A Challenging Granddaughter

By Amy Dickinson | July 15th, 2022

She’s already a handful, and her transitioning friend complicates things


angry granddaughter - photo by Dmytro Zinkevych Dreamstime. Her 12-year-old challenging granddaughter has added a transitioning friend to the complicated mix, and Grandma is exhausted. Image

Her 12-year-old challenging granddaughter has added a transitioning friend to the complicated mix, and Grandma is exhausted.


Dear Amy:

My 12-year-old granddaughter, “Casey,” often stays with me during weekends. Casey has a friend from school who she has visited several times. She has had a sleepover at that friend’s house – with her mom’s permission.

I met the friend’s mother briefly; I’ve only seen the friend from a distance.

My granddaughter led me to understand that her friend is a girl.

It seems now that although this friend was born female, she wants to transition to male, but is also gay, in that the friend wants to be a boy who is attracted to other boys. I am not comfortable with her having a sleepover with a boy.

Beyond that, I believe that 12 is too young to make decisions about sexuality.

My granddaughter is a handful – and that’s putting it mildly.

She lies routinely and is completely untrustworthy, so any information coming from her has to be taken with a grain of salt.

I don’t want to offend her friend or the friend’s parents, or have them think we would stop my granddaughter from going there simply because their child has a complicated sexual identity.

Today, for instance, I said that she could visit Casey at Casey’s house. She started blowing up my phone – and her mother’s phone – demanding to spend the night.

I’m at a loss about how to handle this.

Exhausted Grandma

Dear Exhausted:

Let’s set aside your granddaughter “Casey’s” friend’s gender exploration for now. If this information is coming from or being filtered through Casey, then I’d say you have a 12-year-old’s explanation of another 12-year-old’s gender journey.

The issue you should focus on is the question of where Casey will be spending the night when she is with you, and who will be in charge of her while she is with you: You, her mother, or Casey herself.

When Casey is with you, at least at the outset, the wisest course would be for you to welcome her friend to spend time at your house, or for you to take them on an outing together.

This would enable you to make an acquaintance with the friend, get to know their parents, and – speaking with Casey’s mom – to make an adult decision about a sleepover.

Casey’s privileges should also be tied to her own behavior: That’s basic parenting, and even though adolescent girls can tax their folks’ patience, you should do your best to stay open, patient, wise, loving, and nonjudgmental.

And always … trust but verify.


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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 challenging granddaughter 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

© 2021 by Amy Dickinson

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