The Gayest Things I Did in My Twenties

I’m 20, and I live two lives: one on Tumblr and one in an ugly brown house in Ann Arbor that I’ll revisit over and over in future dreams. Sometimes those lives touch, but most of the time, I am desperate to keep them separate, to leave myself cleaved.

I’m 27, and my girlfriend has only seen snow a few times in her life, and we’re driving cross-country, a little dog in the backseat and the trunk full of everything we think we need for five months of life together. She says I’ve never seen rain fall sideways like this before, and I say that’s not rain, and I describe what a “wintry mix” is, and I ask if we should pull over, if we should switch drivers, because I’ve driven in snow in Michigan, in Virginia, in Vermont, in Colorado. But she says no, she’ll be alright. And she is. She drives us just fine, slows down, takes care.

I’m 21, and I have a crush on my friend, but I don’t yet have the language to call it a crush even though I do know what a crush looks and feels like, but it’s different if it’s a girl — then it’s just an intense friendship, right? Our friendship is, indeed, intense. Codependent probably (definitely). I’m deeply closeted, so I’m operating on closet logic, which is not so logical at all, and closet logic tells me to pivot and project the crush onto her best guy friend. So I sleep with him and go to a James Blake concert with him and, weirdly, buy him a satchel of cool rocks for his birthday even though we are not dating and he has not told me he wants a satchel of cool rocks and if anything what I really want is for someone to buy me a satchel of cool rocks. It implodes the friendship between me and the girl I’m really crushing on, and we’re both confused about a lot of things, and one of our coworkers keeps asking if we’re secretly dating, if we’re secretly breaking up every time we argue at a party, something we do kinda a lot. She’ll come back into my life at the exact right time and the exact right place, but she’ll also want to rehash the past, and I only really do that in essays.

I’m 25, and I’ve just adopted a little calico kitten with my girlfriend, who won’t be my girlfriend much longer, who is also the girl who couldn’t remember Rachel Bilson’s name, but you haven’t met her or heard that story yet. You will soon; I just haven’t decided where she belongs. We got the kitten from a shelter in the suburbs of New Jersey, and she’s tiny and stinky. And when I carry her around in my shirt like a mama kangaroo, I don’t know that she’ll only be in my life for a year or so, don’t know how this tiny stinky perfect cat is going to become a main character in couples counseling one day.

I’m 23, and I tell a girl on Tinder I love the movie But I’m A Cheerleader even though I’ve never seen it.

I’m 29, and I’m writing this essay outside on my balcony in Miami. The bay below glitters in the sunlight. I’m labyrinthing the last decade of my life on the page, because this wild approach to structure is the only thing that makes sense to me as I look back. My twenties were indeed wild in all the cliche ways of drunk nights and bad choices and mediocre sex and shoes that gave me blisters. But they were also wild in the sense that wow I really didn’t know what I was doing or who I was for a while there, huh, and wow I’ve been at least four different people over the spanse of ten years like, jesus, remember when I was telling people I was a TOP? ME? A TOP? Who was she? Who am I? What will I become?

I’m 26, and I put on makeup and real clothes for the first time in many days. I put on a blazer and a dark green cropped tank and black jeans. I look good, so I take at least seven selfies in my living room, which is where I’ve spent most of my time lately, because I hate leaving my apartment, but I also hate my bed. Everywhere feels cursed to the point where I think I’m cursed. But not today! Today, we break the curse, even if it’s only for a few hours. Today, I’m going out. Not on a date-date but on a friend-date with someone I’ve known since before my twenties, someone I originally met online (which is something I can say about more than 75% of my closest friends). We’re going to get a seafood tower, and it’s my friend’s first time, and this is something I love, have always loved, will always love: watching someone taste something for the first time.

I’m 24, and I’ve just finished writing the second season of the gay ass webseries I made with two friends, who used to be girlfriends but aren’t girlfriends anymore even though they still live together and co-parent multiple cats, and sometimes I feel like their weird daughter even though I’m the same age as them. The second season is much better than the first season; I can feel it. I’ve watched my writing strengthen, tighten, but also expand. The second season will never get made, and I will eventually look back on the first and think wow that wasn’t very good at all, but right now, something’s happening. I’m figuring out the stories I want to tell. And failing at it, too, but that’s important to do sometimes, one of those stupid little life lessons I’ll learn.

I’m 28, and my girlfriend and I move from the desert of Las Vegas to the swampland of Florida, and I’m having trouble getting used to the thunderstorms, which I’ve always hated. And when a crack of thunder rattles the whole house, she’s gentle with me, wraps me in a blue and white fuzzy blanket, pops the dog up, asks me my favorite question: What should we have for dinner?

I’m 22, and I’m about to hook up with a girl in her bedroom in West Hollywood, and she smells like dryer sheets and cigarettes, and her tiny dog is finally asleep on the floor, and my straight guy friend Gus is asleep on the other side of the door in the living room because he’s staying with me in LA and we went out with this girl who I met because she’s friends with his friend and he whisper-told me it’s fine if we go back to her place, I’ll be fine, I’ll just sleep on the couch, who cares and that, my friends, is a Good Ally.

I’m 25, and I go to A-Camp for my first time, and I play beer pong in a yurt with a bunch of queers, and my pong partner is one of the funniest people I’ve ever met in my life.

Oh, sorry, were you expecting a listicle? I wrote a lot of those in my twenties. I filed a lot of 1099s. I never bought a car. I lived in too many apartments to count, in nine different cities. I was in multiple long distance relationships. I made friends online and then met them IRL and learned what their laughs sound like. I swam in the Atlantic Ocean, in the Pacific Ocean, in the Indian Ocean, in the Aegean Sea, in a fjord in Norway so deep the water looked icy black, and when I jumped into it off the side of a concrete pier where people sunbathed and licked at ice cream, I couldn’t stop thinking about what creatures might haunt it.

I’m 23, and I’m not sure if I’m on a date (I’m not). But I am eating hot dogs in a backyard with someone who is about to become a very good friend, who I’ll eat so many hot dogs with.

I’m 27, and I live in the desert with someone I love more than I knew was possible and who makes me a kind of happy I’m not yet used to, so I keep having these embarrassing and overwhelmingly genuine internal moments where I’m like wow can you believe how happy you are right now wtf. I’m making her soup. We’ve known each other less than a year, but doesn’t love always stretch time like hand-pulled noodles? I’ve lost track of how many times I’ve made her soup, cannot know how many more times I will make her soup, but I hope it’s so, so, so many times. Neverending soup, just like at the Olive Garden, where we’ve gone together a few times but not lately, because it’s May 2020. Our life has shrunk down, and our loft apartment in the desert feels like a dollhouse. But we have each other, and we have soup, and it is enough, and even as our lives shrink down, my happiness swells and stretches.

I’m 25, and it’s my birthday, and I do oyster shooters for the first time at a restaurant in Portland, Maine, and the brine of the oyster mixed with the bite of the tequila is a perfect elixir. Later, I have sex in a car and it’s, literally, anticlimactic.

I’m 22, and I only last a few months in Los Angeles before leaving and moving to Chicago, where two friends who are dating say I can live with them, in their living room on their futon, while I get my bearings and start my freelance writing career. I stay for over six months, and their generosity and that clunky beige futon will be the main reasons I’m able to make writing my living for the entirety of my twenties. At night, I cook them vegetarian dinners, and we watch Gilmore Girls, and I’ll owe them for all of this for all of my life.

I’m 23, and my friend Mike and his boyfriend, also named Mike, set me up on a blind date with a girl who works with the Mike who isn’t my Mike but who is dating my Mike. My Mike and I had a brief fling before either of us knew we were gay during our freshman year of college, but that was when I was still a teen, so I shouldn’t be telling you about it, because this essay is very specifically about my twenties, which ended today, May 30, 2022 but whoops I’m really losing a grip on the tense here, so let’s rewind to now, and by now, I mean when I’m 23 and on a blind date. We get drunk, and she can’t remember Rachel Bilson’s name, and neither can I, and it’s making us laugh a lot on her fire escape at four in the morning. I have an early flight back to Chicago, but I won’t be hungover in the morning, because I’m 23.

I’m 29, and I’m writing this essay outside on my balcony in Miami. I decide this is all I want to write about the girl who couldn’t remember Rachel Bilson’s name. She was only three years of my twisting, turning twenties, and even though so much happened, even though the lesbian cliches maintain that I should always be talking about an ex, writing about an ex, it gets so boring lol. Like, that’s enough of that.

I’m 21, and I announce I’M GAY to an audience of friends. A literal audience. I’m on a stage. Or, well, a “stage.” Really, I’m just in the dark and dirty basement of the ugly brown house I’ve lived in for two years. We’re hosting a DIY standup show, and I’m doing a set, and I’ve written this in. My coming out is literally scripted. Some of my friends sprawled on the floor know already. Most of them don’t. It’s a confusing way and time to come out. We’re graduating in a few weeks and also, oh yeah, I have a boyfriend, and he’s in the audience. I do not come out as bisexual or queer or anything that really acknowledges his presence or general existence in this standup set. I say I’M GAY. We don’t break up. He congratulates me after the show, and we both get drunk, and I can tell he has something he wants to say, and we should probably talk about it, truly, but we don’t. Instead, we draw out our doomed relationship and lengthy breakup as long long long as possible, because we both like suffering I guess? When I’m 23 and am hired as a team writer for the website, the first personal essay I write is about my decision to come out as part of a standup set, but my ex-boyfriend does not appear in it. I write him out. Because he doesn’t fit in with the narrative I’m trying to tell or, at least, I don’t think he does. Really, though, he might be the most interesting thing about the memory. The essay’s not a lie. But it isn’t the full picture, is it? It’s easy to cut and paste a scrapbook of the self. Don’t you see me doing it now?

I’m 23, and I do poppers for the first time with a girl who wears a gold nameplate necklace, and when I go back to her place, she has a pet ferret, and when I go back to her place a second night, she has two ferrets. I do not go back to her place a third time, so I am not sure if the pattern continues.

I’m 26, just a little over a month shy of turning 27, and I’m living the series of scenes I will soon like to write over and over and over, always remembering a new detail, forgetting others. I’m on a train on a bridge on my way to meet a stranger from the internet, a little buzzed from a shot of fernet, my hair recently dyed blue during a spur-of-the-moment decision. I’m not usually like this. This person who wakes up and decides to dye her hair blue that very day, this person on her way to meet a stranger from the internet with the very explicit goal of hooking up. I’m turned on by own out-of-character actions. My life is about to change, but I don’t know that yet, because you can never know a thing like that as it’s happening. But I do feel something, these little changes, these little pops of spontaneity, they’re culminating, charging each other. Or maybe it’s just easy to write that back onto the experience in the future. But even my friends say they can see and sense something different about me, and I text them one last text as I go over the bridge to meet this stranger from the internet, and then they don’t hear from me for at least 48 hours because this stranger from the internet, who I’ll live with in a desert, live with in a swamp, live with in a place with a balcony that overlooks a bay that glitters in the sunlight, becomes, all at once, not a stranger, and she has my full attention. When I walk into the low-lit, too loud bar in the lobby of the hotel, I see her there, all the way in the back, perched on a stool with her bag on another, saving it for me. She turns.

I’m 29, and I’m writing this essay outside on my balcony in Miami. When I sit down, I want to write only the good parts. Not a greatest hits album. Not all happy parts either. Just the parts that, when I remember them, I think to myself wow that was so me, whatever that means, because I’m obviously still trying to figure that out. There’s so much I can’t fit here. I’m worried this essay doesn’t have enough of A Point, because it seems like just a cobbled together collage of chaos, but I would be thrilled if someone called me that, a cobbled together collage of chaos like put it on my grave!!!!! It wouldn’t be an essay about aging without a little taste of death now, would it?

I’m 20, and I’ve never said nor written the words I’m gay before, and I don’t know that writing the words I’m gay will essentially become my literal job but also the overarching theme of my creative work and that two words can be like a train going over a bridge, full of possibility and change, their own form of time travel.

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 847 articles for us.


  1. This was fantastic. Had my own late-20s birthday a couple weeks ago and have been weirdly filled with time-based dread – maybe I should be looking forward instead. :) Happy Birthday!

  2. You really have lived life in your twenties. I’m always so impressed with your writings and wanting to read more. I wish the second season of the web series got made.

    I have followed you on social media for a long time it seems, I didn’t realize how long. I’m always eager to see what you are up to next. I can’t wait to see what you write and do in your thirties.

    Happy Birthday Kayla!

    • This essay is fantastic! (Thanks to Slate for linking to it). I’m very old now but remember my 20s much more vividly than any other decade. This brought back even more memories.

  3. I am out here to testify of your great work, my husband is back to me with the kids and leave the other woman at his working place, with your spell and he is in love with me now as you said, and he said there is no need for divorce and he apologized for all the pains he cost me and my kids thanks to priest Adu, if want to know more about work here the contact { } priest@solutiontemple. info your spell work fast and I am so happy to share your testimony…..

  4. I love the “cobbled together collage of chaos” of this piece, Kayla, because it captures life and memory and the stories we tell ourselves about ourselves so well. Thanks for sharing pieces of your story with us!

    A part of me always resist the narratives of “x will be better” (might go back to being a newly-realized-queer 6th grader in a conservative rural area and my teacher telling us that high school would be “the best years of our lives” and even at 12 I thought no, that CANNOT be true), but as someone on the other side of 30, there can be a certainly kind of comfort in one’s self, and even if/though the collage of chaos doesn’t resolve, maybe you kind of realize that’s how this thing works? And everyone feels that way to some degree?

    In any case – Happy, happy birthday! Thanks for sharing your writing (and the role your editing plays in sharping the work on AS) with all of us.

  5. “I’m not usually like this. This person who wakes up and decides to dye her hair blue that very day, this person on her way to meet a stranger from the internet with the very explicit goal of hooking up. I’m turned on by own out-of-character actions. My life is about to change, but I don’t know that yet, because you can never know a thing like that as it’s happening. But I do feel something, these little changes, these little pops of spontaneity, they’re culminating, charging each other. Or maybe it’s just easy to write that back onto the experience in the future.”

    Love this so much and this essay really resonates. Thanks for sharing!

  6. So many beautiful fragments here – like a time capsule – which I would happily read as a whole chapter each

    But sometimes the one liner is perfect as it is – now I can’t stop thinking about about the ferrets!!

  7. I want to use this opportunity to thank and show my appreciation to priest ADU for bringing back my husband who left me and the kids for his mistress for nine months. within the period of 78hours priest ADU was able to bring him back to his family.. I am very much grateful for restoring peace back in my marital home I pray God almighty give you the strength and wisdom to help more people. For help you can reach him on his address: (

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