Dating Over 40? No Worries! 15 Reasons Single Men Prefer Us!

dating over 40

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author


In my “Love Essentially” column that appears today in Chicago Tribune Media Group publications, I interviewed 5 men over the age of 40, asking them about dating over 40, and what aged women they prefer. Guess what they said? They like women over 40!

15 Reasons Single Men Prefer Dating Women Over 40 

Ask any single woman over 40 if it’s hard to meet a man and you’re sure to get an earful. In particular, she’ll tell you that there are so few good guys available over the age of 40, and that even if you weed out the losers and the ones with heavy baggage, the normal, nice ones don’t want HER, they want a woman in her 20s or 30s.

Well, guess what? That is just not true. Many men prefer sophisticated, smart, sexy older women to younger women who haven’t really lived yet, and I have proof!

I reached out to five different men between the ages of 42 and 55, and combined, they gave me…

15 reasons they prefer to be with a women who is around their same age:



1). Women dating over 40 know who they are and are generally comfortable in their own skin.

2). What women in their 40s have over their younger counterparts is that they are perfectly – miraculously – well calibrated to men their own age. They share maturity, life experience and even pop culture references, they often have similar-aged kids, parents and even gym habits, and most importantly, similar life goals and horizons.

3). It’s effortless to talk. There are no awkward pauses trying desperately to think of something to say.

4). If I’m with a young woman and I mention something about Pink Floyd or REO Speedwagon, chances are she won’t have a clue what I’m talking about.

5). You can really be yourself. It’s OK if you are getting gray or getting a spare tire, or prefer a quiet night at home over a loud club.


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6). My kids are older and I have a lot more time and more freedom. So if I’m dating an older woman, her kids are most likely older and like me, she has time and freedom.

7). The next morning (if there is one) is not about someone taking “the walk of shame” or rushing to get out. You can go to breakfast, maybe do a crossword puzzle together or laugh about the night before.

8). There is no paranoia. Often when you date a younger woman you feel like she is kissing you with one eye open and looking for other, better opportunities. For the most part, women over 40 are looking for true love and will give you undivided attention.

9. Going out with your friends is not awkward because they are her age, as well.

10. What do you talk about with someone who is 25 years younger? You can’t relate to them on any real level.

11. Then there’s the creep factor. My son is 23. I have no interest in dating someone his age.

12. We’ve had similar life experiences because we grew up in the same era. That emotional bond and level of maturity is priceless.




13. Dating someone younger may be fun for the short term, but without an emotional bond, it won’t last long.

14. Women dating over 40 have traveled, they’ve had a career, they’ve had children, and they’ve probably experienced tragedy. They are so much more interesting.

15. There has to be chemistry, but I can much more attracted to someone who is older if the emotional chemistry is there. In other words, it’s not always about the best body or a wrinkle-free face.


I chose to keep all of these men anonymous, but I want to share that 2 of the 5 guys are currently in a serious relationship, both with women over 40.

So, next time you are feeling hopeless in dating over 40, and thinking that Mr. Forty Something Right doesn’t exist, think again. Not only is he out there, but he wants YOU!


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

One Response to “Dating Over 40? No Worries! 15 Reasons Single Men Prefer Us!”

  1. Mark White

    What makes you so sure a man is a loser? A small bank account, or none at all? Health problems? Looks his age? Weed out too many men and women will find there aren’t enough left to go around!


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