Oh Gay Cupid! Turning Dating Fails Into Life Wins

Welcome to Oh Gay Cupid! Autostraddle’s OkCupid series. We get lots of questions on Formspring regarding online dating, so we finally got a bunch of people together to talk about it. While OkCupid isn’t the only online dating site for queers, and maybe isn’t even the best, it does seem to be the one we use most often. We’ll be discussing all things OkC, including meeting friends, first dates, profiles, fuck-ups, letdowns and more. Even though it’s the ‘OkCupid Series,’ the advice given in this series could easily be applied to any online dating site.

 Oh Gay Cupid! illustrations by Rory Midhani

Sometimes having an OkCupid profile isn’t about dating, networking, or making friends. Sometimes you think it is, but then it winds up being not. I’m here to tell you why there is no failure on OkCupid, only different angles of success. And I have had some pretty bald-faced OkC fails. Let’s pull out the trusty Oh Gay Cupid board game and see what the dating cards have it store for us this time!


Sometimes Dates Can Teach You About Your Own Self-Worth

I met her on OkC, went on dates with her for hot two weeks and of course I slept with her on the first night. I wasn’t over my previous heartbreak, so it was a good thing to have some nice, consensual touching, kissing and fucking. I think our expectations of each other may have been different. I wanted a no-strings-attached-sex-buddy-but-still-friends relationship, and she wanted…well, I’m not sure exactly. Maybe she just wanted a vagina to put things in? It seemed she was in a similar place about the heartbreak, but she wasn’t nice about it. There was definitely name calling. And there was definitely inviting me places where I wasn’t really welcome and then making me feel bad about coming. And there were definitely definitely several moments where my presentation was called into question:  she said I didn’t look gay enough, didn’t act gay enough and that I had too many straight friends. I mean, WTF?  I ate your pussy, honey. I’m pretty sure that’s gay with a side of rainbows. On the train home I couldn’t take it anymore. I got out four stops early and went to my ex-boyfriend’s current girlfriend’s house to meet up with both of them. Yes. YOU READ THAT RIGHT. They got me wasted and disparaged the human race with me.  And while I was crying over how shitty people can be and heaving my guts into the toilet bowl because I’d had maybe three too many, I remember telling him, “This isn’t worth it. No one is worth this. I shouldn’t let other people make me feel like this.” And being the perfect man (if I were straight, I would have married him), he has never let me forget it.


Even Shitty Relationships Can Get You Jobs and Roommates

So, I was in that shitty relationship. Everyone knows about that shitty relationship because I feel like maybe everyone has had one of these? Or if not, at least witnessed the downfall of one. I went all in and U-Hauled and I couldn’t even finish out my lease with the girl. Right about the time when my ex-girlfriend threw a garbage bag full of my own clothes at me when I came back to collect them, I was pretty down in the dumps on this OkCupid adventure. I swore never to internet date again because clearly this did not work even a little.

But then I reflected and I came up with the following list of things that I never would have had if I hadn’t dated this girl.

+ I left my hometown. I got the hell out. I didn’t even see a gay adult growing up, so you can imagine how imperative this was.

+ She referred me for my day job, and thus my health insurance. And, you know, my paycheck.

+ My cat. She insisted I adopt the cat to keep her dog company when he was going insane by himself in our apartment, and then couldn’t really remember suggesting that. However I got the cat, he is the best.

+ She inadvertently introduced me to higher standards. As in, here, here are all the things you don’t want in a relationship. Don’t do that again.

+ She introduced to me to my former roommates, whom I love very much.

+ I’m a sex blogger. Seriously. This person convinced me that I should just go be a sex blogger, just because I’ve always wanted to. I’ve since been published as an erotica author. It’s been tremendous fun.


Dates Can Tell You About Awesome Things You Should Be Doing In Your Life

I went on one date with her and I haven’t spoken to her since, haven’t even laid eyes on her. I was still living with my ex-girlfriend at the time and we were on the rocks, but I wanted someone to talk to. I wanted something new and interesting, so we agreed to go on this date. She was a circus performer, a stilt-walker. Ever seen a stilt-walker? That’s something that scares the shit out of me. I don’t even like being tall, that’s how much I like heights. And danger isn’t really something that I’d put on my top ten list of things I want to do on a daily basis. But I was intrigued. I told her I’d always wanted to get more into the circus thing, but had zero acrobatic skills because when I was growing up my sister convinced me that if I took gymnastics, it automatically meant I would break my thumb (and my sister has this weird double jointed thumb, so then she’d do this thing with her thumb and I’d get grossed out and I didn’t take gymnastics). So I enrolled in ballet instead and managed to knock down the entire class of girls on parents night, and then my mother burst out laughing and was shunned by the other parents. After that, we made the switch to acting, because funny is all I have; I never got to realize my circusy dreams and was scarred forever with things that involved graceful movement. This girl who barely knew me listened with sympathy and then told me about LAVA. LAVA is an all-female, feminist performance group in Brooklyn and they’re very welcoming of beginners in their classes. My mother, seeing how sad I was about my imploding relationship and life in general, signed me up and assured me that things like taking your entire class to the ground happen only once in your life.

When I got there, I realized that having an all-female space in Brooklyn means you have a heavy queer presence. I found a queer community that got me through my break up, got my body strong, will support me through difficult and dangerous tasks and will reassure me when my confidence is lacking. I found an activity that is my therapy. And I can do a handstand.


And Sometimes You Aren’t Looking for a Girlfriend, But You Get One Anyways

What happens when you have a high self-worth, a good starting place in life that includes a feline and a job, an understanding of the kind of person you want to date and a community that loves and supports you? Well, here’s what happens: you don’t want a girlfriend. You absolutely, no question, don’t want a girlfriend. You want to sleep with someone, you want to fuck. But you Don’t. Want. A. Girlfriend. And then you send a cute girl a quick message about baking mini-pies. She messages you back, and you meet her and you’re still thinking, “But I don’t want a girlfriend. I don’t want to do that again. I don’t have time for one.” But she’s awesome and sane and stable and intelligent and passionate and beautiful and TALLER THAN YOU which never fucking happens because you’re five feet ten inches. She reads with you and listens to classical music with you and takes walks in the park with you and doesn’t mind when you fart. Then when she is cool with you not wanting a girlfriend and sticks around and keeps dating you, you realize you’re already treating her like your girlfriend. So you ask her your to be your girlfriend and you are happy and she is happy and everyone’s happy. YAY RAINBOWS AND HAPPINESS!

It may sound hokey, but online dating on OkCupid has had a good deal to do with where I am today, with the friends I have and with the things I know to be true about myself. The queer community is so spread out and if we think of OkC as meeting place, a queer space, then we can go there to find each other. Interacting with each other isn’t just how we find girlfriends or fuck buddies or people that may hire us, it’s how we learn how to be ourselves. OkCupid taught me how to be gay in the context of community and society.  It taught me how to be a sex blogger, a pet owner, a hand-stander, and, eventually, it taught me how to be a girlfriend. And from all those spectacular failures came some really, really smash-up successes.

Special Note: Autostraddle’s “First Person” column exists for individual queer people to tell their own personal stories and share compelling experiences. These personal essays do not necessarily reflect the ideals of Autostraddle or its editors, nor do any First Person writers intend to speak on behalf of anyone other than themselves. First Person writers are simply speaking honestly from their own hearts.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!

A.E. Osworth

A.E. Osworth is part-time Faculty at The New School, where they teach undergraduates the art of digital storytelling. Their novel, We Are Watching Eliza Bright, about a game developer dealing with harassment (and narrated collectively by a fictional subreddit), is forthcoming from Grand Central Publishing (April 2021) and is available for pre-order now. They have an eight-year freelancing career and you can find their work on Autostraddle (where they used to be the Geekery Editor), Guernica, Quartz, Electric Lit, Paper Darts, Mashable, and drDoctor, among others.

A.E. has written 542 articles for us.


  1. oh. my. god.

    This is the cutest thing, from the handstands to the farts, I am all fuzzy and warm sunshiny for my morning now. Thank You for writing so openly like this!! Not that I’m single at the moment, but if I ever became so, because of this article I would feel like giving sites like these a first chance, and then even more chances. :)

    Very awesome, thank you :)

  2. Definitely think a round of the Ok Gay Cupid Dating Game should make a showing at an upcoming game night with friends.

    This put a smile on my face this morning, thanks. I actually started a new (third time’s the charm, right?) OKC profile once this series began. I don’t know where I am in the dating game, but so far I’ve made fabulous new friendships with some really lovely gals and I have a rad lady penpal and I finally made myself a Tumblr & I guess that’s all pretty good.

    Yay, internet.

  3. This article has inspired me to re-make an OKCupid profile once I get back to the States. (My queer spirit guide also told me I should, so…) I think my problem before was that I had never dated anyone so I was too nervous to actually meet up with anyone. And, ya know, the fact that I had myself listed as straight for the majority of time I was on OKC.

  4. Big-up to Ali for authenticity in this article. Public acknowledgement of farting is the next Big Thing.

    • That is a look that Ali’s cat has never in his life had on his face. Ever. Puck’s expressions tend to range from death glare to satisfaction that the humans are doing his bidding.

      He is an excellent cat.

  5. it’s so so true that there’s so much more you get out of a relationship or even a fling than romance or sex or love or even feelings — even disastrous ex-relationships have introduced me to books or restaurants or writers or Ideas that I’m so grateful for… and the worst ones have provided excellent fodder for my hypothetical memoir!

  6. My first OkCupid date became a story I repeat to make people laugh.

    And then I told it at ACamp Speed Dating and subsequently ‘dated’ Hannah Hart.

  7. I am slightly jealous of the fact that your definition of “OK Cupid Fail” includes sex and a second date in like 3/4 scenarios.

  8. This made me giggle-snort…and people may have stared. But no matter! Because I’ve been having all sorts of smiles after reading this. :D Gives me hope that maybe creating an OkC profile was not a flawed idea after all…

    Cheers to that Ali!

  9. ali this is INCREDIBLE and cute and funny and honest and all that jazz. but for serious, this gives me hope for the world, basically. i think you are very good at this game called life, specifically the okc portion of it. well done <3

  10. I’ve had two OKCupid fails turn into pretty good friends, and Ali, you’re writing (and you yourself) are adorable.

  11. “I ate your pussy, honey. I’m pretty sure that’s gay with a side of rainbows.”

    Yeah, that :) Except I do have to say that I was at the point in life where I simultaneously went down on a girl AND considered myself straight. Like, not even bi, just straight. Which goes to show that some of us have a tremendous capacity for self-delusion….

  12. This article gives me hope because I haven’t had a date on the site ever since I made a profile, 2 cyclesmade one earlier this year, didn’t had any luck. Then just a few months ago, I gave it another go. Still haven’t met anyone face to face. Ehh…I’m on there, that’s something, right? Haha…

  13. My awesomest friends are a girl I met on a dating website… and her girlfriend. Maybe not a dating win, but an overall win. And my biggest online dating disaster has become my funniest story! So yes, the epic fails occur, but I’m glad I used the website.

  14. This is cute. Loving the series! Can we please have one about how to send a message to a cute girl? I’m about to make the plunge into getting an OKC account (I think…yikes!), but I haven’t messaged an anonymous interwebs person since I was in an AOL chat room as a weirdo tween in the early 2000s. Even then I think I was just trying to get rid of some chain email curse. Help with straddling the line between casual nonchalant “maybe we should meet up someday” and omgyoulooksupercuteonlineandwehavethesamefavoritebookletsdate?

  15. Oh this makes me think of my first OKC hookup/summer-thing and it was interesting because in retrospect of our compatibility as friends…. yes, as lovers…fuuuuuck no! It makes me giggle and it makes me realize that I thank her for introducing me to Almond Milk. For real it’s the vegan shit for milk alternative.

    I’ve been alone since then but I enjoy that for various reasons. However when I take that plunge again into OKC and queer dating, I know that I am better informed.

    P.S: I always farted around her when I got somewhat more comfy with her around me.

  16. I’ve had a similar experience, but had a totally different outcome with okCupid. I moved to Utah (I know, I know…) for a girl who I was with for 5 years. Yes, totally U-Hauled it. Anyway, the relationship soured into shit until one day we decided we just couldn’t deal with it anymore. Queue breakup, moving out, etc. Well, I found out that I was stuck in UT because of my job, so I decided to try my hand at online dating with OkCupid. I’m going to go ahead and blame my location because despite messaging a fair number of women who I thought were interesting (but never super awesome) I’ve only been on 1 date that ended in a questionable friendship where I’m pretty sure she only hangs out with me because I buy her shiney things. I made 1 other OkCupid now-questionable friendship with another girl who has been kind of a bitch lately. Finally, I’ve settled for leaving my profile up there for “just friends” and the only reason I leave it up is to recruit girls for a meetup.com group I organize for gay women in SLC.

    I’d say the majority of my post-heartbreak healing has come from meetup.com not OkCupid. Meetup allows you to meet others in your area with similar interests which is a great way to make friends and get out of the apartment with none of the pressures of dating. My biggest issue was that it was hard to meet other gay women in my area, so I helped start a meetup group FOR gay women. Months later, we have 74 members and growing and I couldn’t be happier organizing fun events to do around the area with new friends. I’d highly reccomend it to anyone going through crap times and having bad luck with OkCupid, POF, etc.

  17. Pingback: Elements Of Foreign Brides Examined – United Infra Equipments

  18. Pingback: Revealing Simple Methods In Foreign Brides ~ stickybitz.com

  19. Pingback: Explaining Swift Products In Foreign Brides - Shaffaf

  20. Pingback: Fast Systems In Foreign Brides – The Options – Mariokart Tour

  21. Pingback: Convenient Programs For Foreign Brides – Some Insights – propelorthodontics

  22. Pingback: Rapid Advice Of Foreign Brides Simplified – Mogli.Mobi

  23. Pingback: Compared – Speedy Methods For Foreign Brides – My Blog

  24. Pingback: A Guide To Significant Details For Foreign Brides — bravojob

  25. Pingback: Clear-Cut Foreign Brides Methods – An Introduction | Amurces

  26. Pingback: Considering Products In Foreign Brides – My Blog

  27. Pingback: No-Fuss Foreign Brides Advice – The Options – Arihant Ai (Software)

  28. Pingback: Painless Products In Foreign Brides Explained – Vision Trading

  29. Pingback: No-Fuss Foreign Brides Secrets – Some Thoughts | My Blog

  30. Pingback: Investigating Fast Methods Of Foreign Brides – Yogisha

Comments are closed.