Dressing in drag for Halloween

The only time I dressed up in drag for Halloween, I came to the disappointing conclusion that I was not glamourous as a woman. Sure, I felt pretty on the inside, but as soon as my friend who applied my makeup had me look into a mirror, it became obvious that I would need to reconsider my drag strategy. Some people can transform quite easily into the opposite sex, and some folks struggle. Let me put it this way: I jumble and fumble so much as a woman that I drop the proverbial gender ball — so to speak.

While I’ve always been intrigued by how Halloween often gives folks the opportunity to cross-dress without the fear of being labelled a cross-dresser, I’ve usually eschewed such costumes for more eccentric choices. While other men I’ve known have dressed up as Dolly Parton or slutty Catholic schoolgirls or waitresses from Hooters, I’ve paraded around like “Existential Angst” and a K-Mart inspired “Blue-Light Special.”

Part of me wonders whether it’s a fear of my inner fairy or whether I’ve just been exposed to far too many grotesque gender caricatures and big-titted misogyny that has kept me from dressing in drag for most of my life. Perhaps it’s even as simple as knowing it would be hard to find a dress that fits. Whatever the reason, the one time I did do Halloween drag I was dismayed to realize that by inserting a beat-up copy of a Gideon Bible into my hands I became a shoe-in for some of the older women who I remember teaching Sunday school when I was a child.

I have seen some scary Halloween costumes over the years, but no amount of fake blood and guts could ever scare me more than how much I looked like I should be instructing young children to sing “Jesus Loves Me.” I still have nightmares.

I hadn’t thought about this incident for many years, until I started to have dreams about dressing up as Republican vice-presidential candidate Sarah Palin for Halloween. Actually, I think my dream was really about me dressing up as Tina Fey dressed up as Sarah Palin, only I’m an older and larger Sarah/Tina who gets pulled around a nightclub on a makeshift sled by a bunch of twinks dressed up as huskies. (I have an active imagination.)

I had no issue with this dream or its implied costume choice until I realized that the music playing in the nightclub background wasn’t a typical dance track or gay anthem. Unfortunately, the song playing was once again “Jesus Loves Me” and it immediately made me think back to both my Sunday school years and that awful Halloween party when I desperately wanted to be glamorous, but instead I spent the entire evening talking about sin and reading out passages from my Gideon Bible.

I’m not sure what this all means other than I will not dress up as Sarah/Tina this year, but I ask those of you who do to please dedicate a little of your glamour to me. And promise me that if you attend two Halloween parties this year to save your beehive wigs for the next night when you can dress up as Amy Winehouse. The economy is on shaky ground and we should all think about recycling our costumes.