Transcending gender roles, or, When to draw the line?

It's that time of year again, time to sit down and talk about what Owen wants to be for Halloween. Last year he wanted to be Shrek, remember? And I looked and looked for a decent Shrek costume, then when we finally found one, and he was at the pinnacle of 3-year old Halloween excitement, he got sick and spent Halloween night in the ER. So this year, we're starting early, looking in magazines and online for something special that he'll really enjoy. Last night he went through the Lillian Vernon catalog, and he got excited and told me he found what he wanted to be: Dora the Explorer.

So here's my dilemma. What if he really does want to be Dora? Do I care that she's a girl? Do I care that he would have to wear a pink shirt and a long wig? It obviously doesn't bother him. And isn't that what Halloween's all about - dressing up as something you're not? So I'm trying to think what I should do. Should I say simply say okay, or maybe make a subtle statement about finding something for a boy? I think I said something like, "Oh, that's a really cool one! And here's a Diego costume [Dora's boy cousin] right next to it! Do you like that one? I bet we could find some really cool boy costumes in here!" And I turned the page, and before you know it, we're moving on to a Cat in the Hat costume that he thought was super cool. So maybe I can lean him that way (except maybe not, the price is ouch). But if he pushes the Dora issue, I don't know what I'll do. It doesn't bother me, I don't think, but I hope he forgets about it! (He doesn't really have the skin tone for black hair, anyway.)

Tonight the boys were laughing about something, hysterically, and Owen doubled over onto the bed and yelled, "I'm dying my head off over here!" I thought that was an interesting combination of phrases (presumably the love child of laughing my head off and dying laughing).

Now that I'm thinking back to past Halloweens, I can't forget about this one. What a cutie. I still have that costume; we're thinking about putting Ari in it this year.

Now Ari, that one could pull off the black hair.