from him and I think he is still bitter that she left him and he is still inlove with her. I am sure he and Crystal will not last.

  34. 34

    Ii think Holly is a little jealous, but can you blame her, if she actually loved this old wrinkly man and i think she actually did, for more than his money, then of course shes jealous, but she has a point and i think shes absolutly correct in saying that Crystal girl just wants his money…hello she is 24 years old..saying she doesnt want kids…and wants to be married to a 84 year old man…and shes not famous for anything but that…yes she just wants his money and to make a name for herself off of it.

  35. 35

    I feel bad for Hollz, she paid her dues but never got the ring.

  36. 36

    Re: Abbylynn – Kendra has the son not holly

  37. 37

    I would be really mad if I was Holly. She wanted to settle down and he said he didn't want to and then got engaged right away? I don't care if you are Hugh Hefner or part of the general population. That is shady.

  38. 38

    Totally agree.. come on.. the girl is a golddigger… as if she can really be in love with Hef.. if he didnt have money would she be with him? These old guys just dont learn..

  39. @v@ says – reply to this


    That's got to sting for Holly. If she truly had these concerns, she maybe should have gone to Hef with them instead of the media. It's a bit of meow.

  40. 40

    Shes just saying what everyone else is thinking!

  41. 41

    This is the sad thing. I honestly believe Holly was 100% in love with him. Unfortunately, I guess he didn't feel that way towards her. Not everyone is after people fame and fortune. I think because she truly cares about him she is expressing her feelings. She maybe right. But Hef is going to do what he wants good or bad. He doesn't have many years ahead so I guess if it makes him happy so be it. Holly will find someone else. Not the same but she's a beautiful person. Was my fav on the show.

  42. 42

    Probably a little bit of both. Maybe Hef should listen to her, after all, she is someone that loves and cares for him.

  43. 43

    He's 84 years old… who cares if he "settles down" at this point? And Holly, it's okay to admit you're jealous, even if this girl isn't "good" for him.

  44. 44

    waa waa..why does everyone feel sooo bad for holly…believe me this narcissistic bitch will suceed in the one thing she has set out to do & marry rich…i hardly feel bad for her

  45. 45

    To be totally honest, I agree with Holly 100%. AND I think Holly genuinely loved him and I don't think Crystal does. I've met both of them and the vibe was real with Holly. Hef would have been better off marrying Holly. I don't think she would've used him. Crystal has openly said that she was trying to start some big projects. Ummm…and where would she get the money to start these projects??? Exactly…

  46. 46

    she is totally right, I bet she was after him for the same intentions but now she is not, and it is obvious that she will take all his moeny, poor guy he doesn't want to be alone and he is risking his money for girls that don't want him

  47. 47

    Re: Abbylynn – she doesn't have a son, are you talking about kendra?

  48. 48

    For those of you that say that Holly used him too to jump start her career. Not true. She was with Hef LONG BEFORE The Girls Next Door. That show, which HE suggested they do, is what started her career. Without that show, she would still be a nobody just like all his other ex-"girlfriends." None of them are doing shit.

  49. 49

    Im not 100% positive when Holly and Hef got together, but I am pretty sure it was a few years before The Girls Next Door. So i am not sure how much of the argument can be made about Holly using Hef to jumpstart her career. The Girls Next Door did, but if it wasnt for that more then half of the population wouldnt have known Hugh Heffner even had girlfriends (Im talking people who started watching or paying attention to this in the past 6 years or so), so she wouldnt have been known. But like I said, I am unsure about the start of the their relationship.

    As for her comment, I think she is right. Jealous and hurt, yes, but who wouldnt be. I mean anyone that watched the show knew their was real chemistry between Holly and Hef (that wasnt between Hef and Bridget or Hef and Kenda) and she genuinly seemed to want* to settle down and have a family with Hef. However towards the end I think she, as would anyone who belived in marriage not just being in relationship (because its not enough for osme people), as well as Kendra and Bridget began to date others. Im wondering if they actually all broke up earlier, continued the sow for publicity and all moved onto to new serious relationships because they had been with them while still filming. But who knows. I think overall, Holly's right, Crystal is a new character who we dont know much about. And what i have seen of her, she doesnt seem ready to be married.

  50. 50

    Holly's absolutely right about everything! Crystal is obviously a fake-as-hell gold-digger who is only with Hef for the $ and career prospects. If you look at every picture taken of Hef and Crystal, she is pushing herself forward and acts like she doesn't care about who she's with aat all–it's ALL about her. On the other hand, if you look at any of the pics taken while Hef was with Holly, Holly is usually gazing at Hef adoringly–I think she truly loved, and still DOES love, Hef for who he is as a person, the way it should be.

    I think it's tragic how Holly waited so long for him, but eventually had to give up because he flat-out told her he would never settle down…and then he goes and rushes into things with this new girl. I think he got lonely and realized he wanted a more permanent companion then he has had in the past…it's just a shame he didn't come to this realization when he was with Holly.

    I think Holly's right–I think Crystal will end up breaking his heart and robbing him blind. I also think Holly will be there to pick up the pieces b/c she's not going to find a deep, serious, loving relationship when she's still in love with Hef like she obviously still is.

    Make sure you have an ironclad prenup, Hef–especially since you've just bought Playboy back! It would be a real shame if Crystal gets a piece of the ownership instead of it going to your two sons!

  51. 51

    Can't fault the girl for being honest can we? I know Crystal & it is safe to say I agree with what Holly has said. She tried many different types of shows / media to get famous, and when all that failed she started sleeping with rich old men for money.. Hef just being the latest & a semi succesful attempt at people knowing her name - even if it is for being a paid whore, which technically is what she is.

    She has her boyfriend on the side (which she actually had before moving in to the mansion - and remains to give her, the loving she needs that she cant from an old man) and is waiting to get what her intentions originally were and then leave with a whole new, rich life.

    She is a nasty little girl who will stop at nothing to get money. She will screw over her best of friends and everyone who helped her on that way up the ladder (remember Crystal, that saying about watching who you step on, on your way up? ) and which she has proven to do to many girls already.

    The girl has constantly tried to be like Holly, hell she always wanted to be Holly, and has had multiple surgeries to try and make herself a natural beauty, which has just aged and aged her and she now looks a lot closer to Hefs age than she actually is.

    This girl is a disgusting pig who destroys lives - there is a bit of goss on various websites if you can find them :) A nice place to start would be the dirty for a few vague comments..

  52. 52

    who honestly gives a fuck who that corpse marries, that bitch is out for hef's money come on!! let me guess she is genuinely attracted to him….without $$$ that mother fucker aint shit

  53. 53

    Pot meet kettle. Everyone who dates or marries Heff is an opportunist to some degree. I am certain he had his legal team draft up an iron clad will that will protect his assets for his kids and family. Holly not the brightest crayon in the box but she knows this. She got more sympathy from the public when she took the high road and kept her mouth shut.

  54. 54

    I'd be pissy too if I was her…. she has every right to be.

  55. 55

    Holly says this new girlfriend is just using Hef and wants to get her name out there to build a "career"..that's calling the kettle black! Duhhhh!

  56. 56

    ha ha ha,JEALOUS bitch….. the new one is gonna take Hef's money like Anna Nicole Smith did,so other blondies are totally desperate and jealousssss

  57. 57

    Are some of you seriously that oblivious here? Granted anyone dating Hef is looking to jump start something but- before the show how often did you hear about Hef's other girlfriends? Oh that's right, you didn't. I mean you knew he had them, they might get a centerfold here and there and be entitled to more magazine and mansion wise but it wasn't at automatic catapult into fame.

  58. 58

    Please Holly is so fake. She is just so mad that Hef choose this other girl over her. Get over it, he didn't want you sweetie. And lets be real Crystal is by far the best looking girl I have seen on that show. And she seems really sweet. Stop being a hater Holly.

  59. 59

    NEWSFLASH Holly: There's no such thing as "settling down" with a man who's about to bite the big one! It's doubtful he'll even live another five years.

  60. 60

    Aren't all the playboy girls after money and fame, otherwise what would be the point? Holly sounds like a jealous cat to me. As for loving Hef for Hef, would she still have "loved" him if he pumped gas for a living. Can't see her being into a pervy 70-something if he didn't have to dimes to rub together. Holly has zero talent and she is right to be scared of someone stealing her crown. There are plenty of pretty girls waiting to take her place. If you've no skill or talent you're only going to get 15 mins and I think Holly knows her time is up. Next generic nobody step on up.

  61. 61

    that girl Crystal doesnt want to Marry Hef. What 24 yr old wants to marry a man that all he wants is to stay home, give him his medications,probably does dialysis from time to time, is sexually dysfunctional, and probably has uncontrollable bowel movements. What she wants is that $$$. There is not one person that thinks this marriage is based on LOVE. Holly was best but it is what it is.

  62. 62

    One more thing, why does anyone care if hef gets taken for a ride?! He's made a fortune out of being a misogynist. It'll be poetic justice that one of the 1000's of women he's exploited walks away with half his earnings. Serves him right for thinking any young women, of this type, would be into him for him. Like the saying goes, there's no fool like an old fool…..

  63. 63

    It's the same thing as these girls competing for Flava Flav's heart. If these men were sitting in nursing homes in wheel chairs, not one person would look twice at them. No 20 something year old girl in the prime of her life with everything going for her is going to settle down to marry an old man. Sorry, it's just not logical.

  64. 64


  65. 65

    Re: Jen83 – First of all Holly is NOTHING compared 2 Crystal. Crystal has an IQ of 138 and in interviews is a really really INTERESTING person. She has more to offer this world and HH. Plus she is SOOOOOOOOOOOOOOOOO much hotter in looks, Holly could not compete. They are totally separate leagues.

  66. 66

    Re: steffixo – What?? IQ doesn't mean you're more interesting or better than other people. If you think it does, so you must be VERY VERY VERY low under millions of people, like many of us!

  67. 67

    i agree with holly because holly knew him for 6 years and he barley met crystal 2 years ago wtf is that shitte, holly honestly loved him =], thats just wrong there

  68. uyeah says – reply to this


    Who is she to GUESS, cattily, that Crystal MIGHT be wrong? It's no longer any of her business. Doesn't she know Hef well enough to know if he can make a sane decision? It's a diss on Hef from her! What a stupid thing to say in public. I don't think Hef appreciates it. If Crystal has anything to say about it Holly won't be seen at the mansion anymore and rightly so.

  69. 69

    Holly is SO RIGHT. does NO ONE REMEMBER that Crystal Harris was a girlfriend of Hef's several years before the show, with Holly, when Hef famously had his 7 blondes- one for each day of the week? And he broke up with her and sent her out of the mansion?! And then the last season of the original girls next door, Crystal tried to come back and begged Hef to let her move in and be on the show. Holly was able to block the super obviously gold-digging Plastic that time, but unfortunately, she came clawing back for a third, and now it seems, final time. And for a 24-year old, she's pretty, but even I look younger than her! Holly is waaay more beautiful, and looks younger at 31 than Crystal at 24!! And I dont even think she's jealous. If you remember, SHE broke up with Hef, when they weren't able to get pregnant, after SEVERAL TRIES, NOT the other way around.