Newly Separated Man Seeks Custody Advice


April 1st, 2022 . Jackie Pilossoph

Divorced Girl Smiling received a heartbreaking e-mail from a newly separated man seeking custody advice. His two young children are having difficulty transitioning from one house to another.  Dear Jackie, Earlier this year my wife of 9 years l...

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Experiencing True Gratitude Means Getting Rid of “It Could Always Be Worse” Attitude


November 24th, 2016 . Jackie Pilossoph

        I hate when people say, "It could always be worse." Like we should be grateful our horrible situation is what it is and not worse. For example, you get separated because your spouse was cheating and people ...

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Divorced Dad Dating: The Challenges One Dad Said He’s Facing


October 28th, 2016 . Jackie Pilossoph

          This email came from a 42 year-old divorced dad dating who shares custody of his 10 year-old daughter. I thought it was interesting how he categorized his dating challenges according to the ages o...

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The Sex Appeal of The Single Dad


June 19th, 2016 . Jackie Pilossoph

I thought Father’s Day was the perfect day to respond to this e-mail I received from a single dad, who seems like he’s lacking self-confidence when it comes to dating.   I recently read one of your posts, "Single Dad Dating: "Are My Ki...

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Newly Separated Guy With 4 Kids: Will Women Want To Date Him?


April 27th, 2016 . Jackie Pilossoph

      I am a newly separated man heading to divorce as she has been cheating. I have four children whom I love dearly and spend a significant amount of time with. There isn’t a strong market for divorced 43 year old men ...

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Divorce Support for Men (In The Form of a Play)


November 4th, 2015 . Jackie Pilossoph

It's an interesting way to offer divorce support for men, but playwright, John N. Frank is doing it in his new production, "Boys In The Basement." Here is Frank's guest post about his Evanston based play, that he hopes will help both men and women fa...

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Divorced Dad Dating: When And How Do I Tell My Kids?


October 20th, 2015 . Jackie Pilossoph

I’m a divorced dad dating, wondering at what point do I tell my 3 boys? They are 11, 15 and 18.   Telling your kids you are dating isn’t an easy thing to do for any divorced dad or divorced mom. It’s very stressful, due to the uncertaint...

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Divorced Dad Parenting Advice: Ways To Stay Connected To Your Kids


September 4th, 2015 . Jackie Pilossoph

This is a guest post by Terry Gaspard, LICSW, offering divorced dad parenting advice that I think is truly valuable.   7 Ways Divorced Dads Can Stay Connected To Their Kids by Terry Gaspard   Recently, I received this heartfelt mess...

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Dating Advice: "Who is Going to Want me?"


August 1st, 2015 . Jackie Pilossoph

I have written so many articles giving dating advice about older, divorced women who ask the question, “Who is going to want me?” They feel that because they are middle-aged, have baggage, have children, and are possibly financially strapped that...

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Single Dad Dating: "Are My Kids Hurting My Love Life?"


July 7th, 2015 . Jackie Pilossoph

Jackie, I'm a single dad dating, and I want to know: Why do women look at dating a guy with kids as having an albatross hung around his neck? Are they that superficial?   This is the kind of question that has me thinking, ‘Huh?’ The reason...

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