Clueless Silver Widower

By Amy Dickinson | October 20th, 2023

His lack of experience ‘wooing and flirting’ leave him stranded

A man on phone outside, for article on a clueless silver widower. Image by Andrei Zastrozhnov

A silver widower wants to meet women romantically but has no idea how. Advice columnist Amy Dickinson offers ideas.

Dear Amy:

I am an almost 70-year-old widower (politically liberal and atheist) who wants to meet new people. Especially female people.

Unfortunately, I have almost no experience.

I had a total of two dates in high school, both of which went nowhere.

I became very good friends with my best friend’s wife (friend-in-law?), and when they divorced, she and I got married.

So when it comes to wooing and flirting, I’ve got nothing.

It’s been four years since my wife died, and I have had zero possible romantic encounters.
My only teacher has been rom-com movies, which I am told do not portray real life. Sadly, I was planning my run through the airport already, but now I’m lost.

Where should I go to meet a possible romantic interest?

– No Game in Denver

Dear Denver:

Assuming that you are respectful, presentable, self-supporting – and that you can still drive at night – I’ll paraphrase a line from “Sleepless in Seattle” and say, basically, that the available women will throw a parade for you. You just have to locate the best parade route.

You may have spent the last four years in a fairly solitary state (understandable, given a global pandemic and the loss of your wife). If so, you might do best to view this as an effort to meet and make new friends (rather than to find women to date).

You should pursue activities that align with your interests, and then – start showing up. You live in a large urban area with a lively arts scene and surrounded by spectacular natural wonders. Start to explore! ( is one way to find groups to join.)

Your best friend’s wife found a reason to leave him and then marry and stay with you, and so I’d say that you’ve probably got a bit of Tom Hanks in there – somewhere.

Friends can help to “polish” you and even take you on practice runs where you can work on your greeting, meeting, and connecting skills. (In a rom-com, this would involve a montage of misfires, until you had proven your readiness.)

Friends can also introduce you to available women.

There are a number of online dating sites designated for “silver singles” like you. Peruse and research these sites to see if you are ready to meet women virtually.

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 – ranging from accepting a clueless silver widower to dark family secrets and DNA surprises. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. You can email Amy Dickinson at or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068.

©2023 by Amy Dickinson

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