A Cougar Hears the Call: An Older Woman’s Dilemma

By Amy Dickinson | August 19th, 2022

To act on her feelings or not, that is the question Ask Amy answers


contractor doing electrical work. photo by Antoniodiaz Dreamstime. The “cougar” – an older woman – finds herself attracted to a much younger man – the contractor working on her house, no less. See what Ask Amy advises. Image

An older woman – the “cougar” – finds herself attracted to a much younger man. He is the contractor working on her house, no less. See what Amy Dickinson of Ask Amy advises.


Dear Amy:

I’m a senior woman, divorced for more than half my life.

Recently I’ve hired a worker (30 years younger than I) to update my home, which badly needed some work done.

During the time he’s been working in my home, we’ve become friendly.

I sincerely respect him and strongly believe he respects me, as well.

Lately I find myself having fantasies about us becoming “friends with benefits,” and he has made a couple of comments which lead me to believe that he may feel the same way.

I’m uncomfortable with these feelings, but seem powerless to stop.

I’ve never in my life done anything like this and truly don’t want to now.

How should I handle this extremely uncomfortable situation?

– The Older Woman … the “cougar”

Dear Older Woman:

Fifteen years ago, I called a guy I went to high school with to renovate my house. He renovated my life, instead.

My point is that it is possible to meet “Mr. Right” – or “Mr. Right Now” – in your own living room.

If you truly don’t want to become involved with this man, then you should limit your time spent with him, get him to finish up the contracted work, pay him, send him on his way and continue to live your life – as is.

However, life is short. Hot sex is great.


Grandma cuts ties because of “cougar” accusations


Understand that there are qualifications about being and staying safe. Do what you can to find out about this man beyond his Yelp reviews, and if you decide to go for it, use a condom.

No change in your circumstances is guaranteed to be seamless, happy, or easy.

Any involvement with him would bring on questions, uncertainty, and quite possibly an uncomfortable upheaval for you.

But – I repeat – a sexual reawakening is life affirming and lovely.

Even the emotional pain that might accompany the possible outcome of the “friends with benefits” scenario can be worth it, because reconnecting with your sensual side will remind you to love yourself, to live fully in your own body, and that it’s OK to be daring and occasionally wild.

The Emma Thompson film “Good Luck to You, Leo Grande” (currently streaming on Hulu) might inspire you.


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 a curious cougar 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

© 2022 by Amy Dickinson

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