Gotta Watch: May-December romances
Crystal Harris has called off her wedding to Playboy founder Hugh Hefner
June 15th, 2011
11:06 AM ET

Gotta Watch: May-December romances

Perhaps Crystal Harris didn't want bridesmaids wearing bunny ears. Or perhaps she got tired of people suggesting her fiance was the "old" in "Something old, something new, something borrowed, something blue." Whatever the reason, it's official: Harris has called off her wedding to Playboy founder Hugh Hefner. Since much of the fascination about Hef and the Playboy Playmate centers around their 60-year age difference, today's Gotta Watch looks as some of our favorite May-December romances.

Harris makes "The RidicuList" - CNN's Anderson Cooper says he just doesn't get why Hefner's ex-fiancee would call off their big day.  He managed to put her on "The RidicuList" with references to dogs and hydrants, orthopedic shoes and penicillin.

'Til death do us part - What's the secret to a successful marriage?  Selflessly sharing the mic at a press junket? Polishing your spouse's star on the Hollywood Walk of Fame without being asked? Here, Ashton Kutcher and Demi Moore say it's as simple as a Post-It note.

Donald and Melania - Before Donald Trump flirted with the idea of running for president, he was flirting with now-wife Melania. Here, she tells HLN's Joy Behar that she initially didn't want to give Trump her number. No, it wasn't because he wanted to see her birth certificate.

Watch Anderson Cooper 360° weeknights 8pm ET. For the latest from AC360° click here.

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Filed under: Celebrity • Donald Trump • Showbiz • TV-Anderson Cooper 360
soundoff (82 Responses)
  1. banasy

    Can it, Casey!

    Anyone who would want to marry Hef in the first place is...well....

    Yuck. I'm off to shower, I feel icky dirty now....

    June 15, 2011 at 11:33 am | Report abuse |
    • Ed Sr

      May-December romance?.....................NAWWW........................how about 1920.......1986 romance! He was 66 when she was born.........................wow............what a retirement package.......better than a 401K................

      June 15, 2011 at 1:50 pm | Report abuse |
  2. Jazzzzzzzz

    Casey should can it already. So tired of this nut banasy.

    June 15, 2011 at 11:54 am | Report abuse |
  3. Riff*Raff

    I'm sure it was true love all the way. A 60 year age difference is beyond pushing the boundaries. Hef definitely has a "type". If you lined up all of his exes they could be related. His daughter is older than all of them as well. His lifestyle isn't exactly condusive to married life.

    Other than Demi/Ashton, the others referenced in the article are just chasing the $$$. Attracted to the Trumpster? Yeah, right.

    June 15, 2011 at 12:19 pm | Report abuse |
  4. Tom

    When it came to Hefner's lifestyle, I was always of the opinion that it was his life and certainly none of my business. At 85 years of age, if he can convince a girl easily young enough to be his granddaughter (or even great-granddaughter) to crawl into bed with him, then that's up to the both of them; not me. No matter how absurd I think the union might be, they're both old enough under the law to be making their own decisions. At 85, he won't be chasing bunnies much longer, no matter how much Viagra he can get his hands on.

    June 15, 2011 at 12:37 pm | Report abuse |
  5. Dudley

    I'm not mad at Hef.. Don't know why women are always acting like they really care about love. Women want love on their terms and usually the man isn't good enough. If I never find a girl to settle down with then I'm gonna buy expensive toys and put some girls through college. Not a bad plan B if you ask me. Plan A isn't looking that great right now. Women let all the jerks have their fun and look for a nice guy to play clean up duty.. No thanks. To each their own.. Go Hef!

    June 15, 2011 at 12:53 pm | Report abuse |
  6. Barry

    It’s hard to tell which one is more pathetic—Heffner or the gold-digger.

    June 15, 2011 at 12:57 pm | Report abuse |
  7. Jazzzzzzzz

    I'd do any her. He he.

    June 15, 2011 at 12:57 pm | Report abuse |
  8. Melinda

    $$$$$$$$ I love you Hef $$$$$$$$$$$$$$$$$ I love you Donald $$$$$$$$$$$$$$$$4
    gold digging women are pitiful

    June 15, 2011 at 1:13 pm | Report abuse |
  9. Amy

    She probably didn't like the Prenup

    June 15, 2011 at 1:23 pm | Report abuse |
  10. Don

    My bet is that Heff suddenly presented a prenuptual agreement that removed most of the financial incentive for the marriage. She suddenly decided she didn't love him any more.

    June 15, 2011 at 1:27 pm | Report abuse |
  11. Jerry

    Mr. Anderson, you disappointed me in your discussion of Mr. Hefner and his cancelled marriage. You, Mr. Anderson, are guilty of age discimination.

    June 15, 2011 at 1:29 pm | Report abuse |
  12. John Q Public

    More like a January to December romance or more accurately a BC to AD romance.

    June 15, 2011 at 1:37 pm | Report abuse |
  13. Patrick Prince

    Age shouldn't count as far as marriage is concerned ,the important thing is if love is felt, shared and enjoyed by both parties.In this case there may be more hidden truth to the punch before the time likely to save Hugh from the side effects of viagra overdose.

    June 15, 2011 at 1:39 pm | Report abuse |
  14. ourbedofnails

    Okay, while a lot of sniping about Hefner is to be expected (and probably deserved as well in his case), there is evidence that intergenerational relationships between an elderly male and a younger fertile female is desirable. Whatever genetic material has contributed to a man living to a ripe old age cannot be passed on to future generations via his mating with a post-menopausal woman. Thus, these intergenerational relationships may be exactly what Mother Nature intended.

    June 15, 2011 at 1:45 pm | Report abuse |
  15. Bubbles77

    Both Heff and Harris annoy me because I mean she probably never wanted to love Heff and was probably just carrying the torch of all Heff's playboy playmates. And Heff could find somebody his own age couldn't he?

    June 15, 2011 at 1:47 pm | Report abuse |
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