Halloween carries scary dilemma for trans people — and a rich history of exploration

If I go as a female character, some might read me as "man in a dress." If I go as a man, I might not be seen as a woman at all.

If I'm a female character, some might see a man in a dress; if I go as a man, I might not be seen as a woman

Lara Rae dons a ranchwoman costume for a Halloween party with her friend Brenda Bookbinder, right, as the ranchman. (David Stambrook)

For a 56-year-old transgender woman, Halloween is a complicated, scary but also nostalgic time of year.

As a young trans child in 1960s Glasgow, I looked forward to Halloween, especially those years when my mother, busy with work, would forgo a homemade costume. My sister and I would simply swap clothes, she in a football jersey and shorts and me in a flowing red pinafore.

As someone who knew she was trans at four years old, those were happy Halloween years for me.

When I moved to Canada and closer to puberty, things got more complex.

My gender confusion was now something secret and shameful. These were the years of trying to fit in.

In junior high on Halloween, boys would ask if I wanted to go downtown and throw eggs at queers. I never did, but this was a thing. 

In tandem with the larger, more famous New York Halloween Parade started in 1973, there was (and still is) a Halloween street event on Church Street in Toronto.

Back then, it was the one day in the year when people could dress in the clothes of the opposite gender without fear of arrest. Harassment was another story, and people, mostly young men, would often head downtown to mock, yell and throw eggs at those exploring gender expression. 

As I moved into adulthood, another spectre hung over the parade: AIDS.

Not only did homophobia and transphobia intensify, but many colourful figures disappeared from the festivities, dead or too ill to attend. Lou Reed's song Halloween Parade (1987) captures that time. By 1987, 9,000 New Yorkers had died of AIDS.

There's this vicious non-caring or, in some cases, a cavalier non-caring under the guise of something else- Lou Reed

Back in Toronto, my costume in those dark years was a mask and cloak of shame.

So much of the free expression that exploded in the '60s was packed up and shoved to the back of the closet. Much of mainstream society had turned its back on the LGBTQ community.

As Lou Reed said, looking back years later: "There's this vicious non-caring or, in some cases, a cavalier non-caring under the guise of something else. It's a complete disregard for the other guy or woman or child, and a complete rejection of any kind of humanity and an unrelieved viciousness for laughs."

As some progress was made both in AIDS treatment and in public attitudes toward gay people, the biggest targets on Halloween became trans people, a trend that continues. Many of the current challenges involve cruel mockery, especially around public trans women like Caitlyn Jenner, who is ridiculed in horrifying Halloween costumes.

Last Halloween I spent most of the day, along with others, reaching out to vendors and filing complaints. Some gains were made and this Halloween the Caitlyn costumes, along with "Manny Granny" (which was already a slight improvement on "Tranny Granny"), seem much less prevalent.

But personally, the biggest challenge for me remains the Halloween party.

Halloween, for some questioning young people, is a somewhat safe way to be gender creative. But for a trans woman like me, who has some masculine features, party invitations come with a great deal of anxiety.

Picking a costume is hard when you're trans. If I go as a female character, some might read me as "man in a dress." If I go as a man, I might not be seen as a woman at all.

Even if I go in a head-to-toe animal costume, my voice is often mistaken as male. 

At the same time, it seems a bit of a scold to demand that men and women don't cross-dress as a costume choice.

Last weekend, I found myself at a party in Ottawa. It's the first time I've attended a costume party since transitioning. The woman I was staying with is a lifelong friend, but she and her partner were the only people I knew.

Unknown to each other, my friend and I both considered whether reaching out to the hostess and explaining my anxiety in advance might help. But I felt it would be too demanding. Should I ask a stranger to police her guests' behaviour? And when alcohol is added, any instructions given on arrival tend to evaporate in the fog of intoxication.

The other problem was that I didn't bring a costume at all. A quick scramble and we did our best. Off my friend Brenda and I went, dressed as man and lady ranchers.

Halloween brings the fear people will think Lara Rae's gender is her costume. (Lara Rae)

The party was fun and the people were kind, but all night some people referred to me with male pronouns.

Later, and with no ill intent, the playlist landed on Sweet Transvestite, a song written for the The Rocky Horror Picture Show, a dated take on gender written by Richard O'Brien, who is an on the record transphobic man.

I knew nobody there wanted to hurt my feelings or make me cry. No costume worn by guests was offensive to my dignity or any other marginalized group.

And yet, twice that night I could be found sobbing in the corner, feeling alone, the only one of my kind in a house full of strangers.

As much as it's not fair, I know these experiences are the growing pains of a whole society in transition. We'll get there. One day for me, all this Halloween heartache might be replaced by a good old fashioned toothache.

And I'll never forget the positive impact this holiday has had on the LGBTQ community.

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Lara Rae


Lara Rae is a stand-up comic, comedy writer and the former artistic director of the Winnipeg Comedy Festival.