Second Marriage Over 50: Is It For You?


January 29th, 2018 . Jackie Pilossoph

Recently, four couples, including myself and my boyfriend, met at a bar to have some drinks. Of the eight people who were there, all are divorced with kids, and seven out of the eight are over 50. None are in a second marriage.   Here is w...

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Divorce Advice: Here’s What Happens When You Move On Too Fast


January 2nd, 2018 . Jackie Pilossoph

  This reader is seeking divorce advice: I have been divorced for two years (no kids), and I have since gotten remarried to an amazing lady and we have a child together.  You would think all of the emotion would be gone regarding my first...

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What Was This Guy Thinking Getting Engaged In Front Of His Kids?


November 2nd, 2017 . Jackie Pilossoph

There are so many romantic ways to get engaged: on a boat, in a park, at a romantic dinner, on vacation, or my favorite-- in the place where you met or fell in love. Getting engaged is such a beautiful occasion, and something that the couple will rem...

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Considering A Second Marriage? Let’s Talk About The Wedding


September 23rd, 2017 . Jackie Pilossoph

Those considering second marriage might benefit from reading my Love Essentially column, published in the Chicago Tribune Pioneer Press. When it comes to the actual wedding, there are big differences from a first wedding. Here are my thoughts on a re...

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A Great Strategy For Blending Families


August 27th, 2017 . Jackie Pilossoph

I received this email from a divorced dad seeking advice about blending families:   I'm a divorced dad of two teenage boys and have been divorced for over 12 years. I've dated many women over the last decade and haven't connected with "the...

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