This little boy who fancies hot pink dresses and remarkable ruffles and sparkly, pretty things—he makes me giggly and hopeful and wishful that the world could be as evolved as his mama and his daddy, who allow him the indulgence of prancing like a princess not just in the family playroom but out on the playground at his elementary school.

But mostly, he makes me worry. Scared even. And when I’m not applauding her for going all the way hard for her son’s right to just, like, be, I’m wondering just what in the hell was she thinking buying pink dresses, purple tutus and ballet slippers for her son and telling the world he’s a “princess boy?”

A little background: Last year when Cheryl Kilodavis went to pick up her son, Dyson, from preschool, he came twirling over to her in a sparkly red dress and pink heels, super excited by his ensemble. Eyebrows raised, his mother coaxed her kid out of the dress and, the next day, dropped him off at school with some rough-and-tumble “boy” dress-up clothes, convinced that her 4-year-old boy, who liked climbing trees and shooting hoops, chose to dress like a little lady because there weren’t any good boy costumes for him to choose from. Still, when she picked him up from school later that day, Dyson greeted her in a yellow dress. Halloween proved even more interesting when, much to his mother’s chagrin, Dyson announced he wanted to go trick-or-treating dressed like Cinderella. His mother relented only after Dyson’s big brother, Dkobe intervened: “Mom,” he said. “Let him be happy.”

A few teacher meetings and a psychological evaluation later, Cheryl embraced her son’s happy and started buying him the pretty things he craves: clothes that are pink and sparkly. And she wrote a book about it—”My Princess Boy”—with the hope that it would help her son’s classmates accept him for who he is—a five-year-old boy who likes to dress up like a girl.

I can dig it. Dyson is a lucky little boy who has parents who love him for exactly who he is, no matter how much he bucks society’s gender rigidity—no matter how much criticism and ridicule he faces for dressing like a girl and they face for letting him. After all of the Willow Smith “Whip My Hair” brouhaha a few months ago, I was one of the first to remind folk that she’s just a kid and has the right to express herself by coloring outside the lines, no matter how uncomfortable her mohawk, leopard print leggings and auto-tuned lyrics make us.

But raise your hand if, after hearing his story—or seeing The Princess Boy bouncing around in his purple tutu on The Today Show earlier this week—you didn’t cringe just a little for Dyson. That you didn’t automatically conjure up in your mind an image of him being snatched from the monkey bars, surrounded by a gang of Billy Badasses and taunted and pummeled to a pulp for being a cross-dresser. I mean, my God, didn’t we JUST come through a tough couple of months grappling with the suicides of a grip of students—some as young as 10—after they were relentlessly bullied for being or suspected of being gay? And while his parents take all the public pats on the back for their saint-like special brand of tolerance and acceptance, don’t you feel just a little bit like they’ve set up their son for a whole lot of ‘splainin’ he may not be ready, willing or able to do? Get a gander of little Dyson posed all sassy in his fancy frocks and it’s no great leap for people to peg him effeminate and innately gay. Or to assume he will be after spending years in tutus, pink tube socks and ballet slippers. But what happens when Dyson turns seven and decides girlie is so 2011 and he wants to wear sagging pants and Tims to school? Who makes that hard turn for him? And, more importantly, who stops The Mean Ones from reminding him on the soccer field and later in the football locker room and at his summer job and in his dorm room that he was the cross-dressing kindergartner all over YouTube, the Twitter, and the highest-rated morning show in the media capital of the world? I’m sorry, but as a mother, I really can’t understand the mindset of a mom who would put her kid in that kind of physical and mental danger.

Putting that boy on the school bus with some pants and a t-shirt is about setting some boundaries—about affording her son some self-preservation until he’s able to handle himself when the bullies, knuckles dragging, come for him. Let the boy wear his tutus and rubies—at home, where he is protected and safe from the judgment and bullying of others and he can be reminded, constantly reminded, that his parents love him and are passionate about his happiness and think it more important that he learn how to be, first, in the comfort of his home at the hands of his capable parents and supportive family and friends, before he hurl his bedazzled little self into the middle of the nasty, cruel world that still cuts and bites and spits out different.

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  1. I agree. And I do have this immense heartache because he is growing up in a society where the behavior, attire, and even interests for men are stricter than those for women. Halloween is the one day of the year where you can be anything else than what you really are and it should be a safe holiday for boys who like to dress up in dresses to do so without being patronized. Sadly, even Halloween costumes are gender assigned. As more people come out about breaking subtle and overt gender roles, transgendered individuals become more vocal, and people become more accepting, it’s still not enough universal understanding to embrace little Dyson should he continue to wear dresses or if he outgrows them.

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