Halloween | Dear Baby Maybe #18

Dear Baby Maybe,

Ah Halloween. A time to dress up. A time to be spooky. A time to carve pumpkins and drink cider and ... yeah, I hate it all. I’m not a fan of Halloween. I have a Cookie Monster beanie I bring out in order to play along without having to put in much effort. But honestly, we’ve had some interesting times when we were dressing up for Halloween.

In your junior year of High School (while you still think you’re a straight boy) our mom will come home one day with a Halloween idea. She bought a wig for you to be Amy Winehouse. Our mother, who raised you to be a boy, comes home with a long black wig styled with a beehive so that you can dress up as Amy Winehouse for Halloween. She’ll then take you shopping for a dress, and for heels, so that you can complete a look. She’ll contest that Amy would probably be seen in a tank and jeans but you push back, reminding her that many people see her done up for award shows and that’s the Amy you want.

This will be our first real moment of presenting our femininity to the world, although we won’t be able to admit how much of it feels right for us. But somewhere deep inside, we’re planning ahead. We wanted an outfit that we could try for the sake of costumery. But we got a reason to buy a dress. We got a reason to get heels in our size. I’m actually pretty proud of the fact that we were able to ask for and get the things we wanted at that time. I still wear those shoes. I still have the dress in my closet. A magical part of discovering our identity so late in life is that I haven’t outgrown my first dress. My first pair of heels still fit. I can revisit the strength of 11th grade Maybe whenever I put those on, and feel the resilience they brought us.

Now, remember, this was before we had any words around gender and sexuality. For the purpose of where we were at the time, this was a “drag costume” and it was largely comical for people to see me dressed like that. Telling people I was a boy, a straight boy at that, wearing a dress and heels on Halloween made for a few good laughs, which helped to solidify the idea that femininity was not something I could seriously live in. We would be mocked if we wore those shoes constantly. Wearing that dress on any other day would not make sense. You’ll get flooded with messages around when you’re allowed to break the rules, when you’re allowed to wear a “costume.”

Before the next Halloween, we’ll come out as gay. Still unaware of words for gender feelings, we’ll be calling ourself a gay boy. And that Halloween, we’ll go as Batman. That’s right. The last Halloween I thought I was a straight boy I went as Amy Winehouse, and the first Halloween I knew I was queer I went as Batman. To be fair, it was a couples’ costume because the boy I was crushing on at the time went as The Joker. We never got into comic books and superheroes, but we’ll go to Hot Topic or something and buy a Batman T-shirt and wear a black cape that we already had for some reason. And though the dichotomy of those two costumes is just as ironic as Halloween costuming gets for us, I think it’s a perfect interpretation of how we really never fit into any box, and largely seem unaware that there even is a book of rules.

I know this sounds fun and cute and you’re probably wondering how I got so bitter about Halloween. All I can tell you is that as you grow up and into yourself, you will notice how people respond to the way that you dress. You will remember the laughter of the Amy Winehouse costume, and feel that same response as you journey into more feminine outfits. But notice the difference between costume and outfit. To me, my wardrobe is to make outfits. But too often my wearings are seen as costumes. I guess I just got bitter about being seen as fake and “dressed up,” so I have harbored a generalized distaste for participating in any extreme ways anymore. For now, Halloween is not my thing. For you, Halloween is a chance to explore. So use it. Break the rules. Buy your costumes that will become your outfits. You’ll be able to just call them your clothes soon enough.

Your Future,

Maybz