What my preschooler taught me about gender exploration

When Jackson and I drive home from pre-K four days a week, our conversations are usually quite run-of-the-mill. I ask him for details about his day and he rattles off what toys he and his friends played with, who fought with whom, and what the weather was like during playground time. He also starts singing nonsense songs, making potty jokes, and talking about what snacks he’s going to steal before dinner.

But recently, almost immediately as I was pulling out of the school’s parking lot, he yelled, “I want a dress!” Now, I’m the type of parent who, as soon as my kid says he wants to do something, I go to worst-case scenario: he says he wants to climb a tree and I envision his fall. He asks to help make spaghetti for dinner and I’m already treating burns on his hands in my mind. 

So, as soon as I heard the word “dress,” I pictured my sweet kid surrounded by 4-year-old bullies. Just as soon as I thought it, though, I mentally slapped myself out of it: I’m an LGBTQ parent who takes every chance I get to teach Jackson about thinking outside the box. Besides, the world and its bullies have changed tremendously since I was a kid. 

All of this ran through my brain in the approximate half-second during which I paused before saying, “Sure, sweetie.” And on to potty humor we went. 

Throughout that day, however, Jackson kept reiterating that he wanted a dress, and I noticed an almost sneaky smile each time he said it — like he was waiting for a reaction from me. 

So, I just kept affirming that I would be happy to get him one without prompting for more information. I knew this had to be coming from somewhere but didn’t want to make him think this whole dress thing was an issue by pressing it. He’d tell me when he’s ready, I thought. 

And sure enough, when getting ready for bed that night and talking about what prizes he may get if he accomplishes his “1,000 books before kindergarten” goal (almost at 400!), he again brought up a dress, asking which stores might have them. After I came up with Target (the best I could muster because Ashlee and I clearly are not dress people), he said, “My friends at school don’t think boys can wear dresses.” 

Ah, there we go! From there, I felt like I had an opening to ask him more: how this conversation came up, who felt what, who said what, how it made him feel. I made a mental note to text the mom of his one friend whom he said had his back in the Great Dress Debate of Room 6, but had to suppress the urge to rail about toxic masculinity and gender equity when he explained that another kid said it’s “weird” if boys like pink. I made myself avoid calling that kid a bozo and instead invested that energy into making those topics relatable for a 4-year-old: Mommy doesn’t like pink and you don’t like blue…I wear pants, why can’t you wear a dress?…Your sister wears hand-me-downs from you and your brother, and that’s okay. 


We ended up having a really good conversation about individuality, standing out, and being okay with not having the same views as everyone else. I was immensely impressed that even at 4 years old he knew that there just was something off about the strict gender binaries he’s surrounded by so often. And while I’m so proud that it sounds like he (and his friend) were okay sharing an opinion that put them in the minority, it left me feeling a bit sad that we’re already to the age where groupthink, judgments and pressure to fit in are starting to crop up. I mentally fast-forwarded to kindergarten, fifth grade, freshman year — and how much more complex conversations like this are going to keep getting. There goes that future forecasting by this worried parent again!

But it was also a good learning experience for me as a parent. While I feel like I know my kid inside and outside, sometimes better than I know myself, we’ve never really had to traverse a situation in which Jackson felt othered or intimidated by being in the minority. He’s a little white boy from the suburbs and — while having two moms certainly will eventually be a differentiator — I’m cognizant that he comes to life with a ton of privilege. I’m grateful that he’s gone 4.5 years rarely being made to feel uncomfortable by societal expectations. 

Having just a small taste of that showed me how he may deal with similar issues in the future. He wanted to talk to me about it but first had to test the waters to see if my perspective was in line with his — did I too think it was no big deal to buck gender norms, or would I laugh at his view? He had to feel accepted before he would open up to me. 

And I’m glad that I was able to (I think) say the things he needed. Granted, I screw up as a parent all of the time — like, every day, probably multiple times a day! (Tonight’s dinner included a 60-minute meatball fiasco: Jackson wanted sauce on them, then he didn’t want sauce, then he wanted cheese, then he didn’t want cheese, then he needed them cut and then he wished they were whole again; it drove me to become an apoplectic, shouting mess.) But I know him so well that, when he brought up this dress topic we had never talked about, I could tell there was something there to pay attention to, so I tried to. 

I hope I taught Jackson that he can trust me — that he can share something that may worry him and be met with openness. Because this situation reinforced to me that that’s my job. Now, I am confident that I won’t always agree with everything he thinks or does in the future, but this was my first opportunity as a parent to see that my perspective doesn’t need to always guide the narrative. Because I suppressed my inclination to worry and met him instead with acceptance, he opened up to me. And hopefully, we built an important stepping stone that will make all the tough conversations to come just a little bit easier.

Newsletter Sign-up