When my sister was in sixth grade and I was in third, I walked into her room without knocking.
She was naked, jumping up and down — a goofy child fascinated by her new chest. She shrieked a death scream to match her stab of embarrassment. She told me she hated me. She complained to my mom. And I started knocking whenever I dared to enter her room.
As a kid, I latched onto my sister and her friends. I took whatever role I could get in their games of make believe, happily obliged any rules as long as I could play. The eagerness of a younger sibling and my hidden transness combined to create a child desperate for these older girls’ approval.
But middle school changes a person — especially a girl. My desire to be close with my sister was replaced with a desire for her and my mom to just stop screaming at each other. My yearning for approval was replaced with a confused dread as she vented about older boys.
I witnessed her middle school years with a mix of horror and envy. My birth announcement may have read: “Boy, oh boy! Liz and Keith Gregory are proud to announce the birth of their son.” But it wasn’t until my sister went through puberty that I truly realized I was a boy. There was a new distance between us — one I couldn’t expect to disappear.
When it was my turn to go to middle school, I wouldn’t understand her more. Supposedly, I would understand the boys she crushed on, complained about, ignored. My body would change in different ways.
Make believe was over.
Pen15 came out two years after me.
Co-created by Maya Erskine and Anna Konkle along with frequent director Sam Svibleman, the show stars Erskine and Konkle as versions of their middle school selves. This allows them to explore the often too adult experiences faced by young teens — specifically girls in the year 2000 — without exploiting actors of that age. It also further alienates the two leads since all the other middle schoolers are played by actual middle schoolers.
The show is brilliant in its specificities — of the era and of middle school in general. Sure, things like AIM and taking out your retainer before a first kiss, but also the ways certain girls would tie up their PE uniforms to look “sexy” or the cadence in a girl’s voice as she plays messenger to her best friend’s crush.
Watching the first season during what I considered my second puberty was miserable. I could acknowledge its effectiveness, but I felt alienated. I was reminded that middle school wasn’t just the beginning of boy-girl parties but the painful reality that those parties ended with the girls having one sleepover and the boys another. Never was I more grouped in with “boys” than middle school. The show didn’t feel relatable — it reminded me of all the beautiful suffering I’d missed.
I pitched an essay about this experience but gave up during my rewatch. It’s the only time I ever missed a deadline. And when the show came back for a two-part final season, I opted not to watch.
It’s been a year since the series finale, and I’ve been out for more than half a decade. The scars of middle school, of transitioning, of 2019, have all faded. And so, I finally watched those last 15 episodes.
They still made me cringe, they still made me ache. But the resentment, the distance, had died with the ease of a Tamagotchi.
The last eight episodes of Pen15 are a departure for the show. Not only do they begin with an animated vacation special and include a bottle episode about Maya’s mom, but their overall focus leaves behind the school setting for darker explorations of alcohol, death, and sexuality.
After the animated special, one episode acts as a bridge. “Bat Mitzvah” follows Anna questioning the existence of God after learning about the Holocaust — and, more importantly, still dealing with her parents’ divorce. Meanwhile, Maya is desperate to prove she isn’t poor by getting spoiled Bat Mitzvah girl Becca a gift Maya’s parents can’t afford — a butterfly necklace from Swarovski, of course.
This provides the half season with one of its only moments spent with Sam, the mostly sweet boy who has been crushing on Maya and was a major part of the first season and a half.
Maya walks up to Becca and her popular friends to give her the necklace. Becca points her to the gift table. When Maya convinces her to open it in front of her, the soundtrack fills with “Let Me Tell You” by Smooth Approach. The way a music cue on the show can indicate a crush is used in this moment of desired straight girl approval.
“Want to dance, Maya?”
It’s interrupted by Sam. First-kissed-obsessed Maya, obviously-crushing-on-Sam-too Maya laughs Sam off. She says, “No, because you don’t have good shoes,” repeating an insult she heard these girls use earlier.
He walks away, confused and defeated. Becca says she already has a couple of these necklaces and tosses the expensive gift to the side without a second thought.
Maya finds Anna, who has found high school boy Steve. He gives them alcohol and tells Maya he has a friend named Derrick who wants to meet her.
We don’t see it, but somewhere Sam is wondering why Maya doesn’t like him anymore, why Maya was mean to him to impress some girls who aren’t even her friends, why girls care so much about things like shoes.
Or, at least, that’s what I would’ve been thinking.
My own Bar Mitzvah marked a shift in the genders of those around me. I may not have become a man but I watched as my friends started to become their own little men and women.
Before then, I had cherished the friendships allowed by middle school social dynamics. My group of guy friends had a group of girl friends we would eat lunch with and who would attend and invite us to boy-girl parties. Sometimes we’d hang out with them at an outdoor shopping center called The Promenade that had a movie theatre and a Barnes & Noble. We went to the high school football games together, and some of us even dated. I could be around girls, even if I couldn’t always relate to their dramas.
Sometimes I even managed to transcend this divide. One year, I mentioned to my best girl friend and longest held crush, Ali, that it wasn’t fair that the girls decorated each other’s lockers for their birthdays and gave each other tiaras while the boys didn’t. I said it as a joke, but I’m sure my truth betrayed me. A couple months later, Ali and some other girls decorated my locker for my birthday. They even gave me a tiara. I wore it all day. As a joke.
That was sixth grade. By the time I was Bar Mitzvahed in the middle of seventh grade, everyone was trying to be more adult. My friend Tyler was the only exception. He wasn’t in my friend group, opting to hang with a less normie crowd. He danced and played guitar and that night he was the only boy with skills to impress the DJ’s hot employee. (Fun fact: the hot employee would go on to star in Step Up 2: The Streets.) That’s the last time I can remember the rest of my middle school friends admiring a quality outside a strict gender binary.
Since I’d already witnessed my sister go through puberty, I was familiar with the thoughts and experiences of cishet middle school girls. But that didn’t mean I understood it.
I’d watched my sister cry because my parents wouldn’t get her a Juicy jacket. I’d watched her daydream about her first name in front of the last name of some boy she’d had a crush on for a week. I’d watched her go through best friends and frenemies and nemeses, have rumors spread about her, and spread rumors about others. I decided most of this was because she was trying to be in the popular group. I wasn’t prepared when my own friends started acting the same way.
Middle school boys were a different kind of nightmare. Not being fully accepted by the girls could be painful, but moments alone with the guys were a different kind of challenge. As I grappled with my own burgeoning sexuality, I had to bear witness to some horrid attempts at manhood. Some of the guys I knew didn’t date or talk about crushes or talk about sex — this was very much not me. But the guys who were as interested in girls as me expressed that interest differently. They talked like stereotypical straight men, whereas I was a confused little lesbian.
I didn’t want to talk about which girls looked hottest in bathing suits — even if I’d noticed and immediately felt ashamed. I wanted to talk about love! I wanted a boy equivalent of seeing how my first name sounded with a girl’s last name. I wanted my first kiss, not my first handjob.
I slow danced for the first time at my Bar Mitzvah. Despite my Judaism, we left more than enough room for Jesus. This is how I continued to dance with girls, unaware when the rules suddenly changed. At the last school dance of middle school, I asked my crush to slow dance. My friend who had a crush on the same girl got all the other guys to shove us closer and laugh at me for standing so far apart. Afterward, he told me I’d wasted dancing with her since her boobs hadn’t even been pressed against me.
According to an endocrinologist, I was two and a half years behind developmentally. (They offered to put me on testosterone because that’s no big deal when it’s for cis kids.) This meant I was an adorable sixth grader. I had long hair and an easy confidence. By eighth grade, I’d been pressured into chopping off my hair and I got braces for the first time. My awkward phase started when my friends were trying harder than ever to be heterosexual men and women.
My guy friends began convincing younger girls to make out with them. My girl friends started dating high schoolers. There were no more tiaras on my birthday.
By the time Maya is meeting Derrick, at Anna’s grandma’s funeral, she’s already been declared UGIS (ugliest girl in school), been catfished by Sam (I said mostly sweet), and been dumped by her showmance Gabe who wouldn’t even kiss her (he’s gay). Meanwhile, Anna got her first kiss with a former boyfriend and is now always making out with new boyfriend Steve.
Maya is desperate for her first kiss — a relatable feeling as someone who once wrote in my journal, “I’M FOURTEEN AND STILL HAVEN’T KISSED A GIRL.” It’s understandable that her standards aren’t high even if Derrick is more interested in her ADD meds than getting to know her and at one point calls her Lucy Liu.
It also makes sense that Anna has sought out Steve in the first place. They had a fun rapport when working on the play together, and he understands the experience of parents divorcing. She’s isolated at home, angry at her parents, and here’s this older guy who seems to understand the world and her.
Not that seventh graders need excuses for poor choices.
The conclusions of these relationships are inevitable. The alcohol and drugs, the older boys, the youth and immaturity and desperation of Maya and Anna. I spent my childhood hearing about teenage boys from my sister. I spent my adolescence hearing about teenage boys from themselves.
It doesn’t make the scene where Derrick coerces Maya into giving him a blowjob any less painful. It doesn’t make him breaking up with her the next day — before she’s even had her first kiss! — any easier to watch. It doesn’t make it any more disappointing when Steve takes Derrick’s side.
Toward the end of eighth grade, all my friends went to Six Flags.
By this point, we were barely a friend group. But for this kind of thing, we were all there — boys and girls. Ali’s older brother and some of his friends came with us as well. My crush on Ali was over, but my desire to be close with her again was still strong.
Because of my sister, I knew my friends’ new lives weren’t ones to envy. And yet, I couldn’t help but feel jealous when they talked about older boys. They were looking toward high school, where they’d only grow further from me. It seemed like a choice to me, and they were making the wrong one.
At one point in the day, Ali and another friend of ours were talking about something private. Maybe it was a secret story about a boy, maybe it was as simple as asking to borrow a tampon. All I know is it was labeled “girl stuff” and I wasn’t allowed.
I got so upset. I begged her to tell me. I didn’t understand why she couldn’t trust me when we used to be so close. They walked away, and her brother told me I should let it go. He told me that I don’t want to hear about her girl stuff anyway.
But I did. I really, really did.
I hadn’t accepted that their girlhood would never be my girlhood, because I didn’t know I was experiencing a girlhood at all. I didn’t even know the word trans let alone that it described me. I’d heard a rumor that Ciara used to be a man and I’d seen a brief thing on Oprah and that’s it. All I knew to do was beg my friend not to keep “girl secrets” from me.
In a sense, I was still begging when I watched that first season of Pen15.
My first version of this essay from over three years ago ended with me naked, looking at myself in the mirror, jumping up and down. The idea, I suppose, was that my puberty may have been delayed — far more than that endocrinologist thought — but eventually I got to have the same moment of exploration as my cis sister.
In 2019, I was still really attached to the idea of second puberty. Even though I was 25, I allowed myself the grace of youth. I told myself I was making up for all those years that had been stolen from me.
I was wrong.
Not only did that excuse an immaturity in my adulthood, but it did a disservice to the girlhood I did have. It may have taken longer for my body to change in the correct ways, but as a kid I fought hard to have a life worth living. Yes, I found ways to be around girls, yes, for a day I got to wear a tiara, but my greatest triumph wasn’t with other girls. It was with my own Anna, my own Maya, my best friend, Tyler.
There are so many funny and painful moments in Pen15 where the girls grapple with their bodies, their hormones, the intricacies of puberty. But there’s a reason the show ends with the girls having a sleepover, watching home videos of their friendship.
Maya and Anna have just egged Derrick’s house — okay, thrown fish at it — and Maya has finally had her first kiss — with Sam! — and after all this excitement they’re alone, together.
“Do you think that there’s ever a time that we won’t be friends?” Anna asks. “Like what if after college you get a little bit depressed and I’m a little irresponsible and we’re both just so super dependent on each other and I can’t take it anymore and we don’t laugh like we used to.”
“Or the things that we didn’t think would bother us about each other. Or our parents. Or the way we see the world starts to eat at us, and we just get like really cynical. And really we just like wake up one day and we’re not friends,” Maya adds.
Their sadness gives way to a new fantasy: “Or we share a dorm!”
This is a show about how hard it is to be a middle school girl. It’s also a show about how having that one good friend can make it so much better.
While I was navigating the dynamics between the girls and the guys in my friend group, I had an escape every weekend with Tyler. Saturday mornings may have been reserved for soccer games, but Saturday nights I’d go with Tyler to his dad’s house. Tyler would introduce me to weird music — shoutout Nirvana — and I’d introduce him to weird movies — shoutout Escape from LA — and we’d stay up all night in the attic laughing, talking about art, talking about girls but not in a gross way.
Maybe Anna and Maya will share a dorm together. Or maybe this intense friendship, like so many intense friendships of youth, isn’t meant to last into adulthood. Either way, it’s special for them now.
I haven’t talked to Tyler in over a decade. Sometimes I look him up on Instagram and see that he’s still playing guitar. I don’t think he’s still dancing. Maybe one day I’ll reach out to him and we’ll catch up. But I’m just grateful he knew how to love me and I knew how to love him at a time when it’s so easy to feel unlovable.
I missed the point of Pen15 when I started it all those years ago. It’s a show about girlhood, it’s a show about middle school, it’s a show about the year 2000, but most of all it’s a show about friendship. Maya and Anna are at a time in life when the world is telling them all they have to be. And then they have each other — two beautiful weirdos who embrace the entirety of one another.
I should’ve had a different girlhood. That endocrinologist should’ve offered me estrogen instead of testosterone. But with each passing year, I become more comfortable with my own version of girlhood, my version that had Tyler. He was a beautiful weirdo who embraced the entirety of me.
Slow Takes is a series of “belated” reviews by Drew Gregory of queer art released last year that Autostraddle didn’t cover.
Drew, this is LOVELY.
I felt this in my soul. Beautiful essay, Drew.
I love this so much, beautiful
Loved this, Drew.
I always enjoy your writing 💚🎀💜
Loved this piece!