Posted in: Famous Relationships

Hugh Hefner Engaged To Crystal Harris Again

hugh hefner and crystal harris

Hugh Hefner and Crystal Harris are engaged… again.

Harris famously called off their first engagement in 2011 but it looks like the Playboy and his former Playmate are ready to give love another chance. According to TMZ, Hefner and Harris are planning to get married at the Playboy Mansion on New Year’s Eve.

Harris, 26, called off her first engagement to Hefner, 86, just five days before their scheduled wedding.

At the time Harris said:

“For a while, I’d been having second thoughts about everything, so I haven’t really been at peace with myself lately … It was all just happening too fast for me. I just sat back and thought about it all … Is this what I wanted? And it wasn’t.”

Harris moved out of the Playboy Mansion after she called off the wedding but was soon back at Hef’s side. The couple rekindled their romance over the Summer and Harris officially moved back into the mansion in June.

Harris wrote on Twitter:

“Happy to be back home at the Playboy Mansion with @hughhefner and our puppy Charlie. I missed all the love and laughs … Yes Hugh Hefner and I are back together. Yes I am his #1 girl again. Yes we are happy. Hope that clears up any confusion! Xo.”

Hefner and Harris haven’t commented on their new engagement yet but an “inside source” said that the couple is planning a small wedding with close friends and family on New Year’s Eve.

Harris will become Hefner’s third wife if everything goes as planned and she doesn’t get cold feet again. This will be the first marriage for Harris, who was the Playboy Playmate of the Month in December 2009.

Are you happy that Hugh Hefner and Crystal Harris are engaged again.

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159 Responses to “Hugh Hefner Engaged To Crystal Harris Again”

  1. Barbara Ransom

    So basically, since she was probably "Black Balled" from her hob knobbing group of socialites she's back because she doesn't have enough belief in herself to go get a college education and have a career not based on her looks or who she's doing and Cap'n Crusty probably upped her allowance. Just thinking about him being "romantic" with someone makes me itch all over like scabies EWWWW!

  2. Anonymous

    Does he really thinks this woman loves him, he needs to go sit his old azz down somewhere and stop acting like a crazy old pervert!

  3. Ann Denise-Stowe Fishback

    I totally agree with you vee..I mean come on now, a 50 year age difference, I am sure they have nothing in common, except her spending his money………hahahah.

  4. Sharon Bennett

    This woman made a fool out of him in public..The reason she come back is because she can't cash in some big money on a book..and she is so use to living a good lifestyle..

  5. Kristy Ann

    I'm sorry no amount of money would lead me down the aisle with a man that is as old as my grandparents or even great parents age! Really ladies, you get turned on and love him enough to have sex with him and not want to run out of the room!

  6. Joe Clark

    So what? He's been engaged (and married) so many times, it's a wonder he knows who his fiancee de jour is. Does Christie Hefner, who "inherited" the Playboy empire have any opinion? Not that it matters to me, either, but when Hefner divorced her mom, was it because of what Mom did or because Hefner was trying to live up to the reputation of a playboy?

  7. Rodrigo Juan Vargas

    Really? Listen to ALL the haters on here! Hugh Hefner The "Hef" has been having the most beuatiful women in the world spoon fed to him for 60 years now! Why would anyone want to chastise <<< Pun >>> him for that!

  8. John Beck

    As Tina Turner signs, "what's love got to do with it"?
    He's getting what he needs and she's getting what she wants.

  9. Diane Humpal

    Oh…and he's old enough to be her GREAT Grandpa! 60 yrs. difference in age.

  10. Maureen Doyle Odonnell

    I wonder how many millions Hefner gave her to help him save a little face. I was going to say get his dignity back but he did not have any to begin with. They are giving "love another chance" How about business deal.

  11. Mike Gecan

    Past sick but both are getting what they want. Hef–probably his last shot at sleeping with a young woman, Her–$$$.
    Can you imagine how much dope and cash it must take to screw that crusty, moldy, wrinkled, tired old coot?

  12. John H Cranmer Jr

    sounds like YOU are a little envious….you can NEVER truely wear another man's shoes……HATER

  13. Anonymous

    Hugh Hefner needs to be 86'd from this marriage. Of course, she's pretty and probably makes a nice play thing.

  14. John H Cranmer Jr

    HEF doesnt have to LIVE UP to anything-he IS "Playboy"' personified,,,Sounds like YOU "need" to live up to SOMETHING but havent figured out what it is

  15. Jim Schmidt

    With his age of 86, she probably won't have to be married to him very long. He probably doesn't have more than a year ot two to live. She probably gets paid a bonus for every year that she stays married to him, kind of like James Brolin gets for staying married to Barbara Streisand.

  16. Barbara Ransom

    Not to mention his never ending supply of Viagra! Makes the Gold Diggers actually have to put out. lmao

  17. John H Cranmer Jr

    and OBVIOUSLY they both like SEX…..sounds like WOMEN are HATING…..SORRY, I am not Prince Charming but when I look at most of the women my age (47) they do NOTHING for me…out of shape/not even near as ACTIVE as me, tired all of the time/diminished libido…I'd MUCH rather have an energetic full of energy companion so that means YOUNGER…You go Hef !!!

  18. Kadie Burns

    I think you're right. She feels like it's her only option now.

  19. John H Cranmer Jr

    sounds like WOMEN are HATING…..SORRY, I am not Prince Charming but when I look at most of the women my age (47) they do NOTHING for me…out of shape/not even near as ACTIVE as me, tired all of the time/diminished libido…I'd MUCH rather have an energetic full of energy companion so that means YOUNGER…You go Hef!

  20. John H Cranmer Jr

    like WHY you are stuck behind that ugly/not as rich guy in your pic

  21. Ken Poitras

    for all you men that wonder what it would be like to live like the Hef, visit Pattaya Thailand and you will find out.

  22. John H Cranmer Jr

    he's a LEGEND….WHAT guy that you know that is that OLD is being serviced by a HOTTIE like her ??? You are just HATIN'

  23. Anonymous

    I's tough to live a lavish life style in a mansion and then suddenly move out into a poorer life style. She can fake it for a few more years and financially benefit immensely in the years to come.

  24. John K Gavin


  25. Harvey Lain

    Here we go again! This is pathetic, how old is Hefner now? 100 or so? This antrique couldn't get it up with Viagra and a splint. Time for him to just go away.

  26. Anonymous

    Every time Hugh gets a new girlfriend or gets engaged, Viagra stock must go through the roof becauese a lot of old farts think, "if Hugh can do it, I can do it too!"


    Beyond disgusting!

    I wonder what price these tramps put on their dignity, pride, and self respect to allow an old disgusting fart like Hugh touch them, feel them up, and eventually sock it to them. That girl's parents must have taught her to just go after the mighty dollar and materialistic things no matter how the little virtue she has gets sacrificed.


  27. Harvey Lain

    And I never did figure out why, he has always been weird looking as hell. Must be hung like a horse or have a tongue longer then Gene Simmons, or both.

  28. Deanna Lunn

    she wants the money and stardom that's all! she realized its hard out there without money! so she went back! point blank!

  29. Ellie Burns

    Hmm…guess older DOESN'T always mean wiser. Hope it works. Not shocked if it doesn't. SMH.

  30. Anonymous

    Comeon vee105105 stop being jealous. I live in the Philippines and have friends who are world war 2 veterans, same age as the sage of playboy mansion, living at times with 2 20 year old girls.The fact that it takes someone as rich as Hefner to pull of something like this, is evidence of the 'bone dry sex deprived' culture of the ordinary middle class American male.

  31. Marguerite Winningham

    John Beck I think they are both getting what they want . YAY for viagra I guess.

  32. Bob Lust

    are you kidding…he is sixty years older than she is….he is rich..I guess that is the attraction. Wired, I say Wierd.

  33. Tina Oakes Winstead

    Mutual Users=Little chance of a real relationship working. He wouldn't want her if she were over 30 and she wouldn't want him if he were poor. 60 year age difference is disgusting. Hugh is the Eternal Playboy who needs a young woman to make him still feel like THE MAN and she needs a rich sugar daddy Husband. It's a disgrace to the union of marriage. Why bother getting married? Really? Wonder if it was HER idea to get married to try to insure she gets money when he dies and he only agreed to it to keep her in his life and bed. YUCK YUCK YUCK!

  34. Arlene Labella

    I think this whole thing is one big joke, he could be her grandfather, she walked out on him once, she will eventually do it again. She is only interested in seeing how much and how fast she could spend his money. I guess he feels he don't have many more flings left in life so go to it as much as you can. It would not surprise me if she don't kill him. Does he honestly think this is love?

  35. La Nena J

    clearly she was a nobody after she called off the engagement last year and felt her life was over, so she decided to be with 'him" again so she can live at the mansion and well.. since he's already old as soon as he dies she wants all the money, seriously come on people honestly what 26 year old woman would be with a old man who is 86?
    he's a very, very rich man and that's what she wants. $$$ she prob loves him but who can tell really?

  36. Wanda Torruella

    What the hell does she see in this old man, $$$$$$! All he cares about is having a pretty girl to walk next to him, and that's all..Almost sure she doesn`t sleep with him. Who would?

  37. Tina Oakes Winstead

    Harvey Lain Hef doesn't need either. He has the ultimate turn on-big bucks and connections for the women to get into the magazine, modeling, tv, movies, and hanging with all the celebrities.

  38. Neo Leo Poe

    Money, wealth, and power…can even erase 60 years from someones body; and make them appear to be 26 once again. The situation between these two, is so transparent…that if he didn't have the 'money', that he has…she would not even have given him a second look!

  39. Angela Mittman Wisely

    What the hell is wrong with him… She is such a user and goldigger.

  40. Nick Ames

    let's see. make the math easy. minus 100 years, add back 14. 1912 plus 14 = 1926. Hubba-Hubba and 23 Skidoo! Movies had sound then, didn't they?

  41. Anonymous

    Harvey Lain I'd rather be with a horse or use my own tongue than let that old fart anywhere near me!

  42. Jon Donham

    ok.. so weve played this game long enough… exactly what is the dollar figure to let an old man enter your vag? she holds her breath and closes her eyes and in 2 minutes its over? or is it in her contract that she has to keep her eyes open barking hef hef hef. does she have throw up in her mouth?

  43. Anonymous

    She must have found out he was sick and is fixing to kick the bucket. That's just gross I don't care how much money the dude has he is 60 years older than her.

  44. Anonymous

    Why, Hef, Why? You don't need to be married to be happy. "Date 'em, don't mate 'em; do 'em, don't woo 'em." Hef, why don't you just find someone you don't like, and give THEM half your money and a free house; a divorce amounts to the same thing. I don't begrudge the fact that you're 86; god bless you. I don't even begrudge the fact that she's 26; hope you got plenty of Viagra handy. But WHY would you even think about marrying somebody that got "cold feet" the last time. Uh, uh. She had her shot and she blew it. Even now, tell her to sign a 20 year pre-nuptual agreement, we'll see how "loyal" she is with that over her head.

  45. Love Isalluneed

    Ha, that's a laugh. I am 42 and my friends and I have problems with the men my age and older having any energy at all. And before you make some disparaging comment about my looks/fitness level/personality (i know it is coming) these are usually YOUNGER women. Women my age are in our sexual prime( OUR sexual prime, you might not prefer women our age but that's another topic). Men, not so much. As for as being out of shape, not as active, that is entirely possible. You are likely meeting the wrong ones. Just like we clearly are meeting/married to couch potatoes. Point is, should not generalize.

  46. Love Isalluneed

    I should add I have no problem with CH/HH getting married and I don't care about intergenerational dating. Whatever works for people.

  47. Mark Mcconnell

    Wow, what a messed up world we live in! I've never met a 26 year old women that would consider having an intimate relationship with someones great grandpa! It's sad what money can do to people!

  48. Herbert Caplan

    This is a problem in arithmetic. How many times does 86 go into 25? Looks like First Obama and now Harris will be over- taxing him.

  49. Anonymous

    She is looking for a lifetime retirement, after he kicks the bucket.

  50. Margaret O Kyttle

    I really don"t see what these young girls see in this this sleazy Old Fart. Money or a chance at fame, I couldn"t stand for this old man to touch me.YUCK!

  51. Anonymous

    He is one man that should be scared to die. he has exploited, used, and molested so many weak and vulnerable women–for sex, money, and fame. From reading the bible, I do not believe that God is pleased with those that are in sexual sin. How can he live with himself? His soul must be rotted out because of his lack of virtue, and good moral , and virtue. this man has lived a life of lust, and not being genuinely caring of his girls at the mansion, because he is so dishonest–and I believe manipulative. A daddy pimp for them. The girls are so nieve, shallow. And they all love money.

  52. Mark Perry

    She didn't get her own reality show and everyone forgot about her, so that's why she is back.

  53. Amber Nelson

    First of all to the poster Joe Clark this would only be Hers third wife which in today's world is not as you put it "so many". What shocks me (even though it shouldn't be a shock) is how affected some of you seem to be by this. Yes it is a vast age difference but it is between two legally aged consenting adults. She is 26 not 16 and knows what she is getting herself into. How can all of you be so sure its not love or a very strong companionship that draws her to him? So you process some skill that allows you to seem into this woman's heart and mind. The last I had heard Her has always had ironclad prenups so while she will most definitely get to experienc the good life while she's married to him all that will go of the marriage goes.

  54. Amber Nelson

    First of all to the poster Joe Clark this would only be Hers third wife which in today's world is not as you put it "so many". What shocks me (even though it shouldn't be a shock) is how affected some of you seem to be by this. Yes it is a vast age difference but it is between two legally aged consenting adults. She is 26 not 16 and knows what she is getting herself into. How can all of you be so sure its not love or a very strong companionship that draws her to him? So you process some skill that allows you to seem into this woman's heart and mind. The last I had heard Her has always had ironclad prenups so while she will most definitely get to experienc the good life while she's married to him all that will go of the marriage goes.

  55. Amber Nelson

    Sorry about the typos the her was supposed to be Hef and process is possess and so I was writing that from my cell phone and it has that darn auto correct typing which just auto-screws everything up for you instead of auto correcting…

  56. Anonymous

    why would he care if they love him? he is 86 yrs old and still banging the hottest 20 something year olds on the planet. ofcourse they are there mostly for the money(although I bet he's an interesting dude to hang with), but so what. Every man on earth still wants to be him, and always has. Hef rules!

  57. Greg Winski

    If Hef didn't have a dime to his name, a mansion and was wealthy, this broad wouldn't give him a second look. She's a fking gold digger and I hope they have a pre-nup. WTF is she going to do when Hef has to go Ci-Alice every night LMAO.

  58. Kimberly Mullen Nugent

    He is 86 years old! How much longer do you think he has? I hardly doubt she is going to get his entire empire when he goes. It sure would be interesting if she does and will clear up why she married for the first time with someone so darn old. Love for her is full of doubts as the article still states. That is not a positive thing to have when you walk down the isle.

  59. Ace Boogie

    I don't care what nobody says Hef is a mack he keeps stallions in his stable at all times, every body well cared of living good eating good and just plain living the life what more could you want ask for. and people wonder why there broke now always trying to worry about the jones when you should be worried about your own priorities.

  60. Anonymous

    Hugh has been taking advantage of these women for years. They are beautiful women with very little talent. The sex must be torture for these women.

  61. Lisa Williams Sears

    well Hef- I sure hope this 10th marriage of yours, brings you "peace". although I am not too sure peace is what you really like. you seem to thrive on the revolving door…..maybe the 10th time is a charm! good luck!

  62. Bernardino R. Villorente Jr.

    Crystal Harris should be jailed for having sex with a minor since Hugh Hefner is in his second childhood!

  63. Jessica Bradley

    What I don't get is why he absolutely refused to marry Holly Madison, who seemed to genuinely love him and yet he is willing to marry this skank who made such a fool out of him. Men are idiots!

  64. Delia Oriol Palmer

    gold digger, crystal you keep digging and digging hugh hefner money, why you don't know how to find a decent job?, just digging to this old man money?, you are so ugly, take off that air brushing makeup in your face or any make up, I can't emagine how look scary are you and you are so look cheapy woman, I'm just telling the truth, ha, ha, lol.

  65. Theresa Ann Carlson

    Actually she went to SDSU and graduated with a psychology degree. So she has a college education!

  66. Renee Brooks Tatum

    I was going to say the same thing that vee105105 said. Hugh is older than me and I am a grandparent and great grandparent. I would not even consider being a cougar. My grandson told me grandma I want to see you with a boyfriend. I told him what would I do with him? Really now, and this is the truth for me after a certain age, you just don't have the energy it takes to date and go through all the La, de, the. All those seniors who want what Heft has, God Bless you!

  67. Anonymous

    who said money cannot buy aimost all things she got "broke" she got back to where she can get it she will now "clean" HH.
    up she must realy love good life. When no network buys her story she had to comeback Goodluck Hef.

  68. Anonymous

    she really loves him…i swear this time…………………………………………..

  69. Melissa Fugh Leyes

    I think making fun of Hugh is rude! One day men you may be in his shoes! When you age it is your body that ages but your mind is still the same. I truly think Holly was in love with Hugh. I think Holly is right when she said Crystal just want's babies and who better to have them with but Hugh….They would never have to worry about money and neither would she. I feel sorry for Hugh, everybody needs someone, and he probably is in love with her and wants to marry her for the right reasons. It's her reasons I do not trust!

  70. Farrah Teague

    Crystal Harris is way too young for this man. He's old enough to be her grandfather, or even great-grandfather for heaven's sake!

  71. Victoria Warnar

    YIKES! I am sure she is going to want to Hang Around… with this GEESER and his BIG FART Brother..

  72. Brian Sweet

    Freddy Krueger and the GOLDDIGGER in theaters next summer! If he is dumb enough to marry that he deserves to be screwed in more ways than one I might add!

  73. Jamie Wilson

    Hugh Hefner should not take her back. She had her chance and she embarrassed him in front of millions when she called off the wedding last year. He has lots of beautiful women wanting to be with him so he must really have feelings for Harris. In my opinion, she is there for the money. It would be funny if he made her sign a prenup agreement and she only got a couple million if they split or if he died. Lol.

  74. Anonymous

    There's not enough money on the planet for me to let that man lay one of his disgusting paws on me.

  75. Anonymous

    I heard Hugh has taking to snorting viagra now (reliable source).

  76. Dianne E Lang

    I would like to see Hef and Lindsay Lohan. together. now THAT would be entertaining.

  77. Anonymous

    Better hurry up and marry him. He doesn't have much time left to walk the plant.

  78. Anonymous

    At 86 she's probably thinking, "Oh what the hell, he won't be around that long, so I will merry him and suffer for awhile." I admit, he will die with a smile on his face. Most people who hit that age would die alone, not this guy, giving the old stick until he can't know more. Go grandpa.

  79. Bill Bienapfl

    C'mon now Mark…she probably really in love with him, and even if he were just some old dude on a fixed income they would be together lol

  80. Cindy Lee

    She totally humiliated him on the Howard Stern show, not to mention running away the week before the wedding…what an old kook his is to think she wants him for who he is…she's a gold digga!!

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