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Midlife Dating: The Gentleman Goes A-Courting

Dating! Ah, the thrill of the hunt. Ah, the thrill of the thrill.I can only ... men by a mental ... like an analogy, but of course I’ve studied and had practice because my life is

Dating! Ah, the thrill of the hunt. Ah, the thrill of the thrill.

I can only understand men by a mental sleight-of-hand, like an analogy, but of course I’ve studied and had practice because my life is full of men and I also coach men. I get to hear what’s on their minds and in their hearts.

This is about men and midlife dating. We’re going to look at the research (and you can see if it’s true for you), and about what works and what doesn’t.

Having a great relationship takes emotional intelligence (EQ), and EQ begins with self-awareness. So here we go!


80% of you guys supposedly prefer to date women who are younger than you, and the older you are, the more younger you want the woman to be.

This fact is not popular with middle-aged women and causes tension. There are less eligible men to begin with, and only 20% want someone their age. Also, her husband may have run off with a younger woman. You may be empathic about this situation, but don’t do what some men do and tell her, “I want you to know I don’t date young women. I want a woman with something between her ears.” Though an attempt to reassure, it painfully accomplishes the opposite, like saying, “Trust me.”

It would be like her saying to you, “I know half the men over 40 have erectile dysfunction, so don’t worry. It’s okay with me if you use Viagra.”

Ouch. Get it?

Leave it alone. Just enjoy her and let it show. There are plenty of other things to talk about. She’ll find out how you feel about age by watching you, and she can take care of her own end of it.

If you do go there, which I don’t recommend, phrase it this way: “women younger than I am.”

If you ogle young women in her presence, you deserve what you get.


Do older man/younger woman marriages work? We know 60-70% of second marriages fail, but I can’t find any statistics on the fate of May-December marriages. I’m afraid this might be the reason why: We only do research on things we can’t predict.

To be fair no one’s studied the success rate of marriages where the woman marries for money. However, “rich” is hard to quantify, while “age” is one of statistics’ favorite measures.

Of course if you want children, you will need a woman of child-bearing age. If you want children, know at your core why you do. It is seriously wrong to bring a human being into the world only to prove you still can, or to regain your youth.


Men fall in lust, I mean love, visually. When he says why he loves her, the man mentions her appearance, or rejects her on the same basis.

However, an AARP survey found that men value different things in a “date” than in a “partner.” For both sexes, personality and compatibility come first for both date and partner, but men rate appearance and sexual compatibility higher for a date than for a partner. These are smart men. They know that a fun date may not make a good partner.

Men dating on the Internet demand a photo. They can’t wait to get to the ‘meeting her’ stage, holding back until they’ve laid eyes on this woman they’ve been corresponding with. They’re furious when they find the photo has misled them, but all photos do. They want to see her and get that zing. Is this true of you?

However, if we’re lucky, we mature with age. One man who conducted a 4-month courtship via the Internet told me with wonder that it was “like falling in love from the inside out.”

You might consider this concept as a formula for a viable relationship. Whatever you see in the woman LITERALLY is going to change. She may get wrinkles, her hair may turn white, she may gain or lose weight.

Whatever you see in the woman FIGURATIVELY is likely not to change. A woman of character has built it the hard way by the time she’s 50. If she’s loving, compassionate, faithful, patient, resilient and stable, it’s there to stay.

If you can’t “see” the things you can’t see and touch, you are going to fall in love with a figment of your imagination.

Or, you’ll get burned. “I guess I’ve got to quit messing around with hotties,” one man told me, and he wasn’t all that sad about it. He reached his own conclusion, so I assume he learned it the hard way.

“What she’s like” means how she feels about herself, how she treats others and you and your relationship, what her values, ethics and standards are, what she believes in, what her priorities are, what gives her life meaning, and how compatible her interests are with yours. This you learn by being with her and observing her in different situations with different people across time, and I don’t mean observing her booty.

The gentleman who was discovering “falling in love from the inside out” had had a series of relationships with much younger women that had imploded. Although I left it to him to connect his own dots, he had fallen in love with them from the outside in. Forced by the constraints of the Internet and a woman with good timing, he had inadvertently stumbled on doing something different, and it had a happy ending.


When another man had found the woman he wanted to marry, he told me, “She wasn’t much fun to date. She was responsible about her kids and parents, her home and her job. She was always involved with them. But when I got on the inside of that it was okay.”

That may be the understatement of the year.


It’s more difficult for men to know what they’re feeling and to express it. It can take a man hours to figure out what he was feeling at the time. When it all gets to be too much, you go into your cave.

Expect this to be understood. Women at midlife know a lot more about men. They know this concept of “going into the cave.” Great! You no longer have to explain what you can’t explain or you wouldn’t be going to your cave.

In fact, some man whose name I can’t recall wrote an article about why he preferred women over 40, and said, paraphrased: ‘They don’t wake you up at night to find out what you’re thinking. She doesn’t care what you’re thinking.’

You, of course, will reciprocate by letting her talk about her feelings and not trying to “fix” them, right?


When these “hunters” who talk to me find the one for them, this is the language they use: comfortable, safe, joy, trust, comfort, coming home, soul-mateArticle Submission, and heart’s darling.

This is not thrill and zing and sexy legs language. This is language about a solid foundation you can build a life around.

Think about it.

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©Susan Dunn, MA, Midlife Dating Coach, . Offering coaching, Internet courses and ebooks for your personal and professional development, relationships, career, midlife transition and dating. She is the author of “Midlife Dating Survival Manual for Women.” For more information or free EQ ezine, .

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