11 Pieces of Advice for Men Over 50


April 25th, 2022 . Jackie Pilossoph

I received the message below from Mike, a 53 year old guy who has been both widowed and divorced, and who has some words of wisdom for men over 50. Thought I would share, and in italics below are my comments. Thanks so much, Mike!  Jackie, I w...

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Divorced Guy: “I Will NEVER Get Married Again. Ever”


March 20th, 2022 . Jackie Pilossoph

This is an email I received from a 50 something year-old divorced guy who got got divorced because his wife cheated on him. He was very surprised and hurt by the cheating and said he never suspected it. I believe he has been divorced for a couple of ...

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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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