Older Guy Younger Woman: Can It Work?

I’ve never understood the older guy younger woman relationship. Why would a man over 40 want to date a woman in her early twenties? Here are the possible reasons, in my opinion.


  1. She’s hot.
  2. She’s fun.
  3. She’s got a lot of energy
  4. She makes him feel young.
  5. Deep down he doesn’t want anything serious, so she is perfect for him.
  6. She looks up to him and makes him feel important.
  7. He is proud to have her on his arm.


All that said, I do think there is a side of a man who dating a much younger women that at some point thinks to himself, “What the hell am I doing?” Case in point—I received this message from a reader:

The Center for Divorce Recovery

So I’m dating a girl who is 23 and I’m much older. What’s the downside? We both enjoy the relationship.


Now, why would this guy reach out and ask about the downside if he is saying “We both enjoy the relationship?” Why does he care? Does he want validation from me? Does he need me—a 50 year old woman to tell him I approve? Maybe he just wants my opinion, which is this.


If both of you are having fun, I think there is absolutely nothing wrong with what you are doing. If no one is getting hurt and if there are no false expectations on either part, then I think it’s great. Just enjoy it.


To answer his question, “What’s the downside?” In my opinion, deep down, he knows, but I’ll say it anyway. The downside is, these kinds of relationships have a shelf life. Older guy younger woman only lasts for a period of time and then it just doesn’t work anymore. Why?


  1. The novelty of the relationship wears off and they realize they have so little in common.
  2. They run out of things to talk about.
  3. The guy realizes he wants someone to grow old (older) with.
  4. The girl realizes she wants babies.
  5. They realize the relationship is not ever going to be as deep as they want it to be.


It’s sad because when any relationship ends it hurts, and despite the age difference, if you spend a large amount of time with someone, you begin to care for them, and ending it hurts.

Also, I’m not saying that every older guy younger woman relationship is doomed. Some work out but I think it’s rare.

I have many guy friends who are in their forties and fifties who tell me they prefer to date women around their age. Their reasons stem mostly from the comfort and commonality they feel with someone of a similar age.


In closing, the other day, I happened to see a man in the Nordstrom lingerie department who looked like he was around 60. He was browsing the Valentine’s Day rack of black, lacy thongs, teddies and garters. It appeared to me that he was shopping for his twenty something girlfriend. I’m not saying I’m right, but there wasn’t one thing on the rack that would be worn by a woman over 40. And by the way, I’m not judging him at all. My point is, older guy younger woman relationships are still rampant, and I truly think lack of commitment is the biggest attraction for that demographic.

In other words, I think it comes down to whether or not the two people are truly interested in a long-term commitment. If a person is, he or she is most likely dating someone within 10 years either way of their age. In my opinion, the Nordstrom guy is on cloud nine, but he has no intention of marrying the recipient of his Valentine’s Day gift. Good for him. I mean that sincerely. Everyone should date who they want and not care about the stigma and judgement of others. But I really believe that when it comes to true love and long-term happiness, older guy older woman will beat out older guy younger woman every time.


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

2 Responses to “Older Guy Younger Woman: Can It Work?”

  1. Ethan

    I like this article and I think it’s 100% true except I want to correct one small part. At the very end you say:

    “But I really believe that when it comes to true love and long-term happiness, older guy older woman will beat out older guy younger woman every time.”

    To clarify, long-term happiness should not be reliant on ANY romantic relationship. And I also think that the wording of “true love” should be “long term love”. It is not our place to define what love is true or not.

    As for why the guy emailed in? I think it’s for the same reason I am here. He wanted to validate that what he was doing was ok, because a large part of society looks down upon age-gap relationships. I really appreciate the following you put in this post, and it’s important for all people who feel judged by society to remember:

    “Everyone should date who they want and not care about the stigma and judgement of others.”

    hear, hear!

  2. KJones

    Michael Douglas and Catherine Zeta Jones, Jason Statham and Rosie Huntington Whitley. Humphrey Bogart and Lauren Bacall. Harrison Ford and Calista Flockhart. Etc. It’s inherently dishonest to say that an older man/younger woman relationship can never last.


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