Relationship Advice: The Do’s & Don’ts of saying “I Love You”


May 22nd, 2014 . Jackie Pilossoph

  Those three little words that we all long to hear from the man or woman we adore can mean the world, but if said at an inopportune time or under the wrong circumstances, “I love you” can be a dreaded statement that might cause confusion...

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Dating Advice: 20 Lies People Tell Themselves When it Comes to Dating


May 15th, 2014 . Jackie Pilossoph

  The Divorced Girl Smiling is REALLY smiling today, as my new column in Sun-Times local launched today! It's a  weekly relationship and dating advice column called "Love Essentially." Here is the first column, 20 Lies People Tell Themse...

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First Date Tips: Good And Bad Topics of Conversation


April 14th, 2014 . Jackie Pilossoph

Although they can be hopeful, exciting and fun, let's be honest. First dates can consist of moments of awkward silence, feeling like you have food between your teeth, wondering if he noticed your nervousness, thinking you said something really stupid...

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Dating Someone Who is Not Divorced Yet: Is it Right For You?


March 14th, 2014 . Jackie Pilossoph

There are many men and women who have a rule when it comes to dating someone who is not divorced yet: they won’t do it. A few years ago, I tried to set up a guy who was separated but not divorced yet with a divorced woman. When I told the woman he ...

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Man Up! Here’s What Women Want In Dating


March 11th, 2014 . Jackie Pilossoph

It’s no big secret that dating after divorce is challenging, and that meeting someone doesn’t come easily. But I really believe every dog has his day, meaning eventually, every divorced person (the same ones who say “I’m never going to meet a...

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