Baggage is OK! The Benefits of Dating Someone Who Is Divorced


October 1st, 2019 . Jackie Pilossoph

Dating someone who is divorced is complicated. Very complicated. You've got an ex in the picture, you've got his ex, you've got the kids, you've got his kids, you've got lifestyle changes, you've got financial issues and child support payments... ...

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Advice For: “I Got Divorced Because I Cheated. How Do I Tell My New Girlfriend?”


August 18th, 2016 . Jackie Pilossoph

Advice for: "I got divorced because I cheated. How do I tell my new girlfriend?" I have a guy friend who got divorced a few years ago. I have seen him go through immense remorse for having an affair while he was married, and guilt that was so inte...

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Why Your Divorce Might Be Directly Linked To Your Childhood


June 20th, 2016 . Jackie Pilossoph

Things become so much more clear after the dust settles, right? When reflecting on your divorce, you might want to examine why you chose to be in a relationship that didn't work. This will help you choose the right person in future relationships. Tha...

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Relationship Closure: Do We Need It or Is It Better To Let Things Go?


October 16th, 2015 . Jackie Pilossoph

When it comes to breakups, are you one of those people who needs relationship closure in order to move on? Or is a clean break your style?  In this week's Love Essentially column, published yesterday in Chicago Tribune Pioneer Press, I offer the...

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Let’s Talk About Sex After Divorce–Safe Sex, That Is


June 29th, 2014 . Jackie Pilossoph

Divorced Girl Smiling received this e-mail from a reader seeking advice about sex after divorce and how to be safe. I went out with a guy a couple of times and we really hit it off. Our relationship quickly became physical and in the heat of the m...

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