Dating after Divorce: Choosing Bad Isn’t Bad Luck

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

You’re on cloud nine. You thought dating after divorce was going to be a nightmare, but you were wrong! You found a great guy who you adore. He’s handsome, sensitive, kind, funny, athletic, attentive, charming, great with your kids, and in bed, he’s rocking your world. He’s even talking marriage!

Then, the shoe drops. You find out he’s been cheating. Not just once. A lot. You’re shocked. But not really.

You look back at things you didn’t let yourself see. The random text he got at 2:13 a.m., the time he was unaccountable for 2 days, a friend telling you she swears she saw him out one night with another woman. The signs were there, but you ignored them because you just wanted to be happy. After all, you deserve to be happy after going through hell with your divorce, right?

Right. That’s why I decided to write this blog. You might not want to hear this, but a scenario like this isn’t bad luck, it’s YOU choosing badly.

I was recently talking to a woman who has been divorced for almost 10 years. She was dating a man for 3 years, and thought everything was perfect, until she found out he had cheated with multiple women. She’s heartbroken.

“I think I should go to therapy and find out why I chose someone like this,” she said to me.

Here’s the thing. Even though this woman’s marriage ended in divorce, she will be the first one to tell you that he’s a good guy, but that they just drifted apart with age. In other words, she chose well. He didn’t cheat and is a great dad.

The woman also seems really stable and put together, very beautiful and successful professionally, and a great mom. The fact that she made the statement that she wants to explore why she chose a cheater is really healthy.

In my opinion, I bet this woman will choose great next time around. But there are others who choose badly often or ALWAYS. I am someone who has made bad choices in men in my life. So, I’m not judging anyone.

But I want to try to help, because I think that when we understand why we are choosing badly, we can avoid making those mistakes over and over again.

So, first of all, what does “choosing badly” mean? A drug addict, an alcoholic, a pothead, a control-freak, a cheater, a physical or mental abuser.

By the way, I also want to add that I’m not just talking about women choosing bad men. Men can choose badly too. Women can be alcoholics and drug addicts and abusers and cheaters, too.

Here are the reasons I think people choose badly:

1. Fear of being alone: I can’t even count the number of men and women who get divorced and are married two minutes later. Call me judgmental, but I just don’t get it. Why not take the time (I’m saying years) to get to know someone? I have to believe that the chances of breaking up keep going down as the years go on. Although, nothing is a guarantee. But, I’d hate to marry someone, and two years later, be sitting there saying, “What the heck did I do?” What’s wrong with taking a few years to be by yourself? I’m not saying sit home alone. Date, fall in love, be as romantic and committed as you can be. When I say “be by yourself,” I just mean don’t rush to the altar again so quickly.

2. Trying to compete with the ex: I’ve seen this a lot too. One of the people gets remarried quickly, so the other one rushes into something with the wrong person, trying to prove to the world that they are happy too. It’s really sad to me.

3. Low self-esteem and lack of self-love: This is the biggest reason people choose badly. People are willing to put up with things like excessive drinking, abusive behavior and cheating because they don’t feel like they deserve any better for a few possible reasons. First, they might not have the confidence to realize how unacceptable the behavior really is. It might stem from childhood. Maybe their mother let their father treat them this way and so it seems acceptable. Or, it might stem from the insecurity of the circumstances of their divorce. Maybe the wife leaving left the guy with such little self esteem that he’ll take anyone who loves him, no matter what she’s like. Or, it could be the fact that the person has no professional life or passion or hobby, so they have no self worth.  Lastly, it could be that they simply don’t like who they are. I’ve seen absolutely drop-dead gorgeous women and men who have zero self-love. Really successful people, too! Ask my friend, author and life coach, Sylvia Friedman. She will tell you about all the men and women who lack self love and how it affects their lives for the worse.

The thing is, no guy or girl is perfect. I’m not saying to go out and settle for nothing less than Prince Charming. But NO ONE, man or woman deserves to be with someone who cheats, abuses them physically or mentally, or who is out of control with drugs or alcohol.

Dating advice: Let yourself see the red flags. If he has four beers in the first half hour, I’m not saying he’s an alcoholic, I’m saying, be aware of it. If he’s getting texts and phone calls late at night, be aware of it. If he has a little too much to drink and pushes you against the wall, do you really feel like it’s something you should let slide? It’s up to you, but I hope you take a good look in the mirror and discover all your wonderful qualities, and don’t let someone treat you improperly.


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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.

2 Responses to “Dating after Divorce: Choosing Bad Isn’t Bad Luck”

  1. Sue

    Hi Jackie,
    Thank you for one of the best blog divorce sites! I have recently got divorced and your site has really kept me going. Have also forwarded into a few friends. A lot of your stories have really hit home, and have been truly helpful.


  2. Laura

    Just found your blog and I am so happy I did. Very informative. I totally relate as I’ve been divorced for 6 years.
    I will continue to follow your blog!
    Visit us at



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