7 Men To Avoid When Dating Post-Divorce

dating post-divorce

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

Picture this scenario: You’re feeling great now that the divorce is behind you. The kids are doing better, you’re feeling more financially confident, the devastation of your split is becoming a distant memory, and—surprisingly, dating post-divorce isn’t as bad as you imagined. You finally meet a guy you like.

Then the shoe drops. You realize this dating post-divorce thing might be harder than you thought. You find out you’re not the only woman your new guy is dating, and suddenly you realize you shouldn’t have ignored the red flags you saw when he was getting all those late-night texts.

More heartbreak in dating post-divorce is the last thing a divorced single mom needs. If you’re not careful in the men you choose to date, you could get hurt.

Here are seven types of men to avoid dating post-divorce:


    1. The drinker.

Excessive drinking can lead to bad things. DUIs, alcoholism, cheating, and other bad behavior are just some possible outcomes of overindulging in alcohol.

So if he’s ordering three or four drinks every time you go out for dinner or if all your dates involve alcohol, consider the fact that there may be a drinking issue, so it’s important to pay attention to it. I also realize that when men and women are newly divorced and on first dates, they might drink more alcohol than they normally do to ease nervousness. Still, don’t let the infatuation you feel toward him mask a problem that might end up being significant.


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2. The narcissist.

Narcissistic personality disorder can include an excessive need for admiration, the failure to recognize other people’s feelings, the inability to handle criticism of any kind, the need to control you, and a sense of entitlement. Know anyone like that? A person like this can be very difficult to be around and can really hurt your self-esteem, which is why you want to stay away from him.

3.  The womanizer.

I find that some older, divorced men turn into womanizers, a result of possibly not wanting to commit again for fear of getting hurt. They are pretty easy to spot, and you will know within a few dates if your guy is seeing other women. You might be OK with that, but don’t try to talk yourself into accepting a situation you don’t want to be in because either you think he will change or you are settling. I believe that dating someone who is dating other women (when you want to be monogamous) leads to low self-esteem, disappointment, and unhappiness.


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4.  The angry, bitter guy.

In dating post-divorce, this guy is toxic to be around. You don’t deserve to have to deal with someone’s divorce baggage—you have your own. An angry, bitter guy will complain about his situation, bad-mouth his ex, and focus on how unfair life is. Stay away. Spending a lot of time with someone like this is exhausting and depressing. Encourage him to go to counseling and then be done.



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5.  The gambler.

The National Council on Problem Gambling reported that 15% of Americans gamble at least once a week, and six million adults meet the criteria for problem gambling. I’m not saying all men who bet on sports are gambling addicts, but be wise enough to know the difference between someone who is just having fun and someone who has a gambling addiction. If you end up in a long-term relationship with him, it could be detrimental, not only emotionally but also financially.

6.  The pothead/druggie.

Much like the gambler, this guy could have an addiction that affects you greatly. Have the wisdom to recognize it and the courage to separate yourself from him if your gut tells you there is an issue.

7.  The rebound guy.

Perhaps the most difficult to admit to yourself, the rebound guy isn’t over his ex. He is constantly talking about her, and you have a suspicion that he is using you to help break away from his feelings. I have been the rebound guy’s girl before, and trust me: it isn’t easy.


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When it ends, you feel used, even though he didn’t intend to make you feel that way. Be cautious. Don’t allow your new relationship partner to set the pace. If you do, you will find yourself in the middle of a whirlwind. You don’t want to be left in the dust once he decides to move on.

The rebound guy is usually a good guy. He just needs a little bit of time before he is capable of being in a healthy, romantic relationship. If you end up dating one of these guys, consider it bad timing and bad luck, and never, ever take it personally.


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In closing, there are so many wonderful divorced men out there who aren’t addicts, womanizers, narcissists, or angry and bitter. It might take time, and you might have to go on a lot of dates before meeting that special guy who feels like the right match, but when you meet him, he will have been worth waiting for. In the meantime, be smart by doing your best to stay away from these seven types of guys.

Like this article? Check out my blog, “There are no buts in a 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: DivorcedGirlSmiling.com

    3 Responses to “7 Men To Avoid When Dating Post-Divorce”

    1. Barry S. Resnick

      The Narcissist is the most dangerous one to date….add emotion, alcohol, lies and usury and you have a deadly cocktail. Before I married my wonderful wife (who is awesome and my best friend), I dated a crazy drunk narcissist who I actually knew from high school and became reacquainted at age 47…what a trip this was and it was a very educational experience. The one very sickening aspect of this type of personality is NO INTEGRITY for anything. I do not drink alcohol at all and never did I ever have a drink with her, but she had no problem drinking to excess around me. I have watched her drink a twelve pack within a two hour period…I walked away after the lying, staying out all night and sleeping around and worst of all, used an old man for his money. Front row seat to a real freak show.

    2. Sean Gartland

      Love the article, but these are certainly not unique to men! I met and dated all of these people and more, except they were women! Some additional characters in my dating misadventures included: The Man Hater, The Man Eater, Daddy’s Girl, The 40 Something Teenager, The Gold Digger, and The “Bad Girl” aka “Biker Chick”. All turned out to be bad news and women to avoid!

    3. Dor

      How about the 70 plus older widowed man who is a player and uses women?
      I met him and felt used.
      He was fun, charming and loved drama.
      Watch out for this one.


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