Think Men Over 50 Only Date Younger Women? Think Again.

men over 50 only date younger women

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

I’m not sure why, but so many women I know who are dating over 50 assume that men our age–men over 50 only date younger women. While I do think there are some men in their fifties who prefer to date women in their thirties or forties, I believe there are countless men over 50 who prefer to date women their own age. Including this reader:


I’m a 53 year old male, healthy and active, and I would much rather have a 50ish lady than a younger woman. Why? Connection, experience, and freedom to do things and have fun.


If you think about it, it really does make sense.



People connect when they have similar interests, when they have the same taste in things like music or movies, and when they enjoy doing similar things. For example, a couple in their fifties might enjoy long walks on beach versus a 5-mile run like a couple in their thirties. Before you get all defensive, I’m not saying that no one in their fifties can run 5 miles. I’m just saying that in general, people enjoy doing different things at different ages. A couple in their fifties might like to listen to old music whereas a younger couple might prefer songs that are popular now. And, a couple in their fifties might have a different vacation idea than someone in their thirties. The younger couple might be more adventurous, while the fifties couple might want to relax. That said, I find that couples in their fifties are huge international travelers, whereas younger couples might not be ready for that yet, or might not have the time off to do so. My point is, couples who are similar in age have more of a chance of being on the same page when it comes to how they choose to spend their time together.


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From someone who dated someone much younger than me, I can speak about running out of things to say, not really being able to relate, and just feeling not-so-connected because of what I had been through and what he hadn’t. That’s not to say I didn’t adore my much younger guy (it was several years ago) but there came a time when both of us realized that we were in such different places in life. I was divorced with young kids. He had never been married and did not have children. He had a full-time job. I was a stay-at-home mom. I remember once I bought a new purse and I showed it to him and asked, “Do you think this looks like a diaper bag?” His response: “What’s a diaper bag?” I swear I’m not kidding. I think couples who are similar in age just get each other more. We’ve been through some similar life experiences, we understand what it feels like to raise kids, to age, or to have friends become ill or get sick, to hear about people we know dying, to care for our parents, to have parents become ill or die, and other things that happen when you are older versus young. And, there is something very comforting about being with someone who shares your experiences. You can relate. You understand each other without having to say much.  You are less judgmental. And, I think older people are less afraid to be vulnerable and authentic in relationships, which is truly beautiful.






I think what this reader meant by “freedom” is that older people might be retired and they are usually empty-nesters. What that means is basically we have more time. (not sure why I am saying “we.” I still work and have kids at home and I’m 53.) But my point is, I think it would be difficult for me to date a man who had toddlers. Not that I don’t adore kids, but it would be a hard adjustment. Plus, many older people love to travel and need the flexibility. If one person has it and the other doesn’t, that would put stress on the relationship. Couples who are similar in age can plan things more easily.


The same reader also wrote this (which I love:)


It’s tough out there but you can find happiness, as it starts with you. If you are upbeat, happy, and positive, you will have what you want. The partner is icing on the cake.

Please listen to him!! He is 100% right. So many men and women think happiness equates to finding a partner. While I’m not going to minimize the fact that being in a relationship is blissful (if it’s the right person), I agree that happiness in life equates with being happy alone—regardless of whether or not you are in a relationship. Happiness is achieved by doing things you love, enjoying little moments, and spending time with loved ones and friends. Happiness is about continual learning and growing as a person.


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People (including me) can think they have nothing else to learn in a specific area of their life and then they end up surprising themselves in a good way. Happiness is about loving yourself and being proud of who you are and what you do for others. It’s about appreciating things and people. It’s about loving those around you—not just in a romantic way, but loving your family, friends, strangers, nature, our country. It’s about spreading and receiving love and goodness.


I think when a person is really happy, when they are at peace with the past, and when they are really enjoying life is when they end up meeting someone significant.

I truly hope that happens for you! In the meantime, focus on YOU. Embrace your age and all of the wonderful things that come with being older. And please… stop worrying. Most things are out of your control.

Like this article? Check out, “Health, Wellness and Love Over 50”


You Deserve Beautiful, Healthy, Young Looking Skin


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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.

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