There is a reason transwomen love Halloween, at least up to a point.
Halloween is the only time we can expect social affirmation for our trans expression.
This is exciting and fabulous until the point where we no longer are willing to see our trans expression as some kind of costume, something that we put on.
At that point, Halloween turns into hell night, because whatever we choose to wear, people tend to see our costume as being a guy-in-a-dress, erasing our trans nature into our costume. We may have a great Marie Antoinette look or a fabulous rock chick, but it all gets reduced down to “dude looks like a lady,” and the fun just is drained out of it.
I have been reading a crossdresser blog that wants their followers to go to the office as “working girl” on business Halloween, the working day that lines up with Halloween. To the author, it’s just so affirming to show up once a year in 4″ Liz Claiborne heels and an outfit from Dress Barn, because Halloween is the day that expression can be affirmed as costume.
I remember all the Halloweens that I wanted some kind of commercial affirmation. I would pay for a makeover, get my make-up done at a department store, have a wig trimmed at a hair salon, anything where I might get some positive feedback for how good I looked, how amazing my transformation was, how brave and witty I was.
Of course, very little of that affirmation had much to do with trans. Instead it had a great deal to do with the wit and smarts of women in the beauty business who know that they are selling affirmation. No woman goes to a salon to leave without at least a few ego strokes.
Now, I may think I look good, but I remember a dance where a lesbian thought I looked like a local comedy drag queen and a crossdresser just laughed and agreed with her, even as I squirmed and showed my displeasure with the comparison.
If the crossdresser had been a girlfriend, of course, she would have seen my discomfort and back peddled, saying I had my own unique beauty or some such, but this was one of those CDs who you can never trust to watch your purse; they just have zero training in how to be a good girlfriend.
Looking for parties this Halloween, just some place to find someone with wit and smarts, an event which might echo the best of my old memories, like making out under the taxi stand or being fed drinks by the goth bar owner and her bartender, well, the chances of that happening again are near enough to zero.
I know why crossdressers live for the affirmation of Halloween.
I also know why transwomen fear the erasure and diminishment that comes with it.