It was Saturday afternoon, March 2nd, 2019, in a suburb in Silicon Valley. I stood in front of my closet, half-naked, confused.

I was meant to be getting dressed for a work party. Lacuna Technologies was still small, just twelve employees. I’d been the first engineer hired. This was my fourth corporate adventure with our CEO, and he trusted me to build both software and teams. For this, our first company event, he’d gotten us a private room in a medium-chi-chi Italian restaurant in Palo Alto.

I recalled mention of a dress code, so I looked at the invite again. It specified “cocktail attire.” I puzzled over the exact definition, staring at my two sport coats and three pairs of slacks. Normally, I would consult on matters of attire with my wife, Shannon, as this was her area of expertise. But she’d recently moved into an apartment in San Francisco because of her new job as lead wardrobe person for the SF production of Hamilton. At that moment, she was backstage at the Orpheum Theater, working the matinee.

Formal wear and I never got along. Sport coats felt like straitjackets. I willfully never learned to tie a tie. (One hung, forlorn and pre-tied in my closet, just in case.) I always told myself, “I just don’t like to dress up.” When Shannon and I got married, in 2002, I wore the Campbell-tartan kilt that Mom had bought me.

I knew cocktail attire meant more than jeans and less than a tux, but that’s as far as I’d gotten. Then, the most surprising thing I’ve ever uttered, it just popped out.

“Well,” I said, out loud, to nobody in particular. “I don’t know what cocktail attire is, but I know what a cocktail dress is, and if I had one, I would wear it, and I would be adorable.”

Some people describe the revelation of a big idea or perception shift as a lightbulb going on in their head. This was not that. “Cocktail dress” was a flashbulb. One instantaneous burst of illumination, and then back to the dark, an afterimage seared into the eye, fading almost immediately.

I blinked. I scrunched my brow. “Wait, what?”

I was genuinely and deeply surprised. I did not own a dress. Or anything that might be thought of as women’s clothing. I had unisex trapeze tights, sure. But… wearing a dress? To a work function? Absolutely crazypants.

I went to the party in a sport coat and slacks with this unfamiliar notion rattling around in my skull. I mentioned the idea to a my colleague Victoria.

“You totally should have!” she said.

I shook my head vigorously. “No way. I don’t have a dress, or anything to go with it, and anyway, I am not a crossdresser.”

I went home and couldn’t shake the thought. Where on earth did that outburst originate?

The flashbulb thought of wearing a dress continued to reverberate the day following. I kept wondering where that idea came from. Sure, I’d worn dresses as costumes when I’d attended performing arts camp. I even did a drag act once and that was totally fun. But one drag outing didn’t make me see myself any differently. This did.

And then, pop, I remembered.

A vivid memory came to me, flooded me. It was 1978. I know the year because fourth grade was the age at which the school district mandated long pants for boys. Mom was sending me out into 95º Texas heat in brown corduroy. The material would saturate with sweat and stick to my legs. I hated corduroy.

In the memory, I was walking to school. The morning was already warm and muggy. I was about forty yards behind three of my girl classmates wearing colorful sundresses. I liked the colors, envied the bare legs and loose fit. I had a thought: “I want to wear a dress too!”

Some other part of my brain responsible for keeping me alive took immediate notice, and announced, “That is about as unsafe an idea as you could have. You would be ridiculed, ostracized, possibly beaten, maybe killed. You won’t act on it, you won’t talk about it, you’d better not even think that again loudly.” I buried the notion.

I mean I buried it deep. It had taken forty years to resurface.

I had often joked about being “in touch with my feminine side” or “a lesbian trapped in a man’s body,” but never put two and two together. What did it mean? What was different now?

Did I still want to wear dresses? If so… where? When? I didn’t have answers.

I kept asking questions for three months without acting. I hadn’t confessed this secret to anyone, not even Shannon. We rarely saw each other. She’d come home from working the Sunday Hamilton matinee, we’d have family dinner together; Monday evenings she spent with our teen, Jayden. Tuesday mornings she left for her work week. I never figured out how to raise the topic. “Hey honey, I have this weird impulse to wear a dress. Crazy, huh?”

In July, my curiosity got the best of me. I decided to buy a dress. But what kind? Well, “little black dress” was a phrase I knew as a wardrobe staple. How about one of those? I went shopping on Amazon. I looked at thirty, forty, fifty dresses. One caught my eye: an “A-line skater dress” that had nice shoulder straps, and didn’t seem to require a big bust to sit well. Crap, what size am I? I thought. I had to go swipe a costumer tape measure from Shannon’s room downstairs. My measurements didn’t align with a single size of this dress, but I estimated I was a size ten. For this garment, a medium. I pushed the Buy Now button.

Three days later, I stood in front of the full-length mirror in my bedroom. I felt a mix of thrill, anxiety, and genuine curiosity. What was I doing? What would it feel like? I slipped my arms underneath the hem and hoisted the dress over my head.

Getting the zipper up by myself was a struggle. I was too shy to ask Jay for help, and Shannon was in SF. I pushed the zipper up with one arm folded behind my ribs, then switched to my other hand reaching down the back of my neck. I lost myself for a moment in the mechanics of it.

Then I saw myself in the mirror.

OH MY GOD, I thought. I LOOK AH-MAZ-ING! IT FITS PERFECTLY! I LOVE THIS.

Euphoria flooded me. I spun around and watched the dress flare.

And then the panic set in. What the hell was I doing? Am I a… crossdresser? That word didn’t feel right. I groaned in confusion.

The initial surge of emotion ebbed, and reluctantly, I unzipped myself. Found a hanger, and hung the dress in the closet.

During the next two months, I didn’t put on my dress again. I would go to the closet each day to pick out a shirt, and get a small thrill seeing the dress hanging there. But that was it. I certainly wasn’t going to wear it out in public.

At least, that’s what I thought.