Waking up on Sunday morning, well not morning, sleep schedules were for people who hadn’t  been drunk late the night before. Waking up on Sunday afternoon yielded most of the things I expected, a sore throat from drunk karaoke, a greasy horrid feeling caused by a terrible curry at 2am and a pounding headache caused by an ungodly volume of foul beer I could only barely justify buying and drinking.

What I didn’t expect was to check the dating profile I half remembered setting up to find three matches, two of whom had actually messaged me. The latter of those two figures was especially mind blowing. As a guy, one does not simply receive the first message. There is this whole important ritual that must precede any dating app conversation, where you meticulously draft a first message, then redraft it six times, then nearly talk yourself out of sending it, then say ‘fuck it’ to yourself three times and then click send before looking away. You then have to repeat the ritual eight times in order to summon a reply from even one girl you messaged. There is then a mysterious next step I haven’t yet worked out that is required to stop the conversation trailing off awkwardly and thus not leading to a date.

The key part being that a lot of work is required to even get a message, but apparently as a lesbian I’d have recieved two messages unprompted within eight hours of being on the market. I was going to have to reconsider my confidence in the bet, although I suppose the bet had been about matches actually leading to dates, which seemed a distant possibility, there was no way I was going to be able to get a girl comfortable enough to actually agree to go to drinks. Okay, so I hadn’t lost the bet yet, let’s just see what the messages said.

Laura: Hiya cutie! You’re gorgeous! Now, full disclosure, I’m a terrible texter so do you wanna just cut to the chase and go get drinks?

What the fuck? I hadn’t even said anything and she already wanted a date, how come lesbians got to both have lesbian sex and to have this easy a time getting dates, where was the justice? Okay, I suppose homophobia and society at large being shit probably weren’t a very nice price to pay but damn, I’d consider it just for a fulfilling romantic life. If the other message is more of the same I may as well concede the bet immediately.

Ramona: Hey hun, your dog is so cuute, what’s their name?

Okay, less forward but still a very positive start and I could honestly gush about Custard forever. Although that likely wouldn’t lead to many dates, the kind of confident guy girls want to date doesn’t have a dog obsession. Although… a cute girl with a dog obsession is almost certainly a valid way to define wholesome and cute. Screw it, Amy had photos of Custard in her profile, she could be vocal about her dog obsession.

Okay, Ramona first then I’ll work out how to reply to Laura nicely. Just need to try and reply to what she said, compliment her and give her space to continue the conversation. How does anyone find this stuff easy? How did Ramona come up with something as easy and friendly as ‘your dog is so cuute’? She must be a seasoned pro at this. What was the decision making process to decide the appropriate number of ‘u’s? I could see now that two was the correct choice but how did she know in advance? That’s not even getting started on the masterwork that was Laura managing to ask me on a date in the first message without seeming creepy, did someone teach these literary romance wizards or was that just part of the ‘being a lesbian’ package?

Okay, let’s not overthink this… more, just try and get into an ‘Amy-esque’ headspace and see what feels right for me, or uh, her. Hmm, ‘You’re right, she is so cute! Her name is Custard and I’m embarrassingly obsessed with her.’ No, too much crazy dog lady in that, the first part was good? Ooh, maybe,  ‘You’re right, she is so cute! Her name is Custard and as you can see she is the best girl.’ Okay now I just needed to give her something to reply to, umm, her profile mentions books so that could work? I need a lead in from dogs to books though, does such a sentence exist? Okay, not in my brain it doesn’t but I could just ask her anyway, worst case is the conversations stops and we don’t go on a date, which we weren’t doing anyway, so sure! Not overthinking this has gone very well.

Amy: She is so cute! Her name is Custard and as you can see she is the best girl. What books do you like by the way? I read quite a bit of fantasy myself

And send. I should have rethought that, it takes way too big a u-turn mid message. No, stop brain, overthinking post action helps no one, let’s leave that until we know she definitely isn’t replying. Okay, Laura next, what do I say here? Amy would just agree, wouldn’t she? But I can’t stand someone up, so maybe I deflect first and future me can say no for, uh, reasons. Polite and good ones though. Sure.

Okay so uh ‘Well I can’t just agree until I know what cocktails-’ Maybe drinks not cocktails, is that too girly, no, duh, I’m aiming for girly, Amy is a girl and likes cocktails. ‘What cocktails you like and what bar you think makes them best.’ Okay, that was easy enough now I just need to decide about including an emoji at the end. The sentence feels like it could do with one, but is that really needed? Am I too old to use them? Would she think it’s weird? Okay anxiety, you can have this one, no emoji this time.

Amy: Well I can’t just agree until I know what cocktails you like and what bar you think makes them best

Now for the final test, sending a first message to the one who hasn’t messaged me yet, can’t be too difficult, just emulate the vibes I got from Laura and Ramona and stick with the ‘Amy’ headspace, this is somehow marginally less work than usual tinder. Okay, here goes match three of- four? Another one, unreal. Which should I reply to? If I reply immediately to the new girl it’ll look like I’m always on the app and thus desperate, so match four named uh… Penny? Oh god, it’s Penny. Maybe she has to wait a little though, a few hours can’t hurt.

Annddd… she’s messaged me already. Okay, match three can wait instead.

Penny: Hi there, you’re really pretty! Now, what are the three most important things to know about Amy?

Wow, another point for the ‘lesbians have secret flirting classes that make them all smooth as fuck’ conspiracy. And how are they all so attractive anyway? Just gonna blame the LGBTQ-illuminati, no wait, LGBTQAnnon. Okay, now to actually answer her. First, a thankyou, then a compliment, then an answer, three things seemed like a lot though. I can barely manage one, given how little thought I’ve given to the rest of Amy’s personality other than ‘has cute dog.’ But maybe I can offer her that and say- yeah that works.

Amy: Aww, thank you! You’re gorgeous! But if you want three things I’ll need some in return. :P For free, you can have that I have the literal best dog and that I love her an embarrassing amount.

Maybe acting as a lesbian was making me better at this? That honestly looked like a good message from a non-anxious mess. And, in a moment of cunning and genius, I’d tricked my anxiety with a typed out emoji. This was honestly unreal, I was actually having fun, even with overthinking and anxiety. I was gonna lose the bet for sure, but if I could channel even a bit of this energy on straight dating apps after the week was up, then maybe my romantic luck would turn around. A night of buying Ben drinks was an easy price to pay for learning the secrets of good flirting from the art form’s true masters, lesbians.

Rewq

For your second recommendation The demoness of the Hall is a lovely trans story by JAK that I am eagerly awaiting the second part of. Go read it so that you too can wait impatiently!