What's a Jewish Cougar supposed to be for Halloween?

Jews aren’t supposed to “do Halloween.” When I was in Hebrew School, the principal sent out a memo telling parents that it’s a pagan holiday and therefore not proper for “the children of the Hebrew Academy” to dress up like goblins and witches. What a bummer! I still managed to collect tons of snicker bars and eat them.

But now that I’m older, single, and living in Manhattan, it is my duty to partake in the fun of dressing up, being stupid, and having an excuse to talk to whomever. It occurred to me that maybe it’s also an opportunity to mask parts of myself. A chance – for a change – to keep some information a secret in a social setting, at least for one evening.

I don’t know what the plan is yet. Downtown Manhattan on Halloween is one big circus so you don’t really need a destination. All you need to do is ask a guy what he is supposed to be (even when it’s obvious)…an insta conversation starter. The only problem is, you have no idea what the guy actually looks like naked (of his costume) or in broad daylight. But who cares? What’s beneath the superficial disguise doesn’t matter. After all, it’s Shalloween!

My costume this year? I was thinking of purchasing some cat ears (and some cleavage), wearing a Jewish star around my neck, and going to Toys R Us to buy a boy toy I could put in my pocket. Hilarious! Not. But then I realized, after all my moaning over how to remain semi anonymous with this blog when I’m meeting guys, dressing up like a Jewish Cougar is probably not a good idea (nor does it qualify as a disguise).  So instead my girlfriend and I are going to be “The Girl with the Dragon Tattoo” and “The Girl who Played with Fire.” Basically, that means I get to dress up like a hot lesbian. Not sure what this says about me, but I already have the appropriate attire hanging in my closet.

Or, maybe it’s my chance to flirt. Not only with dudes.  Maybe I can try what all the guys in my office have been saying: “Cougel, forget men! It’s obviously not working for you. Maybe you should be a lesbian!”

I don’t know if that’s feasible; if I can actually try to be one when I’m not. But on Halloween, maybe I can pretend.