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Heavy Meddle: Our 6-Year-Old Son Cross-Dresses. Should We Be Worried?

She's conflicted about her child's choices. Her husband worries their son will be ridiculed.(Andrew Branch/Unsplash)
She's conflicted about her child's choices. Her husband worries their son will be ridiculed.(Andrew Branch/Unsplash)

Welcome Meddleheads, to the advice column where your crazy meets my crazy! Please send your questions. You can use this form, or send them via email. Not only will you immediately feel much better, you’ll also get some advice.

Hugs,
Steve

...

Dear Steve,

My little boy, who is 6, cross-dresses for fun. He comes home from school, strips to his underpants, and throws on a dress, a crown, sometimes a boa and tiny high-heeled shoes, and just chills. He has all of these things because my husband and I have done our level best not to freight his sartorial choices with gender-specific meaning and to buy what he asks for. From his earliest days, pink has been his favorite color. He has always preferred mermaids to Magna-Tiles. He flips through the kids’ clothing catalogues that arrive and dog-ears pages with dresses festooned with flowers and woodland creatures. He goes to a school where kids are welcome to wear what they like, identify how they choose, use whichever pronoun suits. He asked for a new spring dress, and I obliged.

Recently, while skiing with my son, my husband was upset that someone thought he was a girl -- his used skis have Hawaiian flowers on them ... 

So, I feel like, on balance, we are handling his preferences well. If he wants sparkly sneakers when it’s new shoe time, he gets them. But lately, my husband has started expressing his consternation. He doesn't want our son singled out, picked on, ridiculed. Recently, while skiing with our son, my husband was upset that someone thought he was a girl — his used skis have Hawaiian flowers on them, though the rest of his ski ensemble is very gender-neutral. I tell my husband that it's people’s limitations and problems, not ours, if they think a boy who loves flowers is a girl. But I now feel like I have to defend my son's choices — and mine to support him — to his father. It's hard, because I'm conflicted, too. (I recently discouraged our son without telling him the real reason from wearing his favorite hot pink, sequined shirt with black leggings on a visit with my parents because I know my parents.)

What advice might you have for a couple of parents who don't want to stigmatize their child's choices, who want to be accepting and open, but who nevertheless see their little boy drifting more toward being a little girl and feel quite unsure of what to do about that, other than let him go there?

Yours,

Open But a Little Freaked Out, Too
...

Dear Open But,

I feel you. For most of his first three years, our son’s favorite garment was a blue dress with yellow flowers. He also loved to play with makeup. He had an older sister, whom he adored, so his interest in girly stuff made sense to us. But there did come a moment when he wanted us to buy him a pink leopard-print lunch box for his first day in kindergarten. And my wife, who was with him at the time, simply couldn’t pull the trigger. She worried, as your husband does, that other kids (boys, specifically) would give him a hard time. I disagreed with my wife, but I certainly understood her perspective. In the end, she made an excuse to avoid getting him a new lunch box.

Yup, another heroic moment in parenting!

Your son’s interest in “girl’s clothing” is more consistent. But you’re far from alone. Do a little research, if you haven’t: It’s normal for young boys and girls to want to dress up in the clothing of the opposite gender. It’s a form of imaginative play that would happen a lot more if our culture wasn’t so crushingly insecure and hung up on gender stereotypes. The fact that your son attends a school that recognizes gender fluidity strikes me as evidence that this is a common situation, not a rarity.

Pretty much any expert on child psychology (or life) will tell you that the most important thing here, by a factor of ten, is that you are loving and supportive of your son, so that he learns to love himself. That’s his ultimate safeguard against a world that is imperfect and too often intolerant.

But I also think it’s important for both you and your husband to be honest about the reasons you find your son’s affinity for feminine clothing unsettling. It is solely anxiety about social disapproval and bullying? These are real concerns, particularly in a country that is, in certain precincts, regressing when it comes to gender hang-ups, becoming more rigid and less accepting. (The idea that your own parents would look askance at their grandson if he decided to wear something “too girly” kind of says it all.)

My son’s cross-dressing definitely roused issues within me about my own masculinity. And another part of me was just kind of bummed that my son had no interest whatsoever in playing catch with me.

At the same time, it’s important to parse how much of this is coming from the world around you, and how much from the world inside you. Your husband, for instance, might find it troubling (consciously or unconsciously) that your son doesn’t identify more strongly with his gender. My son’s cross-dressing definitely roused issues within me about my own masculinity. And another part of me was just kind of bummed that my son had no interest whatsoever in playing catch with me. What I had to figure out (and it took some doing) was that my son being sensitive and artistic didn’t make him less masculine, just as my daughter being athletic and ambitious didn’t make her less feminine. I’d just been allowing a corrupt version of those concepts to rule my thinking.

Having said all that, it’s also important for you to think about why his sartorial decisions lead you to conclude that he’s “drifting more towards being a little girl.” Does he behave in other ways that suggest he feels a disjunction between his body and his gender identity? Does he talk about wanting to be a girl? (If he did, I suspect you would have mentioned that in your letter.) Because again, think about it: He goes to a school that gives its students the freedom to identify themselves as they like. It stands to reason that, in a setting free of patriarchal judgment, kids would feel liberated to dress (and play and imagine) as they wish without it having to mean anything about their gender, or their orientation.

So here’s the deal. Two complicated things can be true at once. The first is that we live in a world full of idiotic stereotypes based, mostly, on male insecurity. Our popular culture, accordingly, is overrun by images of macho men and women as sexual hood ornaments. This warps our own thinking. The second is that people are complicated; they contain multitudes. All you can do as a parent is love your kid (and set reasonable limits for him). And the biggest part of that is letting him figure out who he is, one hot-pink, sequined garment at a time, and supporting him along the way. The fact that you’re thinking about all this so compassionately tells me that you and your husband are doing great. So is your kid.

Onward, together,
Steve

Author's note:I promised myself I wouldn’t pollute my answer with any reference to the recent decision by the Department of Justice to start to roll back the rights of transgendered people. But I’d be happy to hear from you all about the connections between the personal and political in this realm. Or any of your always good counsel, in the comments section below. Also: please send along a letter to Heavy Meddle, if you haven't. You can use this form, or send your questions via email. — S.A.

Heavy Meddle with Steve Almond is Cognoscenti's advice column. Read more here.

Headshot of Steve Almond

Steve Almond Cognoscenti contributor
Steve Almond’s new book, “Truth Is the Arrow, Mercy Is the Bow” will be out in 2024.

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