Horror Stories: Dating While Gay
Updated: Sep 8, 2018
Read this and laugh at me. I know you want to.
As a general rule, I don’t talk much about my dating life to friends and family. Most people probably think that’s because I like to keep to myself, but it’s really because I want to protect them from suffering like I did. Nabbing a date as an admittedly somewhat picky gay male sometimes feels like trying to paint the Mona Lisa with a shoelace. Nabbing a good date, then, is nearly impossible.
So I tend to keep to myself, unless I have that rare reason to share a victory.
But with this post I want to regale my readers with fantastic tales of dates gone wrong. There’s drama, there’s intrigue, there’s mystery - but above all, there’s horrible awkwardness that will make your skin crawl and have you clutching your face in sympathetic agony… Okay, it probably won’t be that bad for you. But it was for me.
I’ll start with an easy one. His name was Reginald (not really - I am going to make up the names of the men in this post to protect their privacy and also because it’s fun to make up ridiculous names). We met on Tinder - that’s how all these stories begin. Welcome to the gay experience.
Anyway. Reginald and I matched on Tinder when I was in college. I thought he was cute in his pictures and he was a decent conversationalist, but I certainly wasn’t head over heels. He suggested we meet up at the mall, and I had no idea what I was doing, so I said “sure.” Most people reading this are probably thinking you met at the mall for your first date? To which I say: I know, I’m an idiot, thanks.
As soon as I saw Reginald standing next to a pillar at the mall in the middle of a busy crowd, I knew I made a mistake. There was nothing wrong with him, but he gave off such an awkward vibe that I could feel it from across the food court. I think we hugged when I approached him, but I don’t really remember because I blacked out. We then had an uncomfortable exchange of words about where we should go, since we had no plan other than “let’s meet at the mall.” Genius.
So, we ended up sitting outside of Sbarro at a table in the food court, staring at each other. I’m not exaggerating. We literally just sat there and looked at each other. I would occasionally ask him a question like “what’s your major” or “how do you like school,” to which he would give a one or two word answer and then shut down. He seemed nice and I could tell it was because he was nervous, but I physically could not stand it.
After ten minutes of this, I did what any sane person would do and pretended to get a phone call from a friend. “Oh my god, you need me to pick you up? Are you okay?” I said into the phone. Reginald couldn’t even break out of his nerves for long enough to look concerned - he just continued to stare at me blankly. I told my imaginary friend that I’d be there soon, then “hung up” the phone. I serenaded Reginald in numerous apologies, which he accepted stoically, then I ran out of that food court faster than you can say “Reginald.”
We never spoke again.
Then there was the guy in college who, at the time, I thought I was head-over-heels for. Looking back, the fact that I thought this is horribly embarrassing. But I was naive. I still am.
His name was Ostello. He was one of the ten gay people who actually went to my college (I’m exaggerating, but sometimes that’s what it felt like). He was a year younger than me, and the only thing he was more obsessed with then opera music was himself. Our first date was at a coffee shop and I was totally smitten. He was cute and we talked for four hours over lattes.
At the time, I thought talking for four hours was a sign of some magical chemistry. Looking back on it, I realize it was a sign of Ostello’s incredible ability to talk about himself, and my incredible ability to listen and smile in silence. I think I learned more about opera music and Ostello’s contributions to the craft in that four hour period than I ever cared to know in my entire life. And yet - because he was cute, and because I was desperate, we went on a “second date.”
This date turned out to be my first (and only) experience as an Uber driver. The plan was to grab dinner at the local Chipotle (so romantic, I’m still swooning). I was going to pick Ostello up, since he didn’t have a car on campus. He texted me at the last minute and asked me to pick him up from one of the academic buildings on campus, since his class ran over. So I did.
When he got in the car, Ostello gave an apologetic little speech about how he would love to get dinner, but he was just so busy that he didn’t think he could tonight, so could I maybe just drop him off at opera practice? I, being shy and nervous and too nice to do anything else, agreed. I drove him 10 minutes across campus to his (surprise? Unplanned?) opera practice, he got out of the car, and we never spoke again.
At the time, I chose to be upset about this experience for a month. Now, though, I choose to send big fuck you vibes Ostello’s way, and to realize that I’m a good person who deserves more than to be an Uber driver for men who I’m supposed to be on a date with.
The last one isn’t even a bad date, technically, since we never met. It was another Tinder match, this time post-graduation. His name was Scabbers.
Scabbers and I had the rare sort of Tinder chemistry that only comes around once in a blue moon. He was cute, he was in medical school, and our conversation flowed as smoothly as a river and as sweetly as honey. Everything felt natural and easy and good.
We chatted for a few weeks on Tinder, both of us having a great time and never having to force anything. I was getting a little bit impatient, because I kept suggesting that we meet and he kept suggesting that we wait because he always had other commitments. At one point, I put my foot down and basically told him it was pointless to keep chatting so much if we were never going to meet. I was trapping little Scabbers in a corner.
That’s when Scabbers unveiled his trump card. He said “I have scabies.” Knowing Scabbers and our witty banter, I naturally thought he was joking. I made some remark about how I thought that was a disease pirates contracted in the 1600’s. But then he told me he was serious. And I was kinda like… okay? We were supposed to get coffee, so I was unsure about why this disease was relevant.
Then Scabbers started going into detail about where the scabies was, why he contracted it, how he was treating it, when it would be cured, etc. I felt like a health clinic. Suddenly I lost my appetite for coffee, and my appetite for a date with Scabbers. Looking back on it, maybe Scabbers was a catfish and he had to get out of meeting me - but I really don’t think that was it. I think he was trying to be honest about something and he came off as maybe a tad (or, like, a lot) too honest. In the grand scheme of things, Scabbers wasn’t so bad - just… strange.
I still don’t know what scabies is. Nor do I want to know. Don’t enlighten me if you know. Thanks.
I have more bad date stories, but I’ll stop there. These are the highlights. I don’t want to bore you with the minutiae of my personal disasters. If you have bad date stories of your own, I’d love to hear them. Send them to me at firstname.lastname@example.org. Maybe I’ll even post them.
Let’s suffer together.
This post is brought to you by Lucky Escape by Years & Years, because it’s by a gay artist and I love it and the title of the song reminds me how lucky I am to have escaped the men in the stories I just told. It’s been added to my blog playlist, which you can download on both Spotify and Apple Music. Enjoy.
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