The Sex Appeal of The Single Dad

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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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Relationships After Divorce Don’t Have To Be So Black and White

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June 1st, 2016 . Jackie Pilossoph

      Relationships after divorce are wonderful! Whether it’s a new friendship, a fun summer fling, or a deep love, I think relationships after divorce are richer, more fulfilling and more appreciated than they are in our yo...

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

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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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Dating Advice For Men: Why Women Primp So Much

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March 28th, 2016 . Jackie Pilossoph

          Dating advice for men, specifically in response to the comment below from a guy who doesn’t understand why women primp so much for dates.   I wouldn’t want to be around someone who...

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

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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

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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?

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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

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

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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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Online Dating: Is it Possible To Fall In Love?

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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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