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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How To Talk To Women: 12 Tips


June 25th, 2015 . Jackie Pilossoph

Jackie, I’m recently single and I’ve been in a relationship for so long that I forgot how to talk to women. Also, will I have patience for the games?   Recently single is a tough place to be. It’s scary, your self-esteem probably isn’t...

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Dating Advice for: "How Do I Not F* This Up?"


June 2nd, 2015 . Jackie Pilossoph

Jackie, I need some dating advice. Say you go out on two first dates on two consecutive nights and they’re both awesome. How do I not F* this up?   Do you realize how many men and women would KILL to be in your shoes? Over and over aga...

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Dating Advice: "I Want To See Her More Often"


April 27th, 2015 . Jackie Pilossoph

Jackie, I need some dating advice. I’ve been on a handful of dates with a woman, who my gut says is a truly sweet, genuine woman. We’ve had great dates, talking, laughing etc. for hours on end.  I’ve expressed to her that I want to see her...

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Single Dad Dating Doesn’t Want to "Waste Time"


March 27th, 2015 . Jackie Pilossoph

A single dad dating asked me this question:   Is it wrong to not want to go out on dates unless you feel there is potential for a long term relationship? As a divorced dad who has full custody of my 13 year-old daughter, I don’t have time to...

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Dating After Divorce: Are Divorced Guys A Turnoff To Women?


March 20th, 2015 . Jackie Pilossoph

I received this email from a divorced man who is about to start dating after divorce. How do women feel when they hear that a man is divorced? I feel that when I start to date, they’ll turn away, thinking that there is something wrong with me si...

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Divorced Chick Gives Dating Advice to 20 Something Guy


March 6th, 2015 . Jackie Pilossoph

If you’re a young, single guy in your twenties, who better to get dating advice from than a middle aged divorced woman? (me.) Think about why it makes sense. I can talk about the mistakes I made, I can tell you what I liked and didn’t like, both ...

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Dating After Divorce: Is it a Matter of Getting Around To It?


January 16th, 2015 . Jackie Pilossoph

When it comes to dating after divorce, everyone has his or her own timetable. There are so many reasons that can cause apprehension: the lingering hurt from the divorce, kids, bitterness, fear of feeling awkward, shyness, insecurity, or the worst one...

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Should This Newly Divorced Man Move In With His Girlfriend?


December 15th, 2014 . Jackie Pilossoph

I received this email from a newly divorced man: It has been not quite a month since the date of divorce. I've been seeing someone I met while I was separated. We really hit it off. I mean more so than I expected. Honestly I wasn't looking to fall...

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Dating Advice For Men: Don’t Be This Guy


December 6th, 2014 . Jackie Pilossoph

I want to offer some dating advice for men that involves an example of the guy you should really try not to be. I recently fixed up a girlfriend of mine with a guy I know (and like a lot.) They went out and really hit it off, staying out for hours...

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