Are You Dating A Playboy?

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

If you are dating a playboy or you aren’t sure, this is a great article for you. Published today in the Chicago Tribune Pioneer Press, this week’s Love Essentially is about playboys and why women either love them or why they run from them. Enjoy!

How Do Women Really Feel About Playboys? by Jackie Pilossoph for Chicago Tribune Pioneer Press

The sight of an old guy hanging out in satin pajamas, surrounded by three or four beautiful young women might have been disturbing to me, had it been anyone other than Hugh Hefner.


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In my eyes, Hefner, who died last week at the age of 91 seemed sort of sweet and harmless. Yes, the playboy who created Playboy was a sugar daddy who used his wealth, lifestyle and lavish parties to attract women a third of his age (or younger). But, he had charm, likability and a gentleness that made him seem like he couldn’t hurt a fly. In other words, I feel like Hefner was kind of a “nice” playboy.

But is there even such a thing? Aren’t playboys supposed to be wealthy, good-looking jerks, who date and sleep with multiple woman and refuse to commit to any kind of a meaningful relationship? If so, why would anyone want to date a playboy? (Click here to read the rest of the article, published in the Chicago Tribune Pioneer Press.)

Like this article? Check out my blog post, “49 Reasons To Be Inspired By Dating, Aging and Yes, Your Divorce”


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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:

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