Advice for Woman Dating a Divorced Man in His Forties

dating a divorced man in his forties

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

Dating a divorced man in his forties can be really, really tricky. Every divorced guy has his own unique story, and what he is going to be like in a relationship is based on that story, with countless factors that include: who wanted his divorce, his current relationship with his ex, his kids, his financial situation, his career, his emotional health, and what he’s looking for presently (a long-term relationship, a fun, casual relationship, a fling, etc.-or maybe he doesn’t even know!)


Here are just a few scenarios of dating a divorced man in his forties:



1. A guy is enthusiastic about jumping into a second marriage. I find this to be the case if his wife left him for another man and is now getting married. Like he has to keep up.


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2. On the opposite end of the spectrum, a guy is a player and just wants to sleep around, try to nail every woman out there. This could be an underlying subconscious decision based on anger, insecurity, or self-hatred.


3. A guy THINKS he wants a serious relationship, but really doesn’t because he is sabotaging every relationship he gets into. Either he finds something wrong with the woman, or refuses to commit to dozens of women, saying “she’s just not the one.”


4. A guy just wants to have fun and meet women, but isn’t ready to be tied down. But, this guy treats women with respect, doesn’t make promises, and is a good guy—just disappointing to a woman who wants something more serious than what he can offer.


5. The guy has no idea what he wants. He’s just still sort of shocked that he is single again and is just kind of drifting, swiping and seeing what happens with these women when they go out.


6. A guy is way too afraid to get into anything serious so he doesn’t date at all. Or, he can’t accept that his marriage is over and is still hoping the wife will come back.


7. The guy is the one who left. Maybe he left for another woman and it didn’t work out, so now he is looking for another relationship or just looking for hook-ups. Or, maybe he left without having someone else, and now just wants to meet someone nice—he’s looking for a healthy, happy, meaningful monogamous relationship.


8. A guy sees that there are many, many beautiful single women who are attracted to him. His wife never paid this much attention to him and he can’t believe it. He is pleasantly surprised, but then it goes to his head and he becomes a little bit over-confident, like he thinks he’s God’s gift to women.


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9. A guy rushes into things really really quickly. He’s saying I love you on the second date. He wants his happily ever after and will stop at nothing to make it happen quickly. He’s smothering.

10. A guy is hot and cold and sends mixed signals to the women he dates. Because he is so confused about what he wants, one minute he’s all in (acting like you’re the only person on the planet), the next he’s looking around the room at other women. One day he texts 50 times, then you don’t hear from him for days.


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I want to address #10, based on this email I received from a woman dating a divorced man in his forties and seeking advice:


Had a very difficult week with my divorced boyfriend– he seemed to be distancing himself after a fantastic, but slow-building few months. We spoke on the phone yesterday and he confessed that he was concerned his “heart would never open again” and he didn’t want to lead me on, yet then said that he feels we have a connection he hardly ever feels, he loves spending time with me and feels he should open up more and tell me about the divorce itself – extremely confusing/mixed messages! I told him I’m in absolutely no hurry and I’m completely happy with the way things are and he seemed to accept this and we came off the phone happy, however it’s been whirling round in my head ever since.


Of course it’s whirling around in her head. The whirling is legit. This guy is very very confused. I am saying this based on YEARS, maybe decades of dating experience. If you feel like someone you are dating is distancing himself from you, HE IS. Don’t listen to your girlfriends who say, “Maybe he’s just busy.” “Maybe he just needs some space.” No. He is having doubts about you, for one of only two reasons: 1. He’s just not that into you. (yes, I am stealing this line from the bestselling book.) or 2. He is very confused and needs therapy. I am not saying that in a sarcastic way. He genuinely needs help, which is understandable! Divorce is traumatizing and one of the most difficult things a person can go through. Of course you need help.


I think she handled this great—telling him that she is in no hurry and is completely happy. But, I have to say, I think she is lying to herself. If she senses the distancing, it bothers her. Otherwise, she wouldn’t care if he was distant and she wouldn’t have taken the time to reach out to me.


In my opinion, she has every right to feel disappointed and frustrated by this guy’s conflicted feelings. He is taking her on his rollercoaster ride. Bringing her down: “My heart will never open again, I don’t want to lead you on.” Only to give her hope: “We have a connection I hardly ever feel,” “I love spending time with you,” “I should tell you about my divorce.” Come on! Is this fair? Not at all. This woman deserves a guy who is committed. By committed, I don’t mean that he should know right this minute if she’s the one, but rather, committed to giving the relationship a fair shot by really getting to know her.


All that said, he can’t help his fears, and he isn’t doing it to hurt her. He’s a damaged divorced guy, and I don’t say “damaged” with judgement. I, myself am damaged. Everyone I know who is divorced is damaged, and actually, so are people who are happily married, in some ways.


I think this woman should continue dating this guy, but should keep an open mind with other men, date other men, and try not to get her hopes up about this guy. Things could turn around, but I tend to find that most times, when someone gets mixed feelings, it doesn’t usually end well. I hate to say that. I hope I’m wrong. But this divorced guy is conflicted. Maybe over time he will change, and be able to give this woman (or his next girlfriend) less mixed messages and more of the best of him. I hope so.

Like this article? Check out, “There are no Buts in a Happy Healthy Romantic Relationship”


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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:

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