Dating Advice: Call Too Often I’m a Stalker, Don’t Call Enough I’m a Jerk


May 3rd, 2016 . Jackie Pilossoph

        Said to me by a single guy in his early fifties seeking dating advice:   “I have a great topic for you to write about. As a guy, one of my biggest issues in dating is that these women are impos...

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Divorced Men Often Get Unexpected Gifts: Attention And Feeling Desired


March 16th, 2016 . Jackie Pilossoph

        A male reader posted this comment on Divorced Guy Grinning. I find what he had to say very typical in what happens to divorced men:   Wait until you're divorced and you meet someone who makes you...

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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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Dating Advice: My Divorced Date Wore Her Wedding Rings Last Night


November 25th, 2015 . Jackie Pilossoph

  I need some dating advice. I’ve been dating a woman for the past few months and her divorce was final about two months ago. Last night we went out and she randomly had on her wedding rings. It’s very hard to give you dating advic...

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Dear Future Husband (In Second Marriage)


May 13th, 2015 . Jackie Pilossoph

In the lyrics of her hit but controversial song, “Dear Future Husband,” Meghan Trainor demands from him: dates, flowers on their anniversary, being treated like a lady, being told she’s beautiful, apologies after every fight, his time, and a ri...

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Dating a Woman in Her Forties? Or Are you More Likely To Go for a Younger Girl?


December 3rd, 2014 . Jackie Pilossoph

This is a guest post by my friend, "Doug," a 49 year-old who offers some great insight into dating a woman in her forties versus choosing a younger girlfriend. The choice is yours, and there is no right or wrong answer, but Doug offers a good perspec...

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