Seeing ‘The Parent Trap’ as a Closeted Transgender Teen

The 1998 Parent Trap remake is a touchstone of the cinematic radar for countless millennial ladies now trudging into adulthood. You likely remember the ascent of the now fallen-angel Lindsay Lohan, or recall being wowed by Disney magic turning a single tween into twins. What I will never forget about The Parent Trap — as a deeply closeted teenage transgender girl — is weaving a convoluted parent trap of my own just to see it.

Changing your gender at age 13, right after telling the world I was a man at my bar mitzvah, wasn’t a thing people did in the ‘90s (or dared publicize if they had). Temporary relief from the unwavering gender dysphoria I felt came mostly from stealing my sister’s clothing and wearing it locked in my bedroom and exploring femininity any other way I could without getting caught.

Enter The Parent Trap.

Having grown up watching the original version my mom taped on VHS, I had to see this one. But I was older now, well aware that some movies were marketed to girls and I wasn’t exactly a girl.

My scheme seems simplistic looking back, but it sticks in my mind because of the thought I put into crafting a web of plausible deniability. I was going to convince my parents to let me see a girl movie by framing it through just how mature and responsible of a young man I was.

My little brother Ryan turned 4 in June of 1998. He could just about sit through an entire feature. And I, having survived my ritual receipt of manhood that previous November, was by now getting routinely dropped off with friends to see movies — the ones marketed to teen guys, of course — without parental supervision. So it was decided: I would ask Mom and Dad to bring Ryan to The Parent Trap, on my own, because I was a caring big brother.

I should also mention I had two little sisters who were very eager to see the movie, too. But I was terrified my “wrong” thoughts would expose me somehow. Even just crushing on a girl in front them could have been embarrassing, but this wasn’t just wanting to date a girl, it was wanting to be her. Ryan was too young to pick up anything, so I pitched this on a day my sisters were busy.

Like magic, the plan was a go.

In the film, Hallie and Annie teach one another their quirks as they prepare to switch places returning from camp. Hallie is an easy-going tomboy who plays effortlessly with femininity when she wishes. Posh twin Annie is a natural femme unafraid to get dirty. Tomboys gently pushing gender boundaries were the closest thing like myself in the media I could find.

Deep down, I had faith my parents would try their best to support me — but the further ramifications of acceptance were no less mysterious and scary. What kind of hell would this cause for my siblings? Would they get teased? Might we all have to pack up and move to another state to avoid the local intrigue? This was a big ask over something I was praying just as hard to outgrow one day.

The Parent Trap is about bringing a family together; my fear was tearing one apart. The possibilities were daunting: what if I got sent to a special school — or a crazy asylum for all I knew — over thinking I should have been female?

The movie itself closely parallels the experience of hiding the “wrong” thoughts of being transgender. While both twins are taken for one another at first (except by the Parkers’ growling dog), the deception becomes harder and harder to sustain. Hallie rattles off about California wines in London as Annie panics in fluent French in front of her baffled father. These “It’s almost as if…” moments with friends and relatives chipped at the reveal each girl did not want to — but knew she must — make for their plan to proceed.

It took well over a decade longer before I opened up. My family indeed accepted me unconditionally, as should be the expectation, not the exception, in anyone’s home.

I wish I could tell my younger self how pointless my little “parent trap” was. I worked hard keeping myself contained and hidden, but only once the truth came out did anything actually get better. I did not trap my parents into anything — I had only trapped myself.

Parent Trap Week is an entire week dedicated to the 1998 iconic film, in honor of its 20th anniversary. See all the posts here.

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