Dating a 40 Year Old Man Who has Never Married

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What’s the opposite of a divorced man? If you answered “a married man” you’re wrong. When it comes to dating, the opposite of a divorced man is a guy who has never been married! Dating a 40 year old man who has never been married is interesting. I did it. Here’s my story.

One night, several years ago, I was out with a male friend of mine. The plan was to have a quick drink–one hour, catch up and go home. Not surprisingly, in the world of men and women dating after divorce, you never know how the night will turn out.

So, after about 20 minutes, this absolutely gorgeous man walks into the bar where we were. Mind you, this was a suburban bar, so the chances of someone like this walking in–someone who no one knew was slim.


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I turned to my friend and said, “That guy looks exactly like Denzel Washington.” So, my friend, without hesitation, says very loudly to the guy, “She thinks you look like Denzel Washington!” I wanted to crawl under the bar.

But, I didn’t. Instead, Denzel (I’ll just call him that) asked if he could join us for a drink and the three of us talked for a couple hours. Turns out, Denzel was a 40 year old man, never married, who had just moved to our suburb for a job. A former college football star turned corporate executive, this guy was absolutely one of the most attractive men (and the sweetest) I have ever met.

Around 11:30pm, the three of us headed to a dive bar where it was karaoke night. Keep in mind this was a Tuesday night. We sang and danced and talked until 2am and I was very smitten with this tall, dark and handsome man.

All that said, I learned a lot. He kept texting someone, and seemed a little bit like a player. I just got that vibe. It was a little bit of a red flag, so I noticed it but tried not to judge. I learned that Denzel had grown up in a small town and played college football, and for almost 20 years, had a lucrative career in a large company in the food and beverage industry.


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He ended up asking for my number and the next day, came with me to an exercise class with all women. To watch him doing lunges and squats and weight lifting (with her perfectly cut body) was so funny, but what was even funnier, was seeing all the women drooling over him. The next night, Denzel took me to dinner.

Dating a 40 year old man who has never been married…

The date could not have gone better. Denzel was a total gentleman and I had such a lovely time. You could just tell he was a good person. He didn’t even look at his phone the entire date. Our conversation included my writing career, in which Denzel made a few very good suggestions, my kids, his childhood, and more. We kissed at the end of the night and it was perfect.

I’ve made some really bad decisions in my life, and one of them was getting back together with a man I had been seeing before I met Denzel. So, I had to tell Denzel I couldn’t see him anymore. He ended up moving out of town and I ended up breaking up with the other guy. I guess it wasn’t meant to be. I still have THE BEST memories of Denzel and I hope he is happily in a relationship (or married) if that’s what he wants.


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Denzel taught me a lot about dating a 40 year old man who has never been married.

Here are some things to consider if you are divorced and you date someone who has never been married:


1.     Kids.

Someone who is divorced (depending on his age) most likely has kids, which means he will feel a little bit more comfortable with your kids. Remember, there are some guys who have never been married who have kids, and there are some guys who have never been married but have dated a lot of women with kids, so they might be used to being around kids.

There are also divorced guys who have never had kids. Here’s the thing. I find that a divorced guy, who has his own kids has a certain ease around children. If you are dating someone who hasn’t been around kids much, they might not enjoy it. It might be awkward at first. Or, it might turn out great. I have a feeling it would have been wonderful with Denzel. The guy might end up really hitting it off with your kids. Or, he might fall madly in love with your kids and realize they want more. Yikes! That could be an issue for some people.


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2.    The ability to be domestic, in other words, can he play house?

Let’s face it. Once you’ve been married, you’ve seen it all. Nakedness in broad daylight, those annoying habits, likes clothes all over the floor, the burping you never experience when you’re dating, and really the way the person lives. Can a guy who has never been married handle this? Maybe, maybe not. Maybe he’s lived with someone. Or, maybe he’ll run for the hills the first time he sees you sitting on the bathtub ledge clipping your toenails.  Then again, maybe I’m not giving the 40 year old man who has never been married enough credit. Maybe true love can overcome all those things.


 3.    Baggage.

Here’s a plus for the guy who has never been married. He’s carrying way less baggage than the divorced guy. He’s not bashing his ex every three days, he’s not saying good-bye to his kids and then having that sad look on his face, and he doesn’t have that wounded look that says, “My wife ruined my life.” The man who has never been married is fresh, untainted. Although, how do I know he wasn’t madly in love and then dumped? Is his breakup any less significant because he wasn’t legally married? I admit, everyone has baggage. But, the divorced man’s baggage is a little heavier, given kids, legal issues, assets, finances, and more.


4. Commitment.

There’s commitment and then there’s commitment. The divorced guy committed. He stood in front of God or a judge and a crowd of people and agreed to commit in writing. A man who has never been married could have a commitment issue. Again, I’m not bashing Denzel or any other man who has never been married. I don’t know the story.

He could have always wanted to commit and just never found the right person. Or, maybe he committed (got engaged) and then the girl broke it off. Who knows. All I’m saying is, the divorced guy proved he had the ability and the willingness to complete and utter monogamy (Then again, he could have been a huge cheater in the marriage.) Plus, maybe he never wants to commit again.


Rita Morris, Certified Life Coach and Parenting Coach


Both a divorced man and a man who has never been married can be amazing guys. They can also both be jerks. In other words, I’m not saying one is better than the other. But the bottom line is, try not to define someone based on whether or not they have ever been married.

Everyone has a different story, and a reason why they ended up divorced or never married. Maybe it’s choice, maybe it’s bad luck (or good luck) and maybe it shouldn’t even be factored into the relationship. In other words, maybe it doesn’t even matter.


What does matter? The individual person. Is he going to love you unconditionally? Will he be here for you if you really need him? Can you trust him? Will he always make your heart pound when he walks into a room? Those are a lot more important questions than “Has he ever been married?” don’t you think?


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers.

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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