We moms all make mistakes, feel guilty, or wish we’d done a thing or two differently. And those parenting blunders can stick with us. What I usually recall are the times I thought I’d failed my kid when he was a toddler. Thank goodness I’ve finally gotten over my two Halloween costume-denial disasters!  Here’s how I messed up the first Halloween my boy wanted to be a girl.

“I’ll be Wendy.”

The Monday before Halloween in 1992, my two-and-a half-year-old son Harry was curled up in a leather chair watching Disney’s Peter Pan. I paused the VCR and waved the orange flyer a neighbor just delivered listing events that would turn our Milwaukee city street into a holiday theme park.

“Harry, guess what! The Halloween Block Party is Friday night! There’s trick-or-treating, a haunted house, scary stories, a piñata, and fireworks! And you get to dress up in a costume. You can be anyone you want!”

“Okay, I’ll be Wendy.”

“Wendy?”

He glanced at the picture frozen on the TV.

“You mean Wendy from Peter Pan?”

Harry nodded.

I managed a default smile. “Okay! Wendy it is!”

He turned back to Neverland, and I walked to the kitchen on automatic pilot.

What the hell just happened in there? Why did I have to bring up Halloween costumes while Harry was watching Peter Pan? What if he were watching Donald Duck? Would he have answered Daisy Duck? Possibly. Just two months earlier he’d told me, “Inside my head I’m a girl.” But what kind of Halloween costume was a blue nightgown, matching hair ribbon and brown wig?

I didn’t want anybody making fun of Harry dressed up as a girl.

Before bed, I told Ken about our son’s costume idea. His face fell.

“I really don’t want Harry to be Wendy for Halloween,” he said.

“I don’t either. But I already told him he could.”

“What?”

“Well, he caught me off guard,” I replied. “I just finished telling him he could be anyone he wanted.”

Ken didn’t tell me his reasons, but I figured they were similar to mine. I didn’t want anybody making fun of Harry dressed up as a girl. There were no bullies on our block. But there were two macho neighbor dads. I imagined them snickering as little Wendy climbed down our steps with a plastic pumpkin pail in one tiny fist, her skirt in the other.

This was the early ’90s. If a boy wore a girl’s Halloween costume, it meant he was going to be gay.

What will the neighbors think?

I wanted to protect myself, too. This was the early ’90s. If a boy wore a girl’s Halloween costume, it meant he was going to be gay. And according to some experts, a boy was gay because his mother was overbearing. I didn’t believe it. And I didn’t want to care what our neighbors thought. But I did care. Overbearing mother meant bad mother. I didn’t want anybody labeling Harry or me. Three days remained for me  to figure it out. And I didn’t want to screw it up.

The night before the block party, I drove across town through a foggy drizzle on a solo mission I dubbed “Operation Disney Store.” I felt like a double agent. I was about to trick my own kid.

Back home, I explained to Harry that the Disney Store didn’t have a Wendy costume, but there was a Peter Pan costume. I quickly flashed the showstopper cap.

“Look at this big orange feather!”

He reached for it.

“And check out this knife! Doesn’t it look real? But it’s only rubber! See?”

I stuck the blade into my palm. Harry gasped as the tip flexed harmlessly. He wanted that knife.

“Do you want to try on the whole costume?” I hoped aloud.

“Okay,” he said, stabbing his new knife into an end table.

The next day, Harry did not part with his fake weapon. I sighed with accomplishment and relief. But later I felt like a complete idiot, and not because I was wearing a Minnie Mouse costume.

Trapped in my own double standard.

The three of us walked outside at seven o’clock to meet up with Harry’s two best buddies and their parents. Louis was dressed as Count Dracula; Erica wore a Batman costume.

“It’s what she wanted,” her mom whispered.

The adults chuckled at how cute Erica looked as the Caped Crusader. An ache traveled up my arms. I felt shrunken in size, trapped in my own double standard. It was okay for a little girl to be a male superhero. I may have escaped raised eyebrows and silent ridicule, but I felt like a wicked Disney queen who lured Harry not with a poison apple, but with an orange feather and rubber knife.

Five Octobers passed before my neighbor Debbie asked if I had any costume ideas for her three-year-old son Georgie.

“I’ve got a really cute Peter Pan costume you can have.”

“Ummm, no thanks,” she said. “Alex wouldn’t want Georgie in anything too… uh… too feminine. You know, like tights.”

“Oh.” My eyes narrowed. I hadn’t thought about Peter Pan as feminine that night at the Disney Store.

My confession.

Two years ago, when Harry was 21, I confessed the whole story. He laughed.

“Do you remember me talking you into Peter Pan?”

“I’ve seen pictures of me as Peter Pan, but I don’t recall any of it as it happened. I do remember wearing Dad’s T-shirt as a nightshirt, though, pretending to be Wendy.”

“Really?”

“Yeah, if a shirt’s long enough, then it’s a dress.”

He paused.

“And, Mom, you have to admit that Peter Pan is probably the gayest kids’ costume ever.”

“It is?”

“Think about it,” he said. “On Broadway, Peter Pan is always played by a woman.”

“So, no emotional damage?” I half-joked.

“If there was, you made up for it,” he said, smiling.

I thought about how I handled things back then, the first Halloween my boy wanted to be a girl. I was just plain wrong. What difference did it make if a two-year-old wore what he liked? Screw the experts and everyone else.

“Listen, Harry, if you were two today and wanted to be Wendy for Halloween, then that’s who you’d be. You should get to be whomever you want, whatever your age.”

He kissed my cheek. “Thanks, Mom. I know.”

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