Dating and Relationships

Are You Dating A Playboy?

Jackie Pilossoph
By Jackie PilossophFounder, Divorced Girl Smiling, Former Chicago Tribune Columnist and Features Reporter, Huffington Post Blogger and TV News Reporter

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
Jackie PilossophFounder, Divorced Girl Smiling, Former Chicago Tribune Columnist and Features Reporter, Huffington Post Blogger and TV News Reporter

Jackie Pilossoph, former Chicago Tribune Syndicated Columnist (LOVE ESSENTIALLY) is the Founder of DIVORCED GIRL SMILING. Divorced Girl Smiling (DGS), which is a well-known brand and community, offers a list of trusted, vetted divorce professionals, a podcast, articles and the free consult.

Pilossoph, who holds a Masters degree in Broadcast Journalism from Boston University, is a former television news reporter and features reporter for the Chicago Tribune. Her syndicated weekly column, LOVE ESSENTIALLY, was published in The Pioneer Press, The Chicago Tribune, and all Tribune Publishing editions, as well as Better magazine. Pilossoph was also a Huffington Post divorce blogger. Additionally, Pilossoph is the author of “Who Let the Dogs Out: An Empowering, Funny and Inspiring Guide to Dating After Divorce,” available everywhere books can be found.

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