20 Lies We Tell Ourselves in Dating after Divorce


December 6th, 2021 . Jackie Pilossoph

Let’s be honest. Datingafter divorce isn't easy. It's sort of like a roller coaster. Great dates make us giddy and hopeful and inspired, but a string of bad dates can cause frustration, along with feelings of hopelessness and that awful question, ...

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Do Looks Matter More than Personality? They Shouldn’t.


November 30th, 2021 . Jackie Pilossoph

When it comes to dating after divorce, something that bugs me immensely (and both men and women are guilty of it) are that people think looks are the most important thing. Do looks matter more than personality? To some, yes. Do looks matter more than...

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Dating After Divorce At 50: What To Wear, What To Say And Other Tips


November 8th, 2021 . Jackie Pilossoph

When I was 49 years old, I ended a six year relationship. Single again at 49 and dating again was nauseating to think about, but I did it. Is dating after divorce at 50 easy? Um... How can I say this delicately? HELL NO. That said, there are ma...

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I Feel Broken: Dumped, Angry And In Pain


October 29th, 2021 . Jackie Pilossoph

I’ve been corresponding with a reader who has been divorced for several years, and was recently in a relationship for well over a year, which she thought was happy, healthy, and loving. Until her boyfriend broke up with her via text, causing to wri...

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Are You Dating A Player Or Is He Just A Player With You?


October 23rd, 2021 . Jackie Pilossoph

This is a great dating story about a divorced friend of mine who was dating a player (or so I thought.)   It all started last fall, when she went out with a guy she really thought she liked. The problem was, he wasn’t treating her very w...

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