Ask Amy: Widower Relearns Heartache

By Amy Dickinson | August 20th, 2021

The lessons of love can be cruel


Widower has his heart broken Image

Dear Amy: My wife passed away in a car accident about seven years ago.

We were together for almost 25 years.

I had a few dates with women in the years since my wife’s death, but I didn’t meet anyone who really interested me. My last date was three years ago. I guess I just didn’t think I was ready.

I’ve been pretty content with my status until recently.

I joined a dating site and started talking to a woman. We talked for a week or so and got along great. We have a lot in common.

Every time I heard from her my heart would race and I felt what I haven’t felt in a long time. I was smiling all the time and in such a good mood.

Finally, we decided to meet. We met and afterward she told me she is only interested in friendship. I’m assuming that she just wasn’t attracted to me.

I get it, but it kinda knocked the wind out of my sails. I feel heartbroken. I don’t even want to look anymore and think I should just stay single.

My friends tell me to keep looking, but I don’t want to get my hopes up again and then be let down.

Any advice?

– No Confidence


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Dear No Confidence: I hope you would describe your emotions as more “heart-aching” than “heartbreaking.”

It is challenging to bounce back when you’ve been grazed by Cupid’s arrow. But matching and meeting is a bit of a numbers game, and the way back is to simply have more dating experiences – and to try to learn from all of them.

When I tried online dating (years ago) the most helpful advice I received – after my own near-misses – was to manage expectations until you meet your match in person, and to try to schedule an in-person meetup as soon as possible.

This means that once you and a prospective date establish your commonalities online, you refrain from overly emotional intimacies until you actually meet.

Your own previous dating experience showed you that when you met someone in person, sometimes you just didn’t feel a connection. It was not the other person’s fault, and it is not an indictment of their character, personality, or looks.

This feeling of connection is the mysterious work of pheromones, compatibility, the good timing.

The best way to protect yourself in the future is to not let your hopes soar until you experience a mutual in-person wow-wow-wow with someone. I hope it will happen for you.


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. 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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