Are You Dating A Playboy?

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

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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    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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