15 Crushes and the Art They Gave to Me

Since the age of four, I’ve had approximately 7,206 crushes. And I’ve watched so many movies, read so many books, and listened to so many songs because of those crushes.

Art is not simply an easy source of small talk. The work that speaks to someone can say so much about who they are. Listening to a song your crush recommends is a low-stakes window into their identity. It’s a way to get closer to someone, away from them. And isn’t that what a crush is all about? A solitary experience that has everything to do with the other person and at the same time nothing at all?

Often after the crush fades the art remains. A new favorite movie, an author to continue obsessing over, a song to put on every playlist. Or I might look back and laugh, reflecting on the person I was trying to be. Like did I really watch all three Rush Hour movies in one day for the love of my middle school life? I sure fucking did.

When you’re gay and especially when you’re gay and trans your crushes have as much to do with who you want to be as who you want to be with. My whole life I felt like if I could just find the right girl then I wouldn’t have to be one. I wasn’t aware that’s why my crushes were so strong, but in retrospect I was displacing my gender feelings onto the people around me. I think that’s why I had so many crushes on my sister’s friends. My sister is four years older and spending time with her friends offered me a window into the different types of girls I could someday become. The different types of girls I wanted to become, the different types of girls I feared I’d become.

Here are 15 crushes and, more importantly, the art they gave to me — starting, of course, with one of my sister’s friends.


1. First Crush: Avril Lavigne

My sister’s elementary school best friend and my first crush is gay, and she was gay the entire time I knew her. She wasn’t out of the closet, but you can just tell sometimes. She was a classic tomboy who looked like a skater. But despite her cool exterior she was always so kind. She made me feel included all the years she and my sister were friends and all the years I crushed on her.

When Avril Lavigne burst onto the pop punk scene in 2002 looking like a Hot Topic incarnate, my crush was an immediate fan. Everything my crush liked, I liked, and Let Go became the first album I listened to on repeat. I didn’t understand Avril’s angst (or her fashion) but I wanted to. I wanted to so badly.

2. 3rd Grade Bully: The Sammy Keyes Mysteries

When 3rd grade began and a new student arrived I was immediately smitten. She seemed to like me too. We spent the first week of school becoming friends. But then someone in the cool group made fun of her for liking me. She started bullying me to prove this wasn’t true. The rest of the group joined in and our teacher noticed.

I didn’t want my crush to get in trouble, so I denied my teacher’s observations. But she knew. And she took pity on my mostly friendless self. She recommended me book after book, recommendations I graciously accepted. My favorites were the Sammy Keyes mysteries, a sort of modern take on Nancy Drew where the girl detective has some added snark. I devoured the first seven books (all of them at that point) while the bullying continued, as did my crush.

My real love that year was Sammy. I saw myself in her loneliness, her intelligence, and her endless self-destruction.

3. Middle School Best Girl Friend: Rush Hour Trilogy

Middle school was when I felt most like a boy. I continued to connect with girls, but they no longer connected with me. They were too busy with fashion and makeup and boys, with breasts and bras and periods, with uncontainable emotions and everything else that puberty wrought.

Except one. She was going through all those things, but she liked me. And I liked her. We became best friends and I had a crush on her throughout 6th and 7th grade. I wasn’t always included in her girl activities, but I spent every minute with her that I could. She was the best connection to girlhood that I had.

The summer between 7th and 8th grade I started to feel her drift away. So when she invited me to go see Rush Hour 3, I quickly said yes. I hadn’t seen the first two but I pretended like I had and quickly did a double feature to live up to my lie.

They’re terrible movies. And she spent the whole night giggling with some guy she also invited. Four and a half hours of bad martial arts comedy just to be reminded that I was a boy and she was a girl and our friendship was slowly ending.

4. Middle School Best Boy Friend: The Clash

I don’t usually think of this friendship as a crush, but in retrospect I don’t know what else to call it. He wasn’t in my main group of friends and I wasn’t in his. He didn’t play sports or do student government or care about school and I didn’t skate or do drugs or play video games. Torn between the girl group I wanted to hang out with and the boy group I was supposed to hang out with, this friend provided an alternative outside of gender.

At least once every weekend we’d have a sleepover. I’d show him weird movies, he’d show me weird music, and we’d stay up all night laughing. I loved him so much and cherished our time together. It was an escape from the everyday middle school anxieties. He exposed me to a lot of music, but I most remember The Clash. He taught me, they taught me, that sometimes you have to break the rules and tell society to fuck off. But I wasn’t ready for this message yet. And we eventually drifted apart.

5. Alison: The Edukators

I met Alison in a summer class before high school. They’re two years older and I mostly just watched them from afar. It felt like fate when we ended up in the same yearlong drama class. The first six months of school I was recovering from a serious injury and I’d lost most of my friends. I was depressed and barely making it through each day. Crushes were a life raft, not something to act on.

But in the spring we both signed up to be in The Wizard of Oz. And one day Alison brought a portable DVD player to rehearsal to watch this movie called The Edukators during some downtime. They wanted to know if anyone wanted to join. Most scoffed at the idea of a foreign film, but all I did at this point in my life was watch foreign films, so I was thrilled. I would’ve said yes to any activity, but this just showed we had similar interests and were meant to be. The two of us sat in the back of the auditorium and watched this German movie about three activists who harass and torment the bourgeoisie. Watching the film through Alison’s eyes, it felt like a call to action. Like with my middle school friend, I felt drawn to radical change, drawn to difference, drawn to them.

Alison and I became closer and closer and closer until finally I told them, a year post-Edukators, that I had a crush on them. I was 16 and I was so young. We kissed and I felt for a brief moment like my life made sense. I thought this kiss meant we were a couple. It didn’t. It meant we kissed. I felt betrayed. I felt hurt. I ruined our friendship. I was so young.

We reconnected years later. I apologized for how I’d acted. They graciously accepted my apology. And then they came out as non-binary. Again I watched from afar. When I was finally ready to face my own transness I sent them a message. They were the third person I came out to. I’m forever grateful that I had their friendship in high school, that I knew I wasn’t alone, even if I didn’t know why. And I’m forever grateful that I had their friendship when I was coming out. I’m forever grateful that I have their friendship now.

6. Class Crush: Daisies

We were in the same art history seminar my first semester of college. I glanced at her name on the attendance sheet and looked her up later on Facebook. Like me, her cover photos were always movie stills. City Lights, Taxi Driver, and something I didn’t recognize: Věra Chytilová’s Daisies. I watched it on YouTube and it blew my fucking mind.

Daisies is about two women, both named Marie, who gorge on food, harass men, and generally create feminist havoc. Determined to end the endless crushes of adolescence, I quickly asked my classmate on a date. She treated me with a similar havoc as the Maries. Mid-date she invited me to a party where she went off and slept with the host. I stayed, in slight disbelief, even as her friends confirmed what was happening. She returned post-sex and our date continued. We left the party and chatted at a diner.

For a long time, I saw this date as proof of my low self-esteem. But now I think I stayed out of amazement. I wanted to be part of this misandry. I wanted her brazen confidence. I wanted to create feminist havoc.

The first picture I posted on the internet post-transition was from Halloween. My girlfriend and I dressed as the Maries. I captioned my new profile picture, my first profile picture, with a line from the film: “We are young and life is long.”

7. First Girlfriend: How to Survive a Plague

I met my first girlfriend in a social activism scholarship seminar. She was a year older and was already interning at Red Hot, a non-profit with the motto “Fighting AIDS through pop culture.” She announced one of the first weeks that Red Hot was hosting an early screening of the Act Up documentary How to Survive a Plague at IFC Center and she was organizing a group to go. I seized my opportunity to hang out with her outside of class and went to the screening. She wasn’t there. Something else came up.

But I saw the movie and was moved and inspired. Afterwards the group of five older queer people from my seminar asked me to grab a drink at Brad’s, the NYU bar that didn’t card. Even though I got my scholarship due to queer activism, I felt guilty being with them as a supposed cis straight man. I also felt guilty and confused by the immense feeling of belonging they gave me. That taste of community was all I’d get until years later when I came out.

My first girlfriend and I eventually did hang out and dated and hit several straight milestones together. We were each other’s first serious relationship, we lost our virginities to each other, we met (some of) each other’s families, we even lived together for a summer.

She came out as queer soon after I came out as trans.

8. Cinephile: Goodbye First Love

My first girlfriend and I were long distance for six months before we broke up. We barely talked the last three. During that time, I developed a guilty crush on one of my classmates. She was everything I thought I wanted coming to film school. She was an aloof cinephile with a cute accent who almost exclusively wanted to talk about theory. She recommended a lot of movies, including Mia Hansen-Løve’s Goodbye First Love.

This movie about a young woman who falls in love, then attempts long distance, then falls into the arms of another, was too much for me to bear. I stopped flirting with my classmate, instead seeking out Hansen-Løve’s previous film about a middle aged man struggling with depression. The next year I’d see her new film, Eden, at the New York Film Festival, and, single, go on a date with my former classmate. The movie was great but the date was just fine. I love movies, but for the first time in my life, I didn’t want to be defined by them. I discovered there was more to me than what I’d seen. There was more to romance than theory.

9. Cool Girl: Bill Viola

We met studying abroad in Paris and I immediately had a crush. There were times it felt like she liked me, times it felt like she didn’t. She was so cool. She smoked a lot of weed and knew the best art and was just the right amount of intimidating. I developed a fantasy where I became a stoner and we smoked together and talked about art just the two of us. This never happened. But she did tell me about this video artist Bill Viola who had a show at the Grand Palais. She described him as a god and I went the following weekend. The work was interesting. I stood and watched these abstract experiences for hours trying to find God.

Nothing happened while we were in Paris, but we’d go on several dates over the next six months. I never knew if they were friend dates or date dates and she’d always ghost for awhile in between before texting me again. The following year I returned to Europe. I went with a friend to Amsterdam and spent three days completely high. We went to see a Bill Viola exhibition at 11am deeply stoned. And it happened. I found God.

I’d become my own stoner girlfriend.

10. My Soulmate: Beyoncé

One of my best friends told me she met my soulmate. I was thrilled. This is, of course, what I’d been looking for. But I was studying abroad, then she was studying abroad, so we wouldn’t meet until a year later.

We tried. We really did. We went on several dates. And she was great! And I’m great! But we were not great together. We ultimately decided to just be friends. But early in our failed courtship we were in the car together when “Flawless” came on. I said that I didn’t really get Beyoncé, that she wasn’t really for me. My soulmate flashed me such a look.

There are reasons Beyoncé is not specifically for me. But in this moment I wasn’t talking about race. I was talking about gender. I didn’t listen to any pop music because I so deeply associated it with women and gay men. And I was still trying so hard to be a straight man. But this supposed soulmate of mine was so dismissive. How could anyone deprive themselves of Beyoncé? She was right. I immediately felt like the biggest idiot in the world. Beyoncé opened an entire genre and soon I almost exclusively listened to pop music.

By the time Lemonade came out I had a Tidal subscription.

11. Pace Freshman: Devendra Banhart

We met at a concert on Valentine’s Day. I was drunk and asked if I could give her my number and she said yes. On our first date I learned that she was a freshman at Pace. She was sweet, but she did feel young. I didn’t feel any sparks. But I was trying to be less picky and sangria is helpful. We kissed and it was fun and then we dated for a bit. She made me a mix CD, one of my very favorite things to receive from anyone, but especially from someone I’ve just started to date. I tried to like it. I really did. It had a lot of Devendra Banhart on it.

It’s hard to go back to indie folk after you’ve discovered Beyoncé. In so many ways it felt like my attempt at different patterns was just leading me back in time. A month later, I sobbed as I broke up with her. I sobbed because I felt guilty. I sobbed because I worried I’d always be alone. I sobbed because I still couldn’t find a woman to fix my gender-confused brain.

12. Friend with Benefits: The Bell Jar

One of my other Paris crushes became a close friend. She lived in LA and when we saw each other we’d flirt and almost hook up. Until, eventually, we did. We would continue hooking up, in person, via FaceTime, for about six months. During this time I was deeply depressed but our moments together cheered me up. Until they didn’t. She’s the only cis straight woman I’ve ever actually been with and it felt like I was playing a role. It was fun to experiment, it was fun to be with someone safe, but I was becoming increasingly aware that my attempts at being a straight man were waning.

Her favorite book was The Bell Jar and I read it during our longest time apart. I related so deeply to its female depression. It felt good to wallow, but I found myself slipping further and further. I knew how this ended for Plath and I knew how it would end for me. I finally went back to therapy.

13. Katharine: All I Wanna Do

When Katharine and I first met she hadn’t seen any movies. This is, of course, not true, but it’s what she said. What she meant was she hadn’t seen The Godfather, Citizen Kane, or any of the other classics of masculinity. Instead she spent her adolescence watching Feminist Teen Movies. We quickly realized I had more interest in watching those than Katharine did in catching up on the canon.

We started with All I Wanna Do, Sarah Kernochan’s deeply underrated boarding school classic starring Gaby Hoffman and Kirsten Dunst. Then we moved on to But I’m a Cheerleader. The rest was history.

And by history, I mean Katharine turned out to be the person I’d always been looking for. Crush after crush, relationship after attempted relationship, I finally found the woman who completed me. Except I didn’t. Because that’s not a thing. I had to face the truth: no woman I dated would solve my gender problems. After a year and a half of dating and a year and half of watching these movies, I began my own teen girl coming of age story.

Using these movies as markers, I fumbled through women’s fashion, putting on makeup, developing breasts, shopping for a bra, and crying at just about everything. All the milestones except my first period.

Katharine was with me the whole time and so was All I Wanna Do, and But I’m a Cheerleader, and Bring It On, and Welcome to the Dollhouse, and Real Women Have Curves, and Hairspray, and Psycho Beach Party, and Miao Miao, and Valley Girl, and Jawbreaker and Princess Cyd and Raw and rewatches of Clueless, so many rewatches of Clueless, and Lady Bird, so many rewatches of Lady Bird.

When Katharine and I broke up it must’ve been a relief to never again hear the question, “Wanna watch Lady Bird?”

14. Rebound: Hannah Diamond

We had sex the week Katharine and I broke up. It was really nice. It gave me confidence as friends and family asked without asking (or sometimes just asked) if I’d ever find someone again. Being a trans woman and all.

She was a musician and recommended I listen to Hannah Diamond. It became my soundtrack for several months. I still listen to her a lot. She’s fun and sexy and a little sad. The perfect tone for my new single life.

We’d have sex one more time before she ghosted. Or whatever it’s called when someone doesn’t respond to your texts but likes all your Instagram posts.

15. First Crush: Lost & Delirious

I ran into my first crush at a concert. We had a magical night dancing and talking and flirting.

On the Lyft home she sent me two texts. The second read: “Let me know when you make it home!” The first just read: “Lost and delirious.”

She’d recommended it to me and didn’t want me to forget. It was the lesbian movie that defined her adolescence. I knew what to do. A few days later I rented it.

I watched the movie so I could text this person, but that quickly became besides the point. Because teen angst! Because Piper Perabo! Because falcons! My love for teen movies, especially gay teen movies, is obvious, and this one in all its silliness so deeply captures the immense emotions that arise in adolescence. First adolescence and second adolescence.

I texted my crush and said that Piper Perabo was my dream girl and she responded that Piper Perabo is who she’s always modeled herself after. I went to sleep feeling excited and horny and uncertain. The usual crush feelings. It was the first time I’d really felt that way since being single and it confirmed why I’d made that choice. Deciding to be single to fully embrace your crushes isn’t silly. Because crushes are never just about the crush.

We continued flirting on and off but it slowly fizzled out. It didn’t matter. It was never about the crush. It was about having a crush at all.

It was about Lost and Delirious.

Drew is an LA-based writer, filmmaker, and theatremaker. She is currently working on a short film about Gordo from Lizzie McGuire’s transition (it’s canon) and a million other projects. She also runs social media for I Heart Female Directors. Find her on Twitter and Instagram @draw_gregory.

Drew has written 44 articles for us.

10 Comments

  1. Drew this is so spot on: “I love movies, but for the first time in my life, I didn’t want to be defined by them. I discovered there was more to me than what I’d seen. There was more to romance than theory.“

    I had a similar realization that drove me from theater/film in undergrad into a women’s and gender studies master’s program (and forced me to meet my burgeoning queerness head on)💜

  2. Oh, wow this is too real. My first/best example is probably my devastating crush on a girl I was friends with from middle school through the few years we were at community college together. She was 50% Irish, 50% Puerto Rican, 100% saving herself for marriage, and very proud of all those things. She played me The Dresden Dolls’ ‘Coin Operated Boy while we sat in a cornfield, and they are still unironically my favorite band today.

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