Is a Second Marriage An Opportunity For A Do-Over?

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May 25th, 2019 . Jackie Pilossoph

Look before you leap — into a second marriage by Jackie Pilossoph for Chicago Tribune Media Group If you got divorced, would you ever marry again? Almost every married person to whom I’ve asked this question has emphatically said no, for o...

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Second Marriage Over 50: Is It For You?

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

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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

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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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Should I Get Married? If You’re Even Asking, Then No!

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April 3rd, 2017 . Jackie Pilossoph

I love when people send me emails and ask, “Do you think I should get married?” I get so many of them! They say things like, “I’m not sure,” “I love him but I don’t think I’m IN LOVE with him,” “I’m afraid I will never find anyo...

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