A Personal Essay That People Want To Read

by Emily Gould

Writing Personal Essays That Get Read

An Online Skillshare Class by Emily Gould

Hi! I taught a Skillshare class about personal essay writing and you might recall that Hairpin readers were invited to join the class, and that I promised to pick one of the essays to be featured here “at the end of March,” by which I meant “May.” You can still take the class — and I think you should. It’s fun, you can do it at your own pace, and the feedback students give each other turned out to be so thoughtful and helpful. Here is the winner:

Getting My Shorts Straight by Daniel Lupo

I could tell that this writer had put time and energy into thinking about the rhythm of his essay. He hones in on a lot of small details and moments that combine to create something that’s both funny and serious. The play on “closet,” literal and figurative, could be too-cute if not handled deftly, but I really felt it was, here. Also, this part made me lol:

“Out of the blue, Miss Hannigan asked us, “So are either of you gay?” Daddy Warbucks and I both said we weren’t and asked her what made her think we were. “Well, you’re both in the play and the orchestra,” she replied, apparently forgetting that I was also in the band.”

(Minor tangent: I was also in a high school production of Annie — I mean, weren’t we all? — and I have to admit that I still think of some classmates by the names of their Annie characters, 15+ years on. Also, I just saw a poster on the subway for a history channel miniseries starring our Annie! Shout out to Montgomery Blair H.S.! I was an orphan without a name, if you’re wondering.)

Moving on! The two runners-up:

Tiresias At The Post-Office by Michael C.

Lys Mediteranee by Nadia B.

Both of these essays were favorites with other class members, too. They share a lyrical, impressionistic quality and their authors both have a gift for memorable turns of phrase.

Without more ado: the winning essay!

Getting My Shorts Straight by Daniel Lupo

It was 2002, during the golden age of the baggy cargo short. On the day of the mandatory spring orchestra assembly, there were around a dozen of them draped over the benches of the basement gym changing room, a grand total of at least fifty oversized, superfluous pockets. Having scored an early dismissal note for gym class so I could prepare for the assembly, I burst into the changing room and dressed in a frenzy even though I still had plenty of time, breaking more of a sweat in the process than I ever had on the soccer field. I gathered all my things and bolted upstairs, my clunky violin case thumping against my voluminous shorts.

Midway through the concert, I noticed my gym teacher towering in the doorway behind the rows of stoic faculty and zombified fifth and sixth graders. I was pleased to see him standing there, because even if he was only a casual spectator, maybe at least he could see that I made up for sucking at soccer by excelling at vibrato, that I could actually be good at something in a gym. He never picked on me for my athletic shortcomings, but he never encouraged me either, and I always feared that his tolerance might one day reach its limit. I wanted to show him that I was a completely different person in orchestra clothes than I was in gym clothes, just in case he thought fitting in to the latter was all that mattered.

* * *

The dress code for my middle school orchestra concerts consisted of beige pants or shorts, a white shirt, and a musty, school-provided cotton vest that was a shade of powder blue I’m pretty sure was only manufactured in the 80s. I played the violin for the first two years of middle school, then quit because I thought it would be cooler to play clarinet in the band since they got to wear cobalt blue sweaters, then re-joined when I saw that the orchestra kids had started dangling Christmas ornaments from the scrolls of their instruments. By eighth grade, I had become the coolest: I was in both the orchestra and the band, and nothing made me feel more important than when I would take off my orchestra vest, descend from the gym stage steps, and don my itchy band sweater in the middle of the joint holiday concert. In hindsight, I never really cared about the instruments, just the clothes and adornments that went with them, however dorky they may have been. Changing uniforms in front of an audience made me feel an exclusivity that, unlike most of my middle school years, didn’t carry with it the vague fear of being excluded.

* * *

When the assembly was over, the audience quickly applauded and then fled the gym in one relieved mass. But my gym teacher was still standing in the doorway, and when he caught my eye he beckoned me to come see him. I immediately knew that I had done something wrong, because what else could it mean when your nine-foot-tall, mustachioed gym teacher summons you with his index finger? I cradled my violin in my arms and shuffled past the empty folding chairs toward whatever terrible, sports-related punishment he had in store for me for leaving the soccer game early to play Mozart with limp wrists.

Instead, when I lifted my gaze from the ground, I saw that he was holding up a pair of shorts with a smile that was either empathetic or ironic. “Are these yours?” he asked. I looked down again and realized that the ones I was wearing felt a little big on me and were slightly darker than I remembered. Then it hit me. Those weren’t my Old Navy shorts — they were someone else’s. And not just anyone’s: he told me they belonged to Zac, who was perpetually tan, played every sport in existence, had never spoken a word to me, and looked like a slightly less hot Zac Efron (hence the alias). I had played my last ever middle school orchestra concert in the roomy cargo shorts of a teen-idol-esque jock. The shorts were made not by Old Navy, but — inevitably — Abercrombie & Fitch.

As I righted my wrong back in the changing room, I noted that Zac hadn’t continued the blunder and accidentally put on my shorts thinking they were his. He apparently knew his shorts better than I knew mine. I assumed he was disgusted that I had been wearing his the whole time, and I was surprised that I wasn’t disgusted at all. Growing up, I never thought that girls had cooties, but that boys did and that I was the exception. I didn’t know what to make of the fact that I secretly liked being exposed to Zac’s cooties and the simultaneous apprehension that I might never have been entirely clean to begin with, that I might have had cooties of a different kind.

When I arrived late to my language arts class, Zac was still in his gym shorts, slouching with his arms crossed and his legs spread wide. I handed him the contraband, which I had neatly folded, and whispered that I was sorry, barely disrupting the class aside from a few confused stares from my classmates. He took them with a brusque smile, I sat down and pushed my chair in until my bellybutton touched my desk, and we continued never speaking to each other.

* * *

About a month or so before the assembly, someone asked me if I was gay for the first time. I was sitting on the gym floor with two sort-of friends during a rehearsal for Annie. They both had lead roles, Miss Hannigan and Daddy Warbucks, whereas I had a bit part as Franklin D. Roosevelt, who only has four deus-ex-machina lines at the end of the play. Out of the blue, Miss Hannigan asked us, “So are either of you gay?” Daddy Warbucks and I both said we weren’t and asked her what made her think we were. “Well, you’re both in the play and the orchestra,” she replied, apparently forgetting that I was also in the band.

I didn’t deny anything about myself because of her comment, but I didn’t admit anything to myself either. I did, however, consider trying out for track shortly after, but the coach said I couldn’t do it if I was already in the play because of “scheduling conflicts.” Though I was relieved, I insisted that I could probably get out of having to attend every rehearsal since I was only in one scene. He still refused. I was still relieved.

My teenage closet was organized around a similar habit of ad hoc self-reinvention — the constant attempts to change in and out of a few different roles, costumes, and uniforms; the barely conscious anxiety that it might mean something if they conflicted with one another or just didn’t fit.

* * *

When looking back on your closet, it can be cathartic to identify the various people and events that caused it to be constructed. But sometimes you can’t attribute everything to jocks and gym teachers and young Miss Hannigans. Sometimes it’s hard to know why your shoulders are still dusted with debris from your demolished closet that never seems to come off.

In high school, my straight drag evolved from cargo shorts and polo shirts to jeans and Ramones T-shirts that I wished were Blondie T-shirts. By my second semester of college, the straight drag had mostly disappeared: I grew my hair long and wore a lot of purples and pinks, but I never once wore a pair of shorts. I’ve maintained an aversion to shorts for most of my twenties and have only recently reintroduced them into my closet, as it were. It’s tempting to believe that the Great Orchestra Snafu of 2002 was some traumatizing milestone that prevented me from ever wearing shorts again until recently, but that might be too much of a stretch. Imposing a narrative on your closet can also be cathartic, especially if you didn’t realize you were ever in it to begin with until you were out of it. At the very least, I can say that ever since that day, shorts have always seemed to signify certain things about myself I don’t totally understand, and their general absence in my wardrobe was a distinctive feature of my closet. Nowadays, whenever I wear them, they still feel like someone else’s. Only this time they belong to another gay guy, who’s been wearing the same tailored, knee-length style all his life, who never had very much at stake in getting changed.

Previously: The Best Time I Wrote A Personal Essay People Wanted To Read