Life Advice



Ask Amy: Dater fears he will never be a player

Amy Dickinson, Tribune Content Agency on

Dear Amy: I’m a man in my late-50s.

I’m currently dating – or trying to date.

It’s clear to me now that I’ll never know women, so please explain what just happened here: I met a woman on a dating app, and we had one of those perfect first dates – lots of laughs, lots of agreement, finishing each other’s sentences, easily planning the next date.

At the end I kissed her, and she kissed me back.

Second date, I made dinner. We had a great time and great conversation. We had agreed beforehand that this was not an overnight. Another good date, and at the end, we kissed.

Third date was dinner and a play. At dinner I walked around to her chair and kissed her, and she kissed me back.


But by now I was realizing that I was the only one reaching in for a kiss.

She didn’t pull back or shy away, but she never initiated it.

So, at the end of the date, I refrained from kissing her.

Later on, I texted her and pointed out the fact that I had deliberately not kissed her, and she responded, “I know, and that made me want to kiss you!”


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