Last night I took my son trick or treating. I imagine that many of you will rightfully censure me because of my reluctance to take a hard-line against such an open embrace of goyishe culture, and it's not that I don't agree with you. I say no to treif food, to TV on Shabbat, to all kinds of things. For my family, I draw all kinds of lines. But this happens to be one line I am not willing to draw.
I grew up being sent trick or treating with friends while my house remained dark. For some reason, I see this as a compromise that is more stigmatizing than a real choice. To me, it said, "We will let you celebrate this ridiculous holiday, but don't want to be seen as endorsing it ourselves."
But today, I choose to let my son celebrate Halloween because I don't want to live in that divide, and I don't want to raise a child to be doubtful about where he stands. In this world of being able to be both and both, of whatever category that is, a little bit this and a little bit that, I want to make a clear statement that it is excellent to be a model of integrity regardless of what kind of Jew you are, what kind of community you belong to, and what kind of person you are.
So we gave out candy that was all hechshered, we went only after Shabbat was over, and we did not dress up in any way that would glorify death or violence. If I'd have been gutsy, I would have handed out little UNICEF boxes or something to help kids collect for UNICEF (but I'm not sure if that's done anymore?). We also ended the evening at a special Halloween havdallah complete with spooky incantations (brachot) and a flaming kos yayin (wine cup).
I see it as my job as a parent to help my son live a life of integrity. Sure, he's only a few months shy of 5, but if he smells any whiff of hypocrisy, he'll make sure to say it aloud. We make our compromises where we must, and others we embrace. It's this one that makes me feel good that I made it possible for him to be a part of something bigger, something fun, and kept it consistent with my values.