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.

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

    who cares if she backed out the test drive was worth it...

    June 15, 2011 at 2:02 pm | Report abuse |
  2. Darcy

    Oh yea – her lawyer finally explained to her what the prenup actually meant. If you divorce or even if he dies in your bed you do not get to be owner/operator of the Playboy empire. In other words – you'll go from shopping on Rodeo Drive to shopping at Wal-Mart. She understood THAT loud and clear.

    June 15, 2011 at 2:05 pm | Report abuse |
    • sirkanth


      June 15, 2011 at 4:17 pm | Report abuse |
  3. Insight4Real

    Any woman that is dating a guy more than 20 years older is just really bad at math. On average women live 15 years longer than men. Add the 20+ year difference of your ages and you will spend at least the last 35 years of your life alone. if you can't get a man your age when you are young, try getting it when you are 60+. Those guys are either going to be with someone or going after younger women. It's up to the woman to say no to this, they guys won't stop doing it, they get the younger women and all the benefit, you get to die alone. But if you are okay with that, go right ahead.

    June 15, 2011 at 2:06 pm | Report abuse |
    • juicius

      I'm pretty sure you can get cats no matter how old you are.

      June 15, 2011 at 2:13 pm | Report abuse |
    • flower

      If a reach man leaves his woman wth millions of dollars after his death, a woman can find ANYBODY even if she is old and ugly. LOL.

      June 15, 2011 at 3:22 pm | Report abuse |

      Do you REALLY believe she was going to marry him to BE with him? This is stupid to even think this way. She married the MONEY. The guy is falling apart. He is probably older that her grandpa

      June 15, 2011 at 3:29 pm | Report abuse |
    • EmptySkull

      For her purpose, the older the better! That means the sooner she'll become a widow and start inheriting and looking for another guy

      June 15, 2011 at 4:19 pm | Report abuse |
    • Jorge

      Hey, don't knock it 'till you've tried it. When I was 38 (and 1 year divorced) I lived with a heart-stopping (to me) 18 year-old co-ed for a couple of years. What she got in return (among other things that I will not mention) was a whole lot of material and emotional support during her hardest time (said by her) a lot of street smarts, academic help, free room & board and countless weekends at my country house just decompressing and swimming on the lake. My insanely jealous daughters, about her age, finally wore her down and we decided to break up. We still call on each other when I go back home, except that now she's a career woman and SHE chooses to pay (I still have to keep it from my daughters, though).

      June 15, 2011 at 4:43 pm | Report abuse |
    • Insight4Real

      @flower – lol, maybe... But most men are a lot more superficial than that, sure you can get a few that will chase the dollar. Even if they take it, I think that the woman might want more than a souless physical relationship. It seems the guys are okay with buying that, not sure that the woman would be.

      June 15, 2011 at 5:38 pm | Report abuse |
  4. Wal-Mart

    Jazzzzzzz. Dear customer,we do not offer green snot as any of our products. Please do not call any Wal-Mart store for this reason anymore. Sincerely, Wal-Mart Family.

    June 15, 2011 at 2:09 pm | Report abuse |
  5. Anne

    Viejo Verde

    June 15, 2011 at 2:09 pm | Report abuse |
    • Jorge

      Hasta la muerte, mi amor.

      June 15, 2011 at 4:45 pm | Report abuse |
  6. juicius

    May-December romance... Yeah, December the year after.

    June 15, 2011 at 2:12 pm | Report abuse |
  7. Robert Posey

    Really, Really sick, marry at least close to your own age, or just rent.

    June 15, 2011 at 2:54 pm | Report abuse |
  8. awdam

    I bet she got scared when he whipped out a borrowed congressman's weiner!

    June 15, 2011 at 3:05 pm | Report abuse |
  9. jj

    Hef claims there was no prenup. But he surely had the majority of his fortune safely tied up.
    And Crystal is such a beautiful woman – yet she looks a bit like a guy. Not that I'm complaining!
    And good luck to her. I don't think marrying Hef would be that bad – you know what you're getting (except for the age – and maybe that expiration date the main appeal). Who would marry a Schwarzenegger, or a Gene Simmons??? They are controlling, womanizing creeps. With Hef, you aren't going to sleep with him much. And if he sleeps around, he's one step closer to that farewell heart attack...

    June 15, 2011 at 3:08 pm | Report abuse |
    • so

      so are you saying you like men?

      June 15, 2011 at 3:31 pm | Report abuse |
  10. jj

    "Love of his life..."??? Give me a break. This ole coot has been with so many women I seriously doubt he understands the concept of love, or commitment. Maybe if he considered a relationship with an actual adult woman he might find there are women who are lovely, intelligent, and interested in him as a human being and not as some iconic old guy they can hook up with to get their name in the press.
    I am sure his children must feel so good to hear him call his latest bimbo the love of his life. How disrespectful. He and Gene Simmons need to get a bachelor pad together.

    June 15, 2011 at 3:23 pm | Report abuse |
  11. lonewolf777

    Whatever works between people is their business. I never hear a man ridicule differences in age – it's always women.

    June 15, 2011 at 3:27 pm | Report abuse |
  12. aimexx

    Not quite that much of a difference but there are 13 years between my husband and myself. Things are find until (depending on health) that one of you hit 75. Hence the divide begins. The older person in the relationship becomes "elderly" while the younger person isn't. I've seen several of these relationships struggle based on age alone. It just does't work as we age.

    June 15, 2011 at 3:34 pm | Report abuse |
  13. bioya

    Great Strategy on her half, she probably said she was a "virgin"... and decided marriage was going to be a nightmare sleeping with, she now has "fame" turning down Hef, (Eat your heart out cry-baby Holly)

    June 15, 2011 at 3:40 pm | Report abuse |
  14. Logic

    May-December, more like January-December

    June 15, 2011 at 3:48 pm | Report abuse |
  15. jim

    "May-December romances"? What makes you think this has anything to do with romance?

    June 15, 2011 at 4:03 pm | Report abuse |
1 2 3 4