Midlife Dating: Men, What Say You?

shutterstock_268928468I gave the guys a little dating tough love in my last blog post, so it’s only fair to give the guys some equal time to speak on the state of the midlife singles scene as they see it.

I wanted to know how post-50 men feel about dating, so I gathered up a few of my middle-aged guy friends, bought them a few beers, and picked their brains about dating: the good, bad, and ugly. They were buzzed just enough to tell me.

Their feedback was insightful, honest, and very real. It was also cringe-worthy, because as a former long-time single girl (up until very recently) I made a lot of dating mistakes, and I felt they were describing me.

Now I know what you girls are thinking: By the time you’re in your 50s and single, everyone is bitter, jaded, or hardened about dating, so why should I listen? If they’re still single, they’ve probably struck out at love.

Some have struck out, but who hasn’t? If you’re single and post-50, you’ve probably seen it all, done it all, and chances are, you’re down on on the whole thing. Join the club! Everyone in the 50-something dating pool has had their fare share of breakups and fuck-ups, but that makes you human.

True, dating in your 50s can blow, but it doesn’t have to suck.

In fact, midlife can be a great time to be single, and my man friends here agree. These are nice guys, not shallow, not players, they’re looking for LOVE, not games, or one-nighters, younger chicks, or the bigger, better deal. They’re looking for smart, substantial, age-appropriate women who know who the Beatles are.

In other words, they want women like YOU. So ladies, if you’re listening, take note.

Note to the men: This stuff works both ways, so listen up.


“I actually prefer dating women my own age because we have a common base of things to relate to, talk about, laugh at, or commiserate over. Women my age ‘get it.’ Very little gets lost in translation. Put it this way, if a woman isn’t familiar with Woody Allen’s early work, then it couldn’t possibly work.”

“Women in their 50s generally have more time and freedom. They’re more relaxed, especially if they’re empty nesters. We’ve been both been through the hell of raising young kids and now we can hang out.”

“Women over 50 are the sexiest humans in the world. They’re in command of their bodies, and in charge of what they want and need. They don’t care about stretch marks or a few extra pounds – and neither do I. Besides, I’ve got a big gut, so who am I to talk?”


“Women in their 50s can be a little too anxious to get involved. Right after the first date, they want you to meet their kids, their parents, their pets, whatever, without any regard to your comfort level. It feels rushed.”

“I’ve dated some divorced women in their 50s who are so bitter and angry toward their exes they can’t see straight. It’s hard to get close when she’s still fuming.”

“You can feel the desperation with some women in their 50s, especially if they’ve been single a long time or if they’re newly divorced.”


“If a woman tells me what to do with my kids, or gives me unsolicited advice, or criticizes my parenting skills, I run for the hills.”

“Women who obviously judge you based on how much money you make, or in my case, don’t make, is a deal killer.”

“I’ve met some women in their 50s who believe having sex as quickly as possible is a way to get a man and it’s not.”


Men who seek out and date women in their 50s do so because they WANT TO. Because they dig chicks who have a little more maturity and experience; because they enjoy the mutual compatibility and sympatico you get with someone your own age; because there’s more freedom and fun; because women in their 50s are hot as hell, and yes, they’re menopausal.

Ladies, I’m not telling you what to do, but here’s what I’ve gleaned: If you stay open to the possibilities, TRY to have a good attitude, make peace with yourself, let go of anger, and don’t jump into the sack too soon, you’ll see that midlife dating doesn’t have to blow or suck at all.

But maybe that’s not a bad thing?


Guys and gals, what say you? What’s the state of your singles scene?

8 replies


  1. YouSoundSingle
    YouSoundSingle says:

    I am only 20 years old but in all honesty the responses and advice given in this piece are relatable for my age group as well. Wanting someone your own age, the disagreements about how soon to commit or how soon to have sex are all things I deal with also. As someone just starting to figure it out, I appreciate this a lot.

    • Treva Brandon Scharf
      Treva Brandon Scharf says:

      Kimberly, the guys in my article are the real deal, and they’re everywhere, not just in my post. For every woman who says there are no good guys out there, I’ll show you a good guy who’s interested in a woman just like her. I met one at 50, he was 56. We both had baggage and a past, but who doesn’t at that age? We’re not perfect, but we’re perfect for each other.

  2. Generic Man
    Generic Man says:

    I am a bitter man. Why? I’m healthy, peaking in my career, am not a creep, but am one of the 10s to 1 ratio of men all chasing (I am not chasing) after the same women. And I am not good looking. I’m not bad looking, don’t have an old man belly, and am in shape. I am groomed, dress well, and am polite (I hold doors for everybody). I don’t want a FWB, meaningless sex, or desire to date multiple women at the same time.

    But it sucks that I am invisible. And it sucks even more to be rejected by equally or more unattractive women.

    The end result is I have to change my thinking and it’s difficult because at 54, there are not many women out there that are truly available.

    • Treva Brandon Scharf
      Treva Brandon Scharf says:

      Hartfordfirefighter, why be bitter when you’re healthy, professionally peaking, well-groomed, attractive, and in shape, as you say you are? Sounds good to me! Do yourself a favor and re-read your words as many times as you can, then start believing it. Own it. Be that guy. There are TONS of women looking for someone like you, so keep yourself out there. Keep a smile on your face, keep your sense of humor, and keep the faith. P.S. Stop calling yourself generic too. You’re not.


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