The Story Of An Older Woman, Younger Man

I said I would never, but I did.

I commented on a very interesting article about the appeal of older women, written by Everyman. My response seemed to resonate with others, such as Kimberly Carlson Aesara, and at the request of several, I have expanded that comment into “the rest of the story.”

In my 50s, single for the first time in my adult life, what I discovered, much to my surprise, was that the men who sought me out, who asked me out, were invariably much younger.

I had not anticipated that.

I had been married since I was a teenager, and was totally unfamiliar with the dating game. While my generation was attending college and partying like rock stars, I was at home raising babies and running a business.

I made some very naive mistakes. Life in a monied, sophisticated, fast-lane lake enclave is not for the faint of heart. The unwary are chewed up and spit out on a regular basis.

But I didn’t know that then.

Blessed with good genetics and a slender, well-proportioned, and toned body, I looked much younger. I had a dancer’s grace and confidence. Looking back, despite the fact that nobody in my life had ever told me so, I realize now that I was a beautiful woman.

That didn’t hurt my prospects one bit, I imagine.

People made some unkind (a cynic might say envious) remarks about being a “cougar,” but the reality was that it was the young men who were asking me out. I didn’t seek it, they just came.

I was as surprised as anyone else. Perhaps even more so.

What is the attraction?

In retrospect, I believe part of the appeal was that I was a professional with a solid career. I was educated and secure in my own skin. I think an older woman often has a certain confidence and maturity that some men find intriguing. She comes across as stable and independent.

The way she carries herself shows that she knows who she is, what she wants, and is comfortable with it. It takes time to reach that stage in life.

A guy 16 years my junior, with whom I had a glorious, if short, relationship, once asked me if I had always been this confident in my sexuality. I truthfully answered, “No.”

I was not confident at all in my 20’s and 30’s, but at 50, I damn sure was.

I was also educated and intellectual. I was settled. Financially secure. I had lots of life experience.

Those qualities are apparently a powerful aphrodisiac.

What were the alternatives?

To some extent, I discovered that if a man was running around loose at midlife, there was usually a very good reason for that. If not, the other single ladies were as viciously competitive for his attention as a bunch of 7-year-olds attacking a pinata at a birthday party, and he was snatched up quicker than you can say Jack Sprat.

I found that men my age were usually interested in chasing much younger women; if not, they were just too old for me, in spirit, at least. I was (still am, actually) healthy and fit. On our first date, one prospective suitor went on and on AND ON about his root canals.

No second date for you, Skippy! God bless.

Another sweet guy I went out with once, in an attempt to further his advantage, I assume, shared with me that “younger guys are just attracted to the sexual experience of an older woman.” He had heard this discussed at the GM plant where he worked.

Perhaps that’s true. However, I didn’t necessarily see it as a bad thing.

At dinner, he also advised me that his family frowned upon drinking anything stronger than sweet tea. When he saw the look on my face, he hastily added that he would overlook it if I had a glass of wine now and then, though.

I never had a younger man say that.

Then there were the bachelors and only slightly married men who milled around town in a herd, ever on the lookout for fresh pickings. And there were all of the extremely territorial women of a certain age, both single and married, having already staked out the turf, who looked at me as if Jezebel had just walked in the door.

It was a regular minefield.

Perhaps a younger man may feel that an older woman is more sexually confident. My husband once said, in regard to one night with an older co-worker at age 15, that, although it wasn’t his first rodeo, he “became a MAN that night.”

You should see the look in his eyes when he talks about it, even after all these years.

Alrighty, then. Let the games begin.

When at last I met and began seeing this man who was 12 years younger, I found it interesting that the men my age began to seem jealous and protective, as if he had something they wanted and didn’t have. Women his age, or younger, tended to view the relationship a bit askance.

Some thought he might prefer them, instead. Sometimes, they still do. More power to ya, honey.

That man is in love with me.

We lived together for 5 years, and then I married my much younger man 10 years ago. Neither of us is easy. It works because I find him enormously attractive, and he has always preferred older women. A younger woman wouldn’t be able to handle him, quite frankly.

It does have its drawbacks.

He is gorgeous and sexy as hell. Truly, he is.

I ask him sometimes if he wouldn’t rather be with someone younger, perhaps even have had children. He always looks at me as if I’ve lost my mind.

“I don’t want anyone else, Darlin’. Only you. You are the love of my life.”

So now, I am officially out of the race, and glad to be. I’m riding around the world on the back of his motorcycle, much to the horror of my children.

But that was an enlightening time in my life, for sure. And I certainly can’t argue with the results.

© Conni Walkup Hull

Thanks for reading.