By Maureen Kelleher

My child has always struggled with pronouns. Back when Bobby was about two, when we first started going to Music Together, we learned a song called “Me, You and We.” It was very simple. Point to yourself and sing, “Me. Me. Me-me-me, me-me-me, me, me.” And so on. Then point to your mom, dad, grandparent or caregiver and sing, “You. You. …” And so on. Then enjoy the bliss of “We”—hold that long e note while holding hands or giving your loved one a hug. Then sing, “We are you and me.”

This helped, but after class, Bobby would still mix up who was me and who was you.

Bobby also had trouble with third person. “I’m she,” he would proudly announce.

“Uh, no, you’re he,” I would offer, trying to correct as gently as possible.

As Bobby grew older, he became more insistent. “No, Mom, I’m a girl.”

Digging deep into old, unhealthy habits, I would avoid the issue. Besides, I had a theory. Bobby’s first word was “agua.” His Papa is from Mexico City. Spanish doesn’t use pronouns as much as English—the inflected verb does all the work.

Quiero—I want

Quiere—He or she wants

No pronoun required.

It’s all linguistic, I told myself. Although my chatty, English-dominant child quickly mastered a huge vocabulary and spoke in full sentences early on, we still have these funny little moments when I know he’s learning two languages. I figured pronouns was just one of those moments.

But linguistics didn’t solve the problem of the nail polish. Personally, I hate nail polish. Can’t stand the smell. I got my nails done for my wedding and that was it for me and toluene.

Our babysitter, Nancy, a twenty-something Mexicana—thought differently about nails. It seemed like every couple of days there was a new color scheme on her hands. When they did art projects, Bobby started painting his nails with watercolor. Once day Nancy did his nails without asking permission first. I came home and Bobby eagerly waved his sparkly blue fingers at me.

I was less than impressed but chalked it up to life with a preschooler. My husband was less impressed—even worried—but in his usual fashion kept it mostly to himself. Eventually, I bought a bottle of quick-dry green nail polish and spilled some on my shorts while giving Bobby a manicure.

That Halloween was a close call. Bobby—who loved trains—wanted to be a Chicago subway line. But would he be the Pink Line or the Green Line? Both were his favorite colors. Fortunately, at Target we found matching green pants and a plain green shirt first. That satisfied him. My husband painted the Green Line map—all 28 stations—on the front of Bobby’s shirt.

*   *   *

Some boys—pink boys, girly boys, boys who like girl stuff—are unmistakable. They love Barbie. Pink everything. Sparkles everywhere.

Bobby wasn’t like that. He liked trains, dinosaurs and roughhousing with his Papa. He didn’t like any animated characters—not Barbie, not Batman.

But around age 3, he stopped wearing underwear. I worried about this until his preschool teacher told me her son went commando for a while. When she told me Mateo—who was the older, stronger, Peter Pan to Bobby and the preschool Lost Boys—didn’t wear underpants for a while, I just let it go.

Then Bobby wanted to grow his hair out. I refused. I like to think I wouldn’t have let a 4-year-old girl grow her hair past her collar either, on account of the tangles. But I did keep cutting back the hair over Bobby’s ears, and he didn’t like it.

“When I’m 18 I will grow my hair down to my feet,” he insisted.

“When you can brush it yourself every day, and put it in a ponytail on your own, you can do what you want,” I grumbled.

*   *   *

“Mom, I’m Roberta,” Bobby informed me, a few months into kindergarten. This happened right around the time we went to Target in search of school supplies and Bobby spotted a purple-rainbow-sparkly high-top atop a shoe box. In the girls’ aisle.

“Mom, can I get those?” he asked, awed by their splendor.

My stomach tightened. I didn’t want to set him up as a walking target for bullies. Sending him to school—even our lovely, diverse, maybe overly-nurturing public magnet school—with those shoes on felt like giving him a t-shirt that read: “Sissy.”

But then I thought a little harder. Why should I be a bully? They’re just shoes.

“OK,” I said. “Let’s get them. Some kids might tease you about them or say they are for girls. How do you feel about that?”

“I don’t mind,” said Bobby, emphatically.

We bought them and he wore them out of the store. As we left a sales clerk spotted them and said, “Nice shoes!”

The next day I worked late and a friend picked him up after school. When I arrived at her house, the friend described the buzz she had overheard about Bobby’s new shoes. A boy took one look and said, “Those shoes are for girls.”

Bobby’s teacher heard the comment and stepped up right away. “Girls and boys can wear them,” she said. A discussion ensued, involving Northwestern purple—the exact shade of the laces—and apparently when the teacher said, “Football players wear purple,” light bulbs went on over a few of the other boys’ heads. End of subject.

“Thank you for supporting my son’s right to self-expression,” I emailed her.

Not long after, I emailed again. “You will see the name Roberta on today’s homework. This is not a mistake. At home Roberto likes to pretend he has a twin sister. I didn’t want you to think he was misspelling his name.”

Around Veterans Day, I took Bobby with me on a business trip to Michigan. At the hotel he asked, “Mom, make me a dress.”

I took the white woven blanket off the top closet shelf and wrapped it around him like an evening gown with a train. For 45 minutes he danced and pranced and swished his long skirts around our hotel room. I danced alongside him.

*   *   *

In mid-December we had a surprise. Our first-choice school—a nearby charter with a dual-language program—called us to say they had a space. The commute to our lovely magnet school—an hour or so each way—was killing me. Bobby loved his school and did not want to switch.

What could make this bearable? I thought.

When I met with the teacher and assistant, I told them about Bobby. By then I knew the official term: gender non-conforming. “He says he is a girl and his name is Roberta.”

The teacher—a thirtyish man with poufy hair, shiny red sneakers and a husband—nodded. “If he wants to be Roberta and go in the girls’ line, we can do that,” he said.

My heart leapt. We could do this, I thought. But my husband will freak. As it turned out, my husband grumbled, but he didn’t freak.

Bobbi started wearing a skirt in public over winter break. She had a playdate with some new friends as Roberta. We all had trouble with pronouns. I could say her name but sometime “he” would pop out before “she” arrived in my mouth. No one cared.

During the playdate, the youngest child, a first-grade boy who played stomp rockets with Roberta and wrestled her to the floor while she laughed gleefully, called her “he.” “She,” he corrected himself.

*   *   *

When we went as a family to meet the teachers the day before school started again, the teacher asked Bobbi, “Which washroom do you want to use?”

“The girls,” my child replied, without hesitation.

“Hi, Roberto,” an administrator greeted her.

“I’m Roberta,” she corrected immediately.

Puzzled look.

“She’s Roberta,” I said.

“Oh, OK. Hi, Roberta,” said the administrator.

On Bobbi’s fourth day at her new school, she wore her favorite blue skirt and purple leggings with tulle flowers at the ankles. Despite the remains of an early January blizzard, she refused to wear snowpants. When Bobbi came out the door after school, the hood of her jacket hid all her hair, like a nun’s wimple. All I could see was her face, her blue jacket, blue skirt and purple leggings.

It was the first time I saw my girl.

Then we went walking in the snow. Bobbi got snow all over herself. “You’ll have to change when we get home,” I told her. At home, I handed her a pair of gray Toughskins and, bam! she was a boy again.

I’ll be having trouble with pronouns for a while yet.

This piece first ran here at Brain,Child magazine.

Author’s Note: My child’s name has been changed to protect her privacy.

Maureen Kelleher is a Chicago-based education writer.