Karen, a mom from Sam’s school, emailed me after my recent blog post about our head of school dressing up as a woman for Purim last week. Karen’s son, Jacob—not a pink boy like Sam—dressed as a girl for Purim. Karen felt conflicted about the meaning and effect of cross-gender dress-up. Was it mocking? Was it funny? Was it educational? She wanted to be respectful, and worried that her son might offend kids like Sam.

I told Karen that, in my opinion, well-intended cross-gender dress-up is useful because it furthers the conversation about gender. That sometimes we simply dress up as things we are not—a bumblebee, a giant sponge, Frankenstein. And that sometimes we dress up as things we aspire to be—Superman, Queen Esther, a fairy princess. So I saw her third-grade son dressing as a girl as, if not a desire to be female, a benign expression of pretending to be someone different from his usual self.

Humor often relies on contrast. It’s funny when the head of Sam’s school dresses as a woman, because he is a masculine man. If Johnny Weir dressed up as a lumberjack, that would be funny too, because he’s usually so femme (it would also be a sassy retort to the Canadian Olympics commentators who said Weir should undergo gender testing.)

Above all, humor is situational; intention and audience matter. It’s certainly possible to be offensive if one tries. But Jacob was not dressing up as a girl to make fun of anyone. In fact, I think he served a useful purpose, as the head of school did, in making people momentarily aware of the gender behaviors so ingrained in us that they’re usually invisible.

But maybe I’m wrong. In an interesting post last week on Salon (which you should read for its commentary on the color pink and its plucky reference to “engorged ladybits”), author Kate Harding refers to “the enduring comedic value of a man in a dress.” Is the head of our school in a dress—or Jacob—making a mockery of women, or, more to the point of this blog, of feminine men and boys?

What do you think?