The dating market for midlife men is fascinating right now because men and women are walking into it with completely different expectations. While I’m a happily married guy, I work with and coach a number of recently-divorced men, so I’ve got some insight into what’s happening, which is this:

A lot of accomplished men hit their late 40s or 50s thinking the hard part is over. They’ve built careers, accumulated some money, survived marriages, raised kids, collected stories, and they assume all of that automatically translates into value. Then they get divorced or separated, jump back into dating, and are genuinely shocked by what they find.

Not the attention. Most men with a little money and a little confidence can get attention. Quite a bit actually. 

What surprises them is the quality gap.

Because while a lot of these guys were coasting through comfortable marriages, drinking too much, neglecting themselves physically, emotionally and intellectually, a lot of women in midlife were doing the exact opposite. They got healthier. Smarter. More independent. More self-aware. More financially secure. More certain of what they will and won’t tolerate.

And now the two groups are meeting each other again.

Chelsea Handler talked about this recently on a podcast when she said it’s hard to find straight men who have their act together. She said she doesn’t know what’s wrong.

I do.

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I actually went down to The Improv on Melrose last week where she was performing because I wanted to talk to her about it. The conversation never happened. She slipped out before I could corner her into a discussion she absolutely did not ask to have, but she put on a great show and honestly, I understood exactly what she meant.

The dating market for midlife men isn’t broken. A lot of the men are.

Not bad men, either. That’s the important distinction. Most are decent guys. But too many got comfortable, then complacent, and eventually stopped becoming anything.

Meanwhile, quality women kept building.

That gap is the whole story.

I know a lot of amazing men. Almost all of them are married. There’s probably a reason for that. And of the recently divorced or separated guys I know, men I genuinely like, I really had to stop and think when a woman recently asked me if I knew any “good men” to set her up with.

She was successful, sharp, attractive, fit, a mother of two, and someone I met through mutual friends at an event where I was speaking. She later DM’d me and asked, very respectfully, if I knew anybody worth meeting.

And the truth is, liking a guy and vouching for him as a dating partner are two completely different things.

I also get approached by matchmakers all the time. I think they assume I’m coaching this deep bench of eligible, emotionally available, self-aware midlife men who are ready for real relationships. The reality is our readership is more than 90% married. I currently have one single guy I’d confidently describe as a legitimate catch.

One.

So what’s actually happening out there?

The single middle-aged men I do know generally have options. Plenty of them. The reality is that if you’re a halfway decent-looking guy with some money, the ocean’s wide open. And even if you’re not particularly attractive but do have money, the number of attractive women willing to date you, and sleep with you, is honestly shocking.

We’ve all seen it. The older guy with the younger woman. Over and over again.

But volume was never the goal. At least not for the men who eventually figure themselves out.

A lot of these guys come out of long marriages feeling ignored, underappreciated and starved for attention. Suddenly they’re getting validation they haven’t felt in twenty years. Of course it becomes intoxicating. They date younger women. They collect stories. They stay out too late. They act like kids who just got let loose after decades of responsibility.

For a while, maybe it even feels like freedom.

Then eventually it starts feeling repetitive. And lonely.

A man who comes out of a long marriage and immediately goes into full quantity mode is usually telling you exactly where he is emotionally. Men with real substance eventually start looking for substance. They stop treating dating like fantasy football and start wanting an actual partner again.

That’s where this whole thing changes.

Because by the time these men finally look up and decide they want a high-quality woman their age, they’re now competing for women who spent those same years evolving.

Those women didn’t spend the last five years standing still.

They got sharper. More grounded. More successful. More disciplined. More emotionally healthy. More comfortable alone. They built lives they genuinely enjoy. And because of that, they can spot a stagnant man almost immediately.

Not because they’re “too picky.” Because they’re paying attention.

A woman who spent years becoming her best self can usually identify a man who stopped trying within the first ten minutes of dinner.

And that’s the part a lot of men still don’t understand. The bar for middle-aged men is unbelievably low. Embarrassingly low, honestly. Plenty of women will still date you there. But the women worth building a life with usually won’t.

They raised their standards while you stopped raising yours.

So the question I ask every man I work with, married or single, is pretty simple:

Are you proud of the man you are becoming?

Not who you were at 35. Not your title. Not your old stories. Not the version of you that existed inside a marriage where everybody got comfortable.

Who are you becoming right now?

Because the men who succeed in midlife relationships, whether it’s their first marriage, second marriage, or dating after divorce, usually have one thing in common: they never stopped growing.

They stayed curious. Stayed disciplined. Stayed engaged with life. They kept themselves up physically, emotionally, intellectually. They continued becoming someone.

The men who struggle aren’t usually bad guys. Most are decent men who slowly drifted into complacency and then got confused when the women they actually wanted no longer found them compelling.

The answer isn’t complicated.

Quality recognizes quality.

And it recognizes the absence of it too. 

In Health, 

Greg Scheinman

Founder, Midlife Male

Husband. Father. Entrepreneur. Coach.

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