Dating Younger Men

Dating Younger Men


Why is it so much harder to accept the idea of successful, older women dating younger, less successful men than when the genders are reversed?


nejron / 123RF Photo

We all know the scenario of the older wealthy man with the younger hot babe. If you live in Los Angeles, it’s practically the norm. We’re more apt to react with surprise when we hear about people getting together who are “age appropriate” because it’s common in this town for the man to be 10, 20 or more years older than his girlfriend. Older rich guy, younger attractive woman – so what?

What remains more of an enigma is when it’s the woman who’s the older and more successful partner in a romantic relationship. Sure, we’ve heard the term gigolo, but that’s more of an hourly wage scenario. What I’m talking about is a relationship, not a male escort. There’s real romance underway that’s not any less “real” than those relationships where the genders are reversed.

It’s different from a “cougar” situation, too, because this is more about influence than sex. And just like the more common older man/younger woman paradigm, most people would agree that it’s highly unlikely the two of them would be together if money, power and prestige were taken off the table.

Take my girlfriend Christie. She’s single, in her early 60s, extraordinarily successful, smart, attractive (no dances with the plastic surgeon yet) and has zero interest in men her own age. She only wants to date men who are on the south side of 35 and look like Calvin Klein underwear models – and if that’s what she likes, why not?

“Men my age can’t keep up with me. They look so old. I would feel like I was dating my father,” she says, showing me a photo of the hunk she’s having dinner with on Saturday night.

Despite my laissezfaire attitude about most things in life, every time she tells me about one of her new love interests, I worry he’s only after her money or connections. Why is it so hard to believe that these men are fascinated by her sophisticated elegance and worldly charm? I don’t react like that, nor do most of my friends, when my older guy friends show up with a younger woman on their arm.

Funny how preconceptions about age and gender – like the bias against people who are single – can sneak into our subconscious and color our perceptions. As aware as I try to be, particularly since I became aware of the prejudice that exists in our culture about being single, I’m still guilty of slipping into judgment based on stereotypes that have me leaping to conclusions before I know the whole story.

Fact is, if my female friends want to date and mate with men who are much younger, even if there’s a certain element of quid pro quo in place, why not? We are talking about adults here, so let the buyer beware. And most likely, that buyer, if she’s managed to create a successful career and business, has tangled with trickier situations than a stunning, much younger dinner companion.



After 12 years together, Barbara Hershey and Naveen Andrews, with a 21- year difference between their ages, ended their romantic relationship, but still remain friends.


Brazilian model Jesus Luz became Madonna’s boyfriend shortly after her divorce from Guy Richie was finalized. There is a 28-year-difference between them (his mother is 14 years younger than Madonna). No longer a romantic item, Luz claims he initiated the split because of a lack of mutual interests.


Cher likely holds the title for having the most “much younger” boyfriends. She’s pictured here with Rob Camilletti, whom she has described as “the one true love” of her life. Camilletti, 18 years younger, met Cher at her 40th birthday party. The two were together for three years before an amicable split. They remain friends.


Ashton Kutcher met Demi Moore when he was 25 and she was 41. Two years later they got married, bringing hope that yes, younger men do fall in love with older women – and marry them. It was Kutcher who filed the divorce papers, citing irreconcilable differences, and the couple reached a settlement in October 2013.


Ellen Barkin was 56 when she started a relationship with film director Sam Levinson, who was 26 at the time. After dating for two years, Barkin moved Levinson into her house in Manhattan and reportedly asked him to marry her.


Ivana Trump married 23-years-younger Rossano Rubicondi, her fourth husband, in an elaborate $3 million ceremony in 2008. They divorced the following year. Despite the split, they still enjoy a romantic relationship and were seen last summer vacationing together in Sardinia.


Joan Collins says her 32-years-younger husband, Percy Gibson, was a good friend for about 10 months and then one day became something more. Married for 12 years, Collins, now 81, once told friends concerned about the age difference, “If he dies, he dies...”


Together since 2009, Susan Sarandon is 30 years older than her boyfriend, Jonathan Bricklin. In an interview with Katie Couric, Sarandon said she doesn’t think marriage is for her. Sarandon also told Katie she hates being labeled a “cougar.”


Virginia Madsen has been dating 20-years-younger Nick Holmes for several years and the two are often seen together on vacation, at movie premieres and film festivals.


Copyright © Kim Calvert/2014 Singular Communications, LLC.

Kim CalvertKim Calvert is the editor of Singular magazine and the founder of the SingularCity social networking community. An outspoken champion of people who are living their lives as a “me” instead of a “we,” Kim oversees the creative direction and editorial content of the magazine and online social networking community. She secures contributors and is responsible for maintaining the fun, upbeat, inspirational and often-humorous tone of Singular, a lifestyle guide for successful single living.

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9 thoughts on “Dating Younger Men

  1. To the editor Kim – as always your recent editorial is provocative. My further comment is that there is something that is hard to articulate about the older female to younger male that possibly relates to the “Oedipus complex” more than the converse to “Electra complex”. It’s not exactly “tabu”, yet tacitly seems so.

    I recall ions ago when the English designer Mary Quant was the “older” woman in a relationship to a man whose name I don’t recall, however it could be researched.

    As an ingenue I was always attracted to “older” boys or men which I attribute to experience and/or sophistication that is more alluring. I’m no “Kamali” or sensual mentor. The comment I found interesting is your friend’s statement about keeping up with her, i.e. energy, intelligence, etc.

    The maturity level of today’s younger generation in general is lacking so in that sense it makes “older” men even more appealing, though maybe not so “frisky”.

    In essence if the real attraction is there, and compatibility, then who cares about age, and like my later Mum I’m…… Signed,


  2. I,m very happy at the moment take each day, as it cams,my best friend is 27 Years old and I 74.
    I meet him personel on Holiday last Year January and we on FB evry night and hat Holiday with him last Sep. – October for 1 week, we very fond of each other. I say live ur live as it is ur last day, I dont mind be see with junger man. I always likt junger man to keep up with me, I,m sportiv and luke after myself.

  3. Since my divorce, I have found the majority of guys interested in me are either five to twenty years younger (and even younger than that!) or guys fifteen to twenty years older. Today, age is a function of energy and where you are in life. I am in great shape and have a long list of goals I still want to accomplish. I prefer not to be with someone who is not in shape or is finished, no matter the age. Sexy, confident, in shape women can attract younger men just as readily as some sixty plus guy can date a twenty-something girl. It’s 2014!

  4. I want to start online dating. I’m 54 but most people think I’m in my early 40’s. I almost always date younger men, 7-15 years younger. I’m concerned that I won’t find such matches online. Any advice?

    1. Go to SingularCity events and meet people in real life on a casual basis, without a dating agenda, and then just see what might develop. If there’s romantic chemistry, it will happen. If not, you’ll still have a great time.

  5. I have 2 girlfriends who would only date younger men,
    This was 25 years ago, so this has been gong on under the radar for a long time.
    One girlfriend married her current husband 20 years ago and they are incredibly happy.
    He is 30 years younger than she is. Since she was not rich, inredibly beautiful or extremely sucessful, that leaves only one reason he married MaryAnn, that can only be LOVE!
    I myself prefer my own age group or even older but………………

  6. It’s really nobody’s business who you date. As long as both people are consenting adults. And certainly, if it’s ok for guys to date younger women it should be ok for older women to date younger men without being called a cougar.

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