The Subtle Art Of Not Judging Son's Girlfriends

And what it took years to learn.

By

Heather S. Kish

 
Published July 02, 2026
A mother and son's girlfriend warmly greeting with a handshake alongside smiling son standing nearby against a colorful patterned background
AARP (Getty Images)

Growing up, my oldest brother seemed to always have a new girlfriend. Being seven years older than me, the girls he brought home were worldly and sophisticated. They were beautiful and wore stylish clothes, the latest Farrah Fawcett hairstyle, and said words I’d never heard before. Exquisite. Sublime. Dither.

They were all perfectly pleasant and while it could be a little annoying to watch them drape themselves all over my perfectly boring brother, there wasn’t anything really wrong with them. At least not to my untrained 11-year-old eye. But then there was my mother.

Over the years I realized it wasn’t any of those poor girl’s fault. They were all relatively charming and polite. Came from good families. (Used sophisticated words). Helped set the table and clean up after. I mean, what more could a mother want? Well, plenty more it turns out. Because truth be told, no matter how pleasant looking, sounding, acting, these girls were, none could measure up to the standards my mother set for my brother.

My brother’s first serious girlfriend was two years older — 20 to his 18. Her name was Camilla and Doug brought her home to meet the family in early spring. They drove up to the house in my brother’s pride and joy, his yellow Datsun 270, which he had shined so bright and clean you could have eaten off the hood. Camilla stepped out wearing a suede jacket and a confidence that signaled she had already probably lived several lives. My mother took one look at her and whispered to my father, “She’s too old.” Then, as if remembering she was supposed to be polite, added, “And too …suede.”

That was the beginning of a long pattern. A girl was always too something. Too tall. Too short. Too quiet. Too loud. Too ambitious. Not ambitious enough. One girl was dismissed because she held her fork funny and another because she laughed at my father’s jokes. (“No one finds him funny,” she said, narrowing her eyes.)

I’d roll my eyes at her and swore I would never be like that. I’d be the cool mom, the welcoming mom, the mom who didn’t judge her children’s partners like they were contestants in a pageant only she knew the rules to.

And then — well. Life has a sense of humor.

Which brings us to present day and my son. At the age of 32, he has had more than his share of girlfriends over the years. I welcome them into our home as I do any of my children’s friends. The last three serious relationships he had each lasted over three years. And with each one I found myself feeling a little more and more like my mother each time.

They were all pleasant. They were funny and good-natured. They helped with the dishes and made Jack happy. But with each one I found myself wondering , is she really good enough for my boy? Is she smart enough to keep him challenged? Is she strong enough to keep him in line when he needs to be? Does she have strong values and morals and is she honest and kind?

And then more ridiculous questions started creeping in, the ones I never say out loud: How does she work with those long, fake nails? Does she vote? Why does she watch so much reality TV in bed? Is she ever going to get a real job? Does she know the difference between a sauté pan and a frying pan? Does she reuse sponges until they fall apart? Will she, for the love of God, ever get off her phone?

And then I’d hear it. My mother’s voice in my head, clear as day. She’s too old. She’s too suede. And suddenly I was the one squinting across the dinner table, analyzing a perfectly innocent young woman’s posture as if it held the secrets of the universe.

The worst part? I knew I was doing it. I could feel myself turning into her — my mother, the woman who once rejected my brother’s girlfriend because her hair was too straight. (Much of my childhood was spent being permed by her hairdresser for this very same reason.) I used to think that was absurd. And now I find myself noticing how someone chews their gum and think, hmmm.

But here’s the thing. The messy, funny, slightly painful truth of being a human: love makes us ridiculous. It makes us protective and hopeful and terrified all at once. It makes us repeat patterns we swore we’d break. It makes us want to bubble-wrap the people we care about, even when they’re fully grown adults who make their own doctor appointments and pay their own taxes.

Underneath all my nitpicking is something very simple: I want my son to be happy. That’s it. That’s the whole story. I want him to find someone who sees him the way I do — kind, funny, loyal, occasionally exasperating, but always worth the trouble. I want him to be loved well.

And maybe I worry that if I don’t scrutinize every detail, I’ll miss something important. Maybe I worry that if I let go, he’ll get hurt. Maybe I worry that if I stop trying to protect him, I’ll have to admit he doesn’t need protecting anymore.

But here’s what I am finally learning: he’ll find happiness on his own terms. With or without my approval. (But hopefully with!) My job isn’t to choose for him. My job is to trust that I raised a man who knows what love feels like — and what it doesn’t.

So I’m trying to be better. To be open. To be less critical. To be the mom who smiles instead of squints. The mom who listens instead of evaluates. The mom who remembers that every person who walks through the door is hoping to be welcomed.

And who knows — maybe the next girl will be the one. Or maybe she won’t. But either way, my son will be just fine.

And so, I suspect, will I.

Heather S. Kish lives in Old Town Alexandria, VA. A mom to two beautiful humans, she enjoys wearing lipstick every day, a cup of freshly sharpened pencils, green juice in the morning, and writing about the quirks and joys of life. She is a firm believer in romanticizing one’s life and expressing gratitude every day.