My 3.5-year-old son wants to wear “girl” clothes. Why? Because they make him happy, and he doesn’t give a hoot what outsiders say. As a parent, what do you say to that?

Part of me wants to convince him to dress in accordance with social constructs, purely to protect him. Because, let’s be honest, some people are real assholes and no one wants their kid to be targeted by bubble-busters. Then, there’s the proud liberal mama part of me that wants to cheer him on, wave a big foam middle finger at naysayers, rally vehemently for his happiness, and celebrate his bravery to unabashedly seek his own contentment in a way that in no way harms others. Seriously, now, my preschooler has more self-direction and more internal fortitude than I do at 33!

Here’s the background story on our light-shedding conversation. We were driving back from a morning at my parents’ house and I asked my 3.5-year-old what he wanted to be when he grew up. “A teacher,” he replied. I asked if he’d teach little kids or big kids. He said he’d teach big kids and, “wear a long, long wig and a beautiful dress.” I asked him why he’d wear a wig and dress to teach, to which he simply answered: “Because girl clothes make me happy.”

Seeing as he was, at that moment, wearing the outfit I’d laid out for him — overalls, a long-sleeve shirt, rain boots, and a rain coat — I asked how he felt in his present ensemble. He looked down at his denim overalls, “Not happy,” he said, “I’m not beautiful in boy clothes. Girl clothes are pretty.” Fair point. Dresses, tutus, and gowns are pretty spectacular. Traditionally male attire just doesn’t carry the same pizzazz.

“How about your pink and blue button-up shirts,” I asked, “do you feel handsome in those?” He thought for a moment. “I’m not pretty in those shirts. I want to look pretty.” I asked how being pretty made him feel. “Happy!” He grinned.

My internal dueling parts battled within me as I drove down the highway. If I discourage this desire now maybe I’ll be able to protect him. Or maybe I’ll simply make him feel as if it’s wrong… as if he’s wrong. I can’t risk that. But people are assholes, I lamented. People are also wonderful, supportive, and open-minded, I countered. I took a deep breath.

“You know,” I said, “Mommy loves you no matter what you wear. However, some people only like others to dress a certain way. Those people can sometimes be mean if they see someone dressed in a way that’s different from what they think is right because the difference scares them. What would you do if someone like that was unfriendly to you.” He thought silently. “I’d say, ‘I’m sorry!'” “You apologize? Why?” I asked him in shock. “I’d say, ‘I’m sorry I scare you.’ Then I’d ask them if I can wear the dress because it makes me happy and they’d say, ‘ok. You can wear that.’ And I would. And I’d be so, so happy.” I praised the thoughtfulness of his answer.

“Your boy friends,” I continued, “wear clothes boys usually wear and your girl friends wear clothes girls usually wear. What if one of your friends asks why you’re wearing a dress?” “I’d tell my friend the dress makes me happy.” “What if someone makes fun of you?” I asked. “They should say, ‘I’m sorry.'” He replied. I asked if being teased about wearing a dress would hurt his feelings. He thought. “I’d be happy I’m wearing a dress. I’d be pretty.”

I told him that in first grade, if he attends his sister’s school, that he’d need to wear the boy uniform. I asked if he’d be ok with that. He said he would because he would wear girl clothes at home. “I can wear girl pajamas!” He exclaimed. “Please you get me girl pajamas? Today?!” I laughed with amusement at his problem-solving and excitement. “Let’s look for your sister’s old nightgowns. She has ones she’s outgrown.” “Ok !” He said as he kicked happily in his car seat, grinning wide. “We have to ask Daddy first though. If he’s ok with it, then it’s fine.”

The moment The Hubs walked through the door, our 3.5-year-old hurled the question: “Daddy, please may I wear girl pajamas?” And so tonight our middle son will be donning an Ariel nightgown to bed.

Because it makes him happy.