Ask Amy: I’m fantasizing about my contractor

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

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.

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.

Dear Amy: “Trying to be Accommodating” described their discomfort hiking with friends who “dragged” their very young children (ages 2 and 4) on an eight-hour hike in the heat and over rough terrain. The kids did most of the walking themselves, and “cried the whole time.”

I was one of those kids.

I was taken backpacking at three years old. I learned to ski when I was two. When I inevitably fell behind, my parents said they wanted me to learn independence and stamina and that they would “just go on ahead.”

By the time I was 14 I’d been left on the Knife Edge of Mt. Katahdin in Maine, rescued by the snow patrol in Italy, and found by strangers who CARRIED ME ON THEIR SHOULDERS up Mount Washington – to name just three episodes.

This behavior is traumatic for those children and if they are pushed beyond their limits in this way consistently it will only get worse.


It’s one thing to “not spoil” or to “not give in” to a child.

It’s another thing to ignore actual distress.

– JA

Dear JA: Some readers responded that the parental behavior described in the question from “Trying to be Accommodating” amounts to abuse, and I agree.

In my response, I suggested ways for “Trying” to respond to the parents, urging them to lessen the length and challenge of this year’s annual hike, but I didn’t focus on the troubling parenting choices, and I should have.

Thank you for your response. Mount Katahdin is described as a “very strenuous” 8- to 12-hour hike. I could hardly bear to even watch a video of a hiker on the mountain’s famed Knife Edge (described as “deadly”); I cannot imagine being left there alone.


Thank goodness for the kindness of strangers, as well as the professional rescue squads who risk their own safety to help those stranded or left behind.

You sound like a true survivor.

Dear Amy: “Annoyed Little Sister” was bothered by her brother’s incessant bragging. Through childhood, their mother had always set them up in a competition, with the brother on the bottom.

This sounds like my childhood. Blatant parental favoritism damages sibling relationships throughout life. I’ve found ways to rise above it, but the sadness endures.

– Also Annoyed

Dear Annoyed: Parents write the script, while siblings spend the rest of their lives reciting it.


©2022 Amy Dickinson.