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The Princess Diaries

Max is playing a game he calls "vehicle." It's a typical, developmentally appropriate product of a 4-year-old mind in which he races up and down our driveway pushing a variety of—you guessed it—vehicles. It's an altogether unremarkable scene, with the exception of his wardrobe: a mid-calf violet-and-red paisley dress. Velvet, no less.

It's not even his older sister's dress. He'd been borrowing her dresses so often that even though she wasn't wearing them anymore she began to object, so we did what any enlightened but thrifty new—millennium parents would do—we got him one at a yard sale.

It all began innocently enough a couple months back, when an evening of second-floor silliness led Max into his 8-year-old sister Alison's closet and her sparkly red party dress. It was a lovely choice, and we all had a good laugh over it. I think the only reason I was vaguely unsettled was that it triggered memories of being paraded in similar attire through my parents' cocktail parties by my older sisters, for whose approval I once traveled great and humiliating lengths. But the evening turned out to be just a hint of cross-dressing to come.

Alison had a closetful of dresses and was initially delighted by her brother's impromptu fashion shows. At preschool he discovered the joys of the dress-up area, and the girls in his class were tickled pink at first to have a new and novel member of the princess posse.

I only flinched a little the day I came home to find him splayed out on the couch in a floor-length yellow gown with floral accents at the cuffs, flipping through a Minnie Mouse book. A father less secure in his own masculinity might have by then had the poor kid in military school, but I was marginally calm. I'd grown up with three politically astute sisters, and my feminist credentials were solid; I knew that by allowing Max to explore his feminine side I was actually helping him on the road to a more emotionally open and healthy life.

While his desire to wear dresses appeared limitless, his permission to do so was not. We set our property line as the hem of his dress-wearing nation, figuring that while it probably wouldn't bother him to arrive at the local playground in his favorite frock du jour, it might send us into therapy. That worked, until one Sunday when I needed to go to the hardware store, which was about Max's favorite place on the planet. His penchant for wearing dresses had in no way diminished his obsession with tools; he was nothing if not well-rounded.

Max wanted to go, but he didn't want to change. I wanted to go, too, but comparing socket wrenches at the hardware store with my dress-wearing son by my side wasn't exactly the Kodak moment I had in mind. I thought seriously about making him choose: hardware or women's wear. But I was too tired to win the argument that would follow, and besides, like many parents, we try to help our kids withstand the pressures of small-minded, mean-spirited peers. Now it was time to show Max that I didn't care if strangers thought me odd for breeding a cross-dressing 4-year-old. So off we went, me in jeans and a sweatshirt, Max in purple velour.

The first couple of humans to notice him happened to be men, and their initial response was the benevolent smile accorded to little children. Then they noticed what he was wearing under his green winter jacket, at which point their faces froze and they slipped quickly and shamelessly into the nearest aisle. Women reacted differently. They began with the "Isn't he darling" smile, then burst into full schoolgirl giggles of delight as they spied what he was sporting.

Then Halloween rolled around. While Alison had nailed her costume and was out looking for a bag big enough to hold her candy dreams, Max was vacillating between Bob the Builder and a dinosaur. My wife sensed something was up, so she gently confronted him about it. Under the yoke of sincere maternal concern, Max cracked. He admitted what he really wanted to be for Halloween: a princess.

We were now in uncharted waters. Max was threatening to turn that most sacred of pagan, chocolate-smeared holidays into a nightmare of parental explanation. How could I possibly spin this into something that didn't make me look like a really big wimp? The answer was I couldn't, but as my wife has taught me, in cases like these, it's not about me. We had gone too far to turn back now, and besides, one of the ironclad laws of childhood should be that Halloween costumes are the sole choice of the wearer.

So when the night of a thousand neighborhood kids rolled around, Max rolled out in a pink princess dress and silver tiara. At every house, Max stayed for a minute or two to chat up the candy donor. When I put him to bed many hours later, I asked him what he was talking to everyone about for so long. "Oh, some people thought I was a girl," he replied, without a hint of self-consciousness.

I think after the novelty of that very first night of borrowing Alison's clothes, Max kept it up largely because dresses got him a lot of attention. But after a while the attention either dissipated or turned sour. One day he dressed up at school and was promptly ostracized by playgroups of both genders. Last night it dawned on me that he hadn't put on a dress in at least a month. And so another in a seemingly endless series of childhood phases has slipped almost unnoticed into the next; now all he wants to do is play basketball.

With the benefit of hindsight, I think we handled it pretty well. We didn't overreact (at least not in front of Max), the most natural yet perhaps least effective method of handling such situations. When we were in the middle of a stage that pushed our biggest, most sensitive buttons, it was hard to imagine there might be light at the end of the tunnel. But allowing him to cycle through largely on his own shortened the stage's duration and lessened our own pain. With our support, Max discovered he loved wearing dresses for a while, then didn't. Along the way, we all learned some valuable lessons about patience, tolerance, and fashion. Still, I have a feeling this next Halloween is bound to be a letdown.

Jonathan Kronstadt is writing a collection of essays about his life as a stay-at-home father.