Advice from Amy: Older Man Baffled by Dating

By Amy Dickinson | November 12th, 2021

‘It’s clear to me now that I’ll never know women’


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Advice columnist Amy Dickinson advises an older man baffled by dating – especially after the latest fling that fizzled mysteriously.


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!”

What the heck does that even mean?

Not long after that she showed her character by ghosting me, so I’m comforted by the fact that I didn’t lose much.

– Confused by Women

Dear Confused: You seem to excel at the mechanics and dynamic of wooing: (Third–date dinner and a play? Well done!)

I can’t speak for all women (or even some women), and yet – the dynamic you describe as baffling seems – to me – to be simple human nature. When you retreat a bit, creating space, another person will instinctively move forward.

All the same, developing a sexual/romantic relationship can seem like participating in a tennis match choreographed by Twyla Tharp. You volley, she returns. You advance, she meets you at the net. You step back, she does a grand jete.

You have done nothing wrong. You noticed a pattern and communicated about it. She then told you exactly what you needed to know: when you held back, it created a desire in her.

Her return text might have brought on a round of fun flirtation. Instead, you seem flummoxed.

There are times when two people simply crash together. This is rare and wonderful.

For all of those other times, I suggest that you initiate less kissing and instead do more … leaning. Physical closeness, eye contact, a touch on the arm will telegraph your interest. If she’s into you, she’ll show it. You should let her.


Want to get even more life tips from Amy? Read more of her advice columns here!


In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart – from silver dating to DNA surprises. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. Ask Amy, P.O. Box 194, Freeville, NY 13068

© 2021 by Amy Dickinson

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