Second Marriage: Should You Take That Chance?


October 22nd, 2015 . Jackie Pilossoph

I am a huge fan of second marriage, and I love love love hearing those happy stories. That said, I think I read somewhere that 72% of second marriages end in divorce, which makes me sad. If someone asked me what the key is to ending up in the 2...

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Which is Worse? Ending a Marriage Or Ending a Serious Relationship


September 15th, 2014 . Jackie Pilossoph

Ending a marriage is never easy. In fact, it’s one of the most difficult things I have ever been through in my life. But, if you can believe it, I think that ending a serious relationship could be even more painful. Hear me out before you say, "...

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Why Rushing Into Relationships Might be a Bad Idea


July 31st, 2014 . Jackie Pilossoph

In my Love Essentially column that came out today in Sun-Times Media Local, I talk about reasons why men and women rush into relationships, and why rushing into relationships isn't always wise. What baffles my mind, even more than single people rus...

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It’s Complicated! Relationship Advice for A Divorced Woman


June 12th, 2014 . Jackie Pilossoph

The Sun-Times received this letter from a divorced woman asking for relationship advice. Jackie, I am at a point in my life where I am questioning my relationship. I feel like it could be several things, such as not feeling like I have forg...

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Should I Move In With My Boyfriend?


June 11th, 2014 . Jackie Pilossoph

Should I move in with my boyfriend? It's a question that girlfriends ask girlfriends, but even more so, ask themselves, especially if they are divorced and have kids.  Remember the movie, "About Last Night?", (not the remake, the original), speci...

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