Ian Thomas Malone Does Not Hate Halloween

ITM was once dumped for not caring about Halloween. She would like to correct the record, along with some perspective on the holiday as an unmarried woman in her thirties.

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When I was in kindergarten, my Catholic school hosted a “Wear your pajamas to school” day. This confused me a lot as a child. Pajamas are for nighttime. School is for daytime.

Like many Catholic traditions, I wanted no part in this sorcery. My best friend at the time didn’t either. My mother called the school and told them that ITM & friend were opting out of that bullshit. The school responded by attempting to exclude us both from the class picture to mark the occasion, but unfortunately for them, my mother was one of our “class parents,” and insisted that we were both included. Take that, Roman Catholicism!

Some fifteen years later, away at university, I softened my embargo against pajamas in class. Boston winters are very cold. I had a tiger-print onesie that doubled as pajamas and as a Halloween costume that I wore for three consecutive Halloweens at college, first as Hobbes, second as Tigger, and finally with no obvious designation.

Why the change in attitude? I wish I knew for sure, other than the obvious answer, that a young ITM was a rebel in need of a cause. School-sanctioned pajama days are not the same as a twenty-year-old wearing a tiger onesie because it was cold outside.

My Halloween costume for sophomore through senior year of college. It’s a little big on me now, but still very comfortable.

I look back at the kindergarten saga as the origin of my troubled relationship with Halloween. You see, many people are free to hold apathy toward Halloween. The gays? Apparently not so much.

Last Christmas, I told a story about how I was dumped on December 21st, a few hours before a flight home. A four-year relationship coming to an end so close to the big holiday is the stuff of a Hallmark horror movie, but Christmas wasn’t cited in the long-winded breakup chat. My partner of four years had her sights on a different holiday.

People laugh when I tell them that my longest relationship ended in part because I do not care enough about Halloween. It’s pretty funny. I have nothing against Halloween, but indifference is apparently a big enough crime to warrant the end of a relationship.

Maybe it makes sense. Southern California loves Halloween. All the theme parks have special Halloween events. I live down the street from the Queen Mary, which hosts the popular Dark Harbor event each year.

Before we proceed, it is worth clarifying the exact nature of my feelings toward Halloween. I work from home. I have no children. I have an apartment that is comfortable, but not exactly big enough to dedicate lots of space to seasonal decorations. I have socialized on each of the past three Halloweens since social distancing mandates were relaxed. I wore a costume for two of those social outings.

Is this the portrait of a Halloween hater?

That ex and I also had a fun Halloween tradition appropriate for our ages. My apartment in downtown Long Beach is only a few blocks away from several nightclubs that are pretty much only busy on weekends or holidays. Not being much of a drinker, I used to enjoy patrolling downtown on Halloween, admiring the lines of drunk people in scantily clad outfits, in search of something called fun.

Three Halloweens ago, after that ex and I broke up, I found myself in our local lesbian bar, where the bartender was constantly ringing the bell and dropping candy all over the counter. He had good candy, too. People sleep on the Tootsie Roll. It’s a wonderful treat.

After consuming many whiskey-sodas, my inner sweet tooth had taken over. I asked the bartender if it would be possible to have more candy. He disappeared for a moment and returned with both his hands behind his back.

He asked me to pick a hand. Being a southpaw, I picked the left. He dropped a big pile of candy in front of me with his left hand, then dropped another big pile with his right. It was one of the happiest moments of my year. How can someone who hates Halloween experience such joy, from Halloween?

Last year, I wore a Harley Quinn catsuit to the Aquarium on Halloween.

I entered into a relationship this past spring with another lesbian, known to many of my followers as Eleanor, who cares so much about “spooky season” that it’s listed in her Instagram bio. I learned this fact on our first date. Not being a big secret keeper, I came clean that I’d developed a reputation, among some homosexuals, as being anti-Halloween.

Eleanor laughed and asked me why I’d attracted the perception of being anti-Halloween. I desperately wanted to have an answer for her, and maybe even myself. This season is apparently very important to a lot of people, not just lesbians. I managed to deflect any concern by vowing to participate in a couple’s costume if requested, and to bring ample enthusiasm. We sadly, though probably for the best, didn’t make it that far.

Last week, I was in my building’s elevator with a small child and his nanny. The kid was wearing a Toy Story shirt. After noticing him eyeing my skateboard, I asked him how old he was. He said he was four. I told him I was four when Toy Story first came out, a concept I’m not 100% sure he understood.

His nanny told me he was being Buzz Lightyear for Halloween. His face lit up as I told him that I, too, was once Buzz, and Woody the following year. He said that girls weren’t supposed to be Buzz. I don’t think the four-year-old spends much time on the internet, but a quick Google search for “Sexy Buzz Lightyear” quickly dispelled that myth.

I asked my mother if she had any old ITM Halloween pictures. Pre-transition Ian really hated having her picture taken, but this smile actually looks fairly genuine.

This Ian liked Halloween. But Halloween has something for children. Candy, yes, but also a much-needed deviation from the norm. Halloween was a chance for one day to not be like the others.

Now, at this point, you might be wondering a natural question. Is Ian’s problem with Halloween related to being trans? Not every emotion in a trans person’s life is rooted in their identity, but there are forces at play with the spirits of Halloween that might make things hard on a person grappling with their gender identity.

I’ll admit, I’ve had some fun with this question over the years. When people have asked me if I’m doing anything exciting for Halloween, sometimes I’ve opted for a dark route if I had nothing special planned. Not many people find it funny when a trans woman tells them, “I wore a disguise for twenty years,” but I get a kick out of it. People say you shouldn’t laugh at your own jokes, but I think about the oxygen mask on an airplane. You have to amuse yourself before you can make others laugh.

Was it tough seeing all the girls costumes when I was little? Less than you’d think. I used to like to wear that Buzz Lightyear Halloween costume on days other than October 31st. Halloween costumes are not really built for heavy wear. It wasn’t long before the costume needed to be retired.

I wanted to be a princess more than I wanted to dress like an imitation of one. Princess is a state of mind, one I started to learn before I transitioned. “Princess Ian” was a nickname in multiple friend groups, usually because I didn’t like to help with anything that involved manual labor.

I studied abroad in Australia in the spring of my junior year of college. The mattress in my room was quite crap. I found out that you could fill out a form online for a new one, which arrived during my second week at my new university. When the moving crew brought the mattress, I summoned my new friends and brought them outside, where they all carried my new mattress up the stairs while I held the door. There was a lot of grumbling about “Princess Ian” that night, but I was too comfy in my new bed to care.

When my sister was little, she often liked to dress in full princess costumes in the middle of the summer. The one openly gay lifeguard at our beach club used to get so excited when she’d show up in her full outfit. I suppose if I’d been assigned the correct gender at birth, I might have done something of the same, but I am content that my princess origin story took a different route.

Where I do look back with some longing actually does pertain to the Halloweens of my college years. There are many jokes about college-aged women and Halloween, mostly centered around freezing in New England temperatures in the skimpiest outfit imaginable, with no jacket to be found.

At least at Boston College, there existed the belief that if a woman should engage in an overnight hookup on Halloween, she should return home the next morning wearing her costume with pride, not carrying bits and pieces of it, along the road sometimes referred to as “The Walk of Shame.” There should be no shame, unless of course, one were to carry their fairy wings instead of wearing them.

When I was dumped over my perceived apathy toward Halloween, I became single for the first time since the very first year of my medical transition. I finally got to play the field for the first time in my adult life, with the body I’d always wanted. From 2022-2023, I embarked on an odyssey affectionately referred to as my “ho phase.”