Dear Gefilte: My Son Wants To Be a Girl & I'm Ashamed – Kveller
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dear gefilte

Dear Gefilte: My Son Wants To Be a Girl & I’m Ashamed

Dear Gefilte,

My 4-year-old son wants to wear dresses. And nail polish and princess outfits and now ballet slippers. He even says that he wants to be a girl because he “likes girls better.” I want him to be whoever he is. And it’s easy for me to say that I am going to let him choose his own path no matter what. But saying it and doing it are two very different things.

I’m not a big macho guy, but I feel a little ashamed when he wants to do this. I’m not disappointed in him at all. So the answer is not “just love him no matter what,” because I will—without a doubt. My struggle is loving myself and dealing with my own shame and judgment around this. What can I do?


Ashamed that I’m ashamed

READ: My Black Son’s Pink Shoes

Dear Ashamed,

Check this out—here’s a little game I like to call Name that Gender!

I tell you a few distinguishing traits and you tell me if I’m describing a “he” or a “she.”

On your mark, get set, go!

1. Loves ballet slippers, princess dresses, and nail polish
2. Listens to Eminem and Steely Dan while hammering nails
3. Toni Braxton and Sade, too
4. Vegetarian
5. Often succumbs to social anxiety
6. Unresolved daddy issues
7. Spent two years chasing after a German girl and trying to kiss her on her dad’s bearskin rug
8. Martial arts enthusiast
9. NPR subscriber
10. Seltzer connoisseur

Give up? Yeah, that was sort of a trick question. It was me.

Or was it you?

READ: My Problem with All Those Gender Reveal Parties

Ashamed, have you ever read this incredible book by Lori Duron called, “Raising My Rainbow: Adventures in Raising a Fabulous, Gender Creative Son”? Her blog is also spectacular and so honest. I love when she writes from the point of view of her son: “I don’t fit into a category or a box. I may not be easy to explain or understand, but if you approach me with an open heart and an open mind, I can guarantee that I will change your way of thinking.”

The point is, I think you love your son immensely and as you said, you will love him this way no matter what. And I think you’re doing a beautiful job already because you are asking questions and facing his nail polish head on. The question is, how can you love yourself this unconditionally, too?

dear gefilte

Shame is defined by Merriam-Webster as a feeling of guilt, regret, or sadness that you have because you know you have done something wrong.

And here’s the expert on shame, research professor Brene Brown, PhD: “Shame is the most powerful, master emotion. It’s the fear that we’re not good enough.”

She also says: “The truth is: Belonging starts with self-acceptance. Your level of belonging, in fact, can never be greater than your level of self-acceptance, because believing that you’re enough is what gives you the courage to be authentic, vulnerable and imperfect.”

So what do you think it says about you that you let your son wear what he likes and follow his imagination? What does it mean to support him as he explores and experiments? To give him love and validation, with or without the frills?

If you ask me, I think it says that you are deeply loving and generous. It says you are strong, authentic, and you honor your son’s truth. Which really is the greatest strength we as humans can have, right?

Here’s a Jewish perspective on shame that I think is quite brilliant, from Rabbi Jeffrey Sirkman of Larchmont Temple. Sirkman is talking about Jacob feeling deep shame over tricking his brother out of a birthright and then meeting his brother again many years later, with that shame weighing him down:

“(Jacob) meets his brother face to face, after having wrestled with his conscience and received a new name–God-Wrestler–and recognizes that his brother’s face is a reflection of holiness…Only when are able to stand face to face with the source of our shame and see beyond it, or see in it a potential for being better/being more, can we grow into our most sacred selves.”

Bonus round: If you were to die tomorrow, how would you like your son to remember you?

READ: Target Decides to Phase Out Gendered Advertising

That’s harder to think about than a walk down the street in a ball gown, right?

Ashamed, my prescription for you is every time you are feeling overwhelmed by shame or confusion, take a deep breath. Find a way to empathize not only with your son but also with yourself. For instance, try on one of your son’s tiaras and repeat the Serenity Prayer: God grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.

I mean this sincerely. Just to see what it feels like to let go of that judgment that is strangling you.

And remember:

A cheetah can always outrun you.

A gefilte can always out-bob you.

But you—and only you—can be the greatest dad your son will ever know.

With love and schmaltz,


Have a question for Gefilte? Send it to, and you might just get an answer. 

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