What Are “The Rules” When You Start Dating Again After Divorce?

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

This was posted on a the DGS group Facebook page: When you start dating again after divorce, what are the rules? I have no idea what the new normal is!


Her question made me think. Remember the self-help book “The Rules?” Officially titled, “The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right,” the book came out in 1995. I was 30 at the time, unmarried, and definitely frustrated when it came to meeting the right person. I read The Rules that year and loved it. In my opinion, authors, Ellen Fein and Sherrie Schneider were right on in their philosophy that a woman should let a man pursue her and not the other way around.


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Some might think The Rules is old-fashioned and antifeminist. I’m actually OK with it. I think these days, it’s pretty common for some woman to chase a guy who just isn’t that interested, especially in dating again after divorce.


I’m not judging anyone who does this because I have done it myself (when I was younger), but what I’m saying is, I think so many women have really lowered their standards in the way they are willing to let a man treat them. I think they do this for a few reasons:


1. It’s hard to meet people, so when they meet someone they like, they are hoping to morph the person into Mr. Right.

2. People have loneliness. It’s better to be treated badly than to be alone for certain people.


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3. They think they can’t do better. Self-esteem can be lower after divorce and/or as people age.

4. It’s easier to convince themselves that the guy will change all of a sudden. They have false hopes because it’s too painful to face the truth.

Again, I’m not judging. I have been there. In the past, I have let dates/boyfriends treat me badly and I stayed in the relationship. It’s very hard to be honest with yourself. I get it. But letting someone treat you in a way you don’t think is good enough is toxic to self-esteem, self-confidence and self-love.


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So, what are the rules when people start dating again after divorce? Here are MY rules—the way I think women should be treated.


1. If a guy doesn’t text you after a date, I see red flags.

That said, if you feel like you want to text to thank him for dinner, I think a short, kind text is appropriate. But after that, he needs to take the lead and start texting or calling.

2. No sex on a first date.

3. Let him take the lead in how often you are texting/talking/seeing each other.

Maintain your social life and don’t cancel plans for him. He will wait for you.

4. Don’t introduce kids to him for at least 3 months.

And, I wouldn’t introduce anyone to my kids who I didn’t think was going to be significant in my life. They are going through a lot. They might be insecure about spending time with you. They are already going through a lot of change and Mom having a boyfriend is another big one. Better to be a little selfless right now and wait.


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5. Just because he wants you to meet his kids, don’t feel obligated to introduce him to yours.

6. If he cancels a date because of his kids, it’s perfectly understandable.

Even last minute cancellations are acceptable in dating after divorce, but only if it is kid related.

7. If you have to cancel a date because of your kids, it’s perfectly understandable.

If he’s upset, and if he makes a big deal out of it, he’s not for you.



8. If he is moving really fast, saying the L word quickly, wanting to be with you every second, that’s wonderful, but might be a red flag.

Is he crazy in love or does he have an inability to be alone? It’s a valid question. I remember this one guy trying to get serious with me really quickly and looking back, I think it was because his wife was getting remarried and he was in a competition with her.


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9. If he cheats, even one time, there are no second chances.

Remember, you deserve only the best. This is not even up for discussion!

10. Don’t settle.

What I mean by that is, if in your heart, you know he’s not treating you the way you deserve, break up. Let yourself be OK with being alone for awhile. You will love yourself for it. You will admire yourself for it. And, you will thank yourself when Mr. Wonderful (Mr. Right) comes along.

11. Love love love love love him.

He’s most likely divorced too, so he’s been hurt. Don’t be afraid to be vulnerable and to show him love. He will love you back if he knows you are all in. And if he doesn’t, he’s not the one.


I know these rules in dating again after divorce sound harsh, and I might sound like a know-it-all. I’m not, but I do have experience with being in both dysfunctional and wonderful relationships. Perhaps I failed to tell you the biggest rule in dating again after divorce, which is to love yourself. And if you love yourself, you know that you owe it to yourself to follow all these other rules.

Like this article? Check out, “Naked and Terrified: Why There’s No Need To Fear Sex After Divorce”


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    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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