Christian arrogance, bumblebees & butterflies, a sad loss, and a drag queen goes to law school...

Dear Prudence:

I am the father of a bright, artistic, and thoughtful 5-year-old boy. He enjoys playing dress-up and, from time to time, putting on his mother's shoes or jewelry and declaring that he is a girl.

Recently, when my wife and I asked him what he wanted for Christmas, he told us he wanted a skirt so that he could be a girl. We weren't sure whether he was serious, but when he saw Santa at the mall, he very earnestly declared that he wanted a skirt. Since that time, he has written several letters to Santa, and in each he has asked for a skirt. (As an aside, we gladly let him dress up as the Wicked Witch of the West for Halloween, which provoked some stares and insensitive comments, to which he was thankfully oblivious.)

While we want him to be his own person and be comfortable in his own shoes (ruby or otherwise), my wife and I aren't sure whether to honor this request, as he undoubtedly will want to wear the skirt outside of the home eventually, which leads to a series of difficult conversations that we aren't prepared to have with a kindergartner. Yet we know he will be heartbroken if Santa does not bring him a skirt of his own.

—Conflicted at Christmas

Dear Conflicted,

How lucky that your son has parents such as you, who will adore him, ruby slippers and all. It's too early to know for sure where his desire to dress up will lead. But studies show that little boys with a persistent interest in wearing girls' clothes, and who have other nonconforming gender behaviors, have a strong likelihood of eventually identifying themselves as gay. If that is the case for your son, when the time comes for him to come out, happily for your relationship with him, it will come as no surprise.

My colleague Hanna Rosin's fascinating piece about these children makes the important point that the vast majority are not transsexual. To the concrete-thinking mind of a 5-year-old boy who likes typically girly things, saying he's a girl is a way to express this interest. I spoke with Catherine Tuerk, co-founder of the Gender and Sexuality Development Program at the Children's National Medical Center. She said it's very important that you have a talk with your son because you've got reassuring news to tell him: that although he may suspect he's the only boy who feels the way he does, actually there are a lot of boys like him, and as he gets older, he will make friends with many of them. Explain to him that there are different kinds of boys—he's a boy who's interested in things girls also like, and that's terrific. You can tell him some boys act more like bumblebees, some like butterflies.

When he opens his present, he will see that Santa heard his plea and delivered a skirt. But Tuerk said you need to have another conversation, one that's going to be a little harder, about the skirt. You have to explain to him that not everybody understands how many different kinds of boys there are, and so if he wears his skirt to the playground, or to school, there are going to be people who say mean things or make fun of him. Tell him you want to figure out the places he can wear his skirt—at home, maybe grandma's, etc.—where he can enjoy it and feel comfortable. This conversation is not about conveying shame, but about giving your child good options, and not locking him into a limited identity ("The boy who dresses like a girl!") with his classmates.

As Tuerk points out, often as these boys get a little older the intense desire to dress up wanes, and they find other avenues—art classes, theater—to express their interest in beauty and fabulousness. There are many conversations ahead for all of you, and at the CNMC Web site are materials on childhood gender issues, book suggestions for you and your son, and information about support groups. Talking about your bright, thoughtful, artistic son with other parents of similar children will benefit you and your darling butterfly.

—Prudie