I have a Halloween costume picked out for this year. My roommates and I are going to be Teen Girl Squad. This was the roommate's idea. Now, unlike the roommate, I celebrated Halloween as a child, I used to get dressed up in a costume (generally a dress of some kind, and a crown), put on a coat, grab a pillow case and trudge around my neighborhood asking for candy. It was great fun. I love dressing up. However, as I get older I've begun to worry whether or not I really should participate. Halloween is just not a Jewish holiday.
Besides the issues of devil-worship, and the fact that it was originally Samhain, or all Hallow's eve, Halloween in the modern era is somewhat problematic. It has become, according to many sources, "National Dress Like a Slut Day." Or, as a friend of mine said: "the day where men dress like women, and women dress like sluts." Hurrah. The New York Times explores this trend in terms of feminism, I think for the second year in a row. Or maybe last year they talked about how little girls want to be princesses. At any rate, Gawker seems pretty enamored of the Times' article, and I can't help but agree that the whole thing is ludicrous. Also, dressing like a slut is probably not a major Jewish value. Probably. If it is I need a wardrobe update.
Aside from the issues of sexuality, the observance of Halloween strikes at the core of the tensions inherent in American Judaism. Are we more American, or more Jewish? In this Chabad question-and-answer, they try to straddle that gap by offering Purim as a replacement. Hey, you can't dress up for Halloween, but we have a holiday where you can, and it even has its own cookies! I actually like the answer given there for why Purim is a better holiday, and a better example for children, but it doesn't really help in October. Debbie Schlussel tries to substitute Sukkot for Halloween. You decorate a house, and go from Sukkah to Sukkah collecting candy. This seems a bit more practical: it is closer in time to the competing holiday, and allows parents an afternoon nap on chag while the kids run around eating jellybeans.
One response, quite similar to that of the Evangelical right is to react passive-agressively, or even agressive-agressively. Shifra describes religious children tearing up the Halloween decorations at Six Flags when they were there during the intermediate days of Sukkot. I understand if you don't want to observe the holiday, but c'mon, you live in America. Are you going to tear down Christmas decorations too? If you follow that line of thought then Christians, many of whom think that Christianity superceded Judaism, have the same right to remove any religious paraphernalia that offends them. Of course this assumes that Halloween is a religious holiday, which it may still be to some Wiccans. Or Pagans.
On the other side are Jews who deny that it is a religious holiday and celebrate it, akin to Thanksgiving, either because it is fun, or because it feels like an "American" thing to do. While I wouldn't necessarily attend this party, someone who calls himself "Superjew" is having quite the Halloween party. That particular one is a bit too reminiscent of bacchanals for my taste, but to each his own.
As for me? I'll probably be at the parade in Greenwich Village, with my roommates. Dressed as "Cheerleader." Although maybe I'd have more fun if I followed Jdate's guide for Halloween hookups.