Dating A Divorced Woman With Kids: What You Need To Know


March 10th, 2016 . Jackie Pilossoph

My heart went out to a sweet guy who emailed me to ask for my advice about dating a divorced woman with kids. The reason I felt so badly for the guy is because he has never been in this situation before, and because of that, the relationship is causi...

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Advice For Guy Dating a Woman With a Young Son


February 14th, 2016 . Jackie Pilossoph

      I am dating a woman with a young son. She is amazing, but sometimes I feel suffocated. I’m not sure I should stay in this relationship. We are both very young—24 and 26 and I’m not ready to be a father. I don’t e...

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Older Guy Younger Woman: Can It Work?


February 10th, 2016 . Jackie Pilossoph

I’ve never understood the older guy younger woman relationship. Why would a man over 40 want to date a woman in her early twenties? Here are the possible reasons, in my opinion.   She’s hot. She's fun. She’s got a lot of energy ...

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3 Things I Would Tell Someone Getting Married


January 16th, 2016 . Jackie Pilossoph

      A question I received from a male reader: What are three things you would tell someone getting married?   Someone just asked me the other day, “How can you give relationship advice to married couples when you are divorc...

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Online Dating: Is it Possible To Fall In Love?


October 25th, 2015 . Jackie Pilossoph

What’s the best way to get over falling in love with someone you met via online dating that you’ve actually never met in person?   Here is the good news. Getting over this person will not be difficult for you at all. Why do I say this? Bec...

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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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20 Rules For Dating After Divorce: But Really…There Are No Rules


October 15th, 2015 . Jackie Pilossoph

When do you think is the appropriate time to start dating after divorce? I don’t have anyone in mind, just a general question. 13 months into the divorce process. I haven’t moved out yet due to financial reasons. Very ready to try dating. Thi...

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Not Your Typical Dating Advice, But Guaranteed to Make You Laugh!


September 14th, 2015 . Jackie Pilossoph

I happened to come across this article in TheBlot Magazine, and laughed so hard I almost cried. Written by author and college professor, Gary Buslik, the piece is not only funny as hell, but there is some valuable dating advice to be gained from it; ...

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Stop Looking for The One and Focus On "The Ones"


August 26th, 2015 . Jackie Pilossoph

I’m not sure there is a man or a woman on this planet who isn’t looking for the one, and who hasn’t asked the question, “Where the hell is he or she already??” Let’s not kid ourselves and say we don’t care. We do. It’s an innate human...

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Dating Advice For Guy Asking, "How Do You know If She’s Moved on From Her Divorce?"


August 22nd, 2015 . Jackie Pilossoph

Here is some dating advice for a guy asking, "How do you know if the woman I'm dating is ready to move on from her divorce?" Dating someone new can be scary in some ways, especially if you really start to develop feelings. Chances are, if you have...

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