Dating a 40 Year Old Man Who has Never Been Married: My Story

dating a 40 year old man who has never been married

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

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.


Colleen Breems, Divorce Attorney, Beermann, LLP


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.


Varghese Summersett



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 are dating a 40 year old man who has never been married–or any man 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.


Cherie Morris, J.D. - Divorce Coach and
Founder, Dear Divorce 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?

Like this article? Check out, “Dating someone who is hot and cold”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    14 Responses to “Dating a 40 Year Old Man Who has Never Been Married: My Story”

    1. Page

      I’m in the “other” category. I happen to be a divorced woman that never had kids nor will I ever be able to have my own. My situation is uncommon I think.

    2. Aurelia

      I’m a fairly new single mother of one child who I had out of wedlock. However, I still feel like I could easily fall in the “divorced” category, regardless of the fact that I was not LEGALLY bound to my ex. Upon separation, I still went through ALL of the emotions, ALL of the custody battles, and ALL of the money issues that your typical divorcee goes through.

      And because of this, when I get ready to date again, I would definitely prefer a man who can also fall in the same “divorced” category as me. We’d be able to understand each other so much better, and understand the pain that will never completely go away. This is something that never-been-married people just won’t understand. They look at our situations as just-get-over-it problems, when that couldn’t be farther from the truth.

      I’ve had to make this decision in order to help heal my heart and move forward with my life. I’m so glad you posted this! It’s blog posts like these that remind me of how far I’ve really come as a single mom!

      xoxo, Aurelia

    3. Linda

      He had never married. During our marriage, he never got it. He was a momma’s boy and I left him after two years. Don’t marry a momma’s boy. It doesn’t work. He preferred visiting his mother’s grave rather than visit with my adult daughter and her fiancée, she a combat veteran, college graduate, two weeks before their wedding. That’s when I knew I was done. He was unable to accept family and joy.

    4. Singles Warehouse

      “I wish they had a checkbox for the things that really mean the most, like, “Are you going to love me unconditionally?” “Will you be here for me if I really need you?” and “Will you always cause my heart to beat fast when you walk into a room?” That’s more important than his past marital status, don’t you think?”

      Jackie – I couldn’t agree more. I have a friend who’s just started dating someone with kids from a past relationship. They spent some time with me on my birthday and he was so worried about what people would think…

      Here’s what I think – I just want them to be happy. Simple

    5. Sesimie

      Interesting read….I’ve been that non-married guy and then i got married….now i’m the divorced guy,

      I was so naive before …..but indeed living with someone for years becomes habit. Even now i sleep on one side of my bed automatically leaving space for her and chuckling to myself when i finally “stretch” out.

      Non married guys need to be willing to share everything…..the Good, the Bad…and yup the Ugly. You Think you know someone until that first trip to the pharmacy for feminine hygiene products…..or the first time you really do groceries for two.

      You need to live with them, travel with them, see how they are around families….I’m actually pretty glad I’ve experienced Marriage for years and also was able to amicably divorce.

      As a divorcé i’m approached with hesitation by many women who are not really interested in me….but the divorce 🙂
      Divorced women are different……because they know i know how the real woman is at home. They know that we share a hurt…a pain and thus we can converse.

      Yup it was a good read TY.

    6. Eva

      I’d been on the post-divorce dating circuit long enough to know that I would now never date a man who hasn’t had kids. Being a parent doesn’t make you a better person, but it surely makes you a different one, the differences are striking enough that I could not date a childless man. As a parent, your own self-actualization and happiness suddenly takes a backseat to your child’s self-actualization and happiness, and a parent WILLINGLY makes this sacrifice. For example, if the choice were to fulfill my dream of travelling around the world, or use that money to support my child’s dream of opening a restaurant, I would WILLINGLY sacrifice my dream for his… because I’m his mom. I speak only for myself, but people I know who are childless “get it” intellectually, but not at deeper levels. Yes, tehre are people with children who don’t “get it” as well, but having children increases the odds that they understand.

    7. Barbara

      When I got divorced, I was surprised at how immature guys who had never been married were. I could not tolerate it and found I had more in common with divorced men. They are mature, they recognize what it takes to make or break a relationship and they take commitments seriously because they know what it is like to go through the stress of a formal break-up (divorce).

    8. PJay

      Men should stay single and play the field. Women are a nightmare in this country – legally privileged, socially pampered and economically favored.

      • Alski

        The tides are turning, my friend. They fight for equality and will get the other edge of the sword. The days of legal privilege are numbered. They now pay alimony and child support in many more cases, let’s see them treat us like shit when they start to get the same consequences as men.

        But I agree,men, play the field for the rest of your life.

    9. neveragain

      I have been seperated now for 7 years. I have dated both men who have kids and are divorced, men who are divorced with no kids and also men who have never been married without kids. I would have to say that because I have kids its easiest with the guys who have kids. They just get it. If I have to cancel on short notice because my kids are sick, they don’t complain. I will not date a man who doesn’t have kids again. And the guy who was almost 50 and no long term relationship experience……lets just say….wow, there are some serious issues there.

    10. Carlos

      Reading this after dating a divorced women and eventually seeing her end up with the divorced older guy she was seeing before she meet me. Makes me better understand why she did end up with him, even do he had more baggage. I can’t say I wasn’t or am ready for a commitment, but I did see that a women who has been married before, she looks for other things that at least I as a never before married guy have not experienced going threw hardship since the only person I have had to take care off has been mostly me. And this particular women basically from day 1 up until the very end, always seemed to have things happen in her life, if it wasn’t a friend having her new born die, family problems, domestic issues with her sister, car problems, money problems, etc… It was just to much for me to every time have the right action needed or support she needed from me, and of course I have not really have had money issues in a very long time, so allot of this stuff was knew and a men who has been their and done that, ended up with a very good women. Going threw this experience and reading this article has opened my eyes to what I will have to expect going forward, not everyone has it as easy as I do and financial stability is not what’s going to get the job done at the end, allot of other things are just as important to a women, specially one who has been married before and knows what issues come up in a marriage or living together situation.

    11. Alski

      This article is ridiculous. For example, “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.) ”

      You’re all over the place! Is this how women think/rationalize? Jeeezus. What’s the point? Who’s side are you on?

    12. Dor

      If you’re divorced and seeing a divorce guy , obviously you both have that in common.
      Men who are in their 50’s plus and have never been married is a bit odd.
      Maybe a player or didn’t want to commit.


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