AI Has Entered the (Dating) Chat

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The other day I went on the most disappointing date I’ve been on since I (re)started my single girl journey post-breakup. 

Following the extremely firm directive of my friends, I downloaded a dating app to get myself back into the game (just ONE! It’s so overwhelming I can’t imagine juggling them all at once). I’ve never been an avid online dater before, so this is all pretty new to me. In an attempt to keep myself accountable, I gave myself a loose goal of going on one date each week. That means that in a little over one month into this nightmare adventure, I’ve been on a total of six first dates. 

Of the six, the majority have been obviously bad matches. Not bad men! I’m grateful that at least so far (knock on literally anything wood I can find) I haven’t had any major horror stories. Maybe a few irritatingly one-sided chats in the app itself, but once we get to meeting up in person, every guy I’ve gone out with has been arguably a great catch. Just for someone other than me. 

And that’s what dating is all about! So I refuse to feel disappointed. Especially since one of the six even turned into a handful of dates and had some genuine viability there for a while. But I digress, because what I wanted to talk about was this latest date. Date #6. 

This was the first date from an app that I’d ever been genuinely excited about. We had really epic banter when we chatted on the app. He was proactive in asking me out and making a clear plan. And he didn’t text me too much otherwise in the lead up (I understand that this is a personal preference, but I don’t have any real desire to hear from a guy every single day until we’ve actually met in person and verified that some chemistry exists irl). 

He confirmed our date the morning of with a hilariously witty text. And for the first time in a long time (or at least the six weeks since I got back into the dating game), I was both nervous and excited as I left my apartment to walk to a first date. 

Well, dear reader, I’m not going to sugarcoat things for you here. The date was a dud. It wasn’t a bad date per se. He wasn’t rude or creepy. He remembered that I liked tequila drinks and tried to make a recommendation since he’d been to the bar before and I hadn’t. He paid for said tequila drink. He asked a reasonable amount of probing questions. We played the name game and even found that we knew some of the same people. We had a reasonable amount in common. 

It was just so freaking dull. It wasn’t just that we didn’t have chemistry. It was as if I was sitting across from a completely different human than the one I’d been messaging with. Having little to no vibes irl is a sad truth of online dating. You simply can’t tell if you click with someone until you meet them, and that’s one of the inherent flaws in the model of online dating in the first place. But even in the instances where it’s been immediately clear that I have no chemistry with a guy, I still feel like we’re continuing the banter or at least the general conversation that we had via text. But not this guy. I don’t know who this guy was, but he wasn’t the one who sent those adorably witty messages. 

I was venting about the incongruity of this to a friend a few days later, and he jokingly asked if I thought that maybe the guy was using AI to write his messages before meeting up with a girl. Maybe he knew he wasn’t great at the banter, he argued, so found a way to give himself an unfair advantage. And what’s wrong with that? 

In the world of online dating, the onus falls largely on the man’s shoulders to both start and keep the conversation going. As much as we want to feel like we’ve hit a rebalancing of gender roles in modern dating, 99% of women that I talk to still have a strong preference for men taking the lead. They wish men would approach them (in a respectful way) in person. But if they’re forced to endure dating apps along with the rest of us, they still want to feel pursued. Bumble (the app I downloaded for my initial experiment) has even updated their core ethos of women making the first move to include an option that allows them to pass the baton to the men. 

So it was only a matter of time before AI entered the chat (literally). And I wouldn’t be surprised if men are excited about the possibility of getting a little leg up when it comes to witty banter on the apps. Because whether or not you think it’s fair, men who are funny via text are inherently at an advantage in the world of online dating. It’s nearly impossible to differentiate yourself in the sea of “how was your day” messages (often without a question mark…note for the guys: punctuation is sexy). So if you’re not a naturally witty texter, how can you get yourself noticed? 

From my limited experience, the options for being successful (at least with me) are to be witty, to have specific interests in common that you can jam about together, or to be earnest. 

The idea of being earnest is understandably intimidating for both men and women — we’ve been conditioned to avoid showing too much interest. Being nonchalant has been far too ingrained in our psyches, and I’m personally trying to do my own part in swinging this pendulum the other direction by being genuine and forthcoming whenever possible. And finding common interests can feel like throwing random darts at a wall when all you have to go on is a minimally curated list of prompts on these apps that, let’s be honest, do not encourage being creative or thinking outside the box. 

So that leaves us with being witty. But not everyone is a naturally gifted jokester. And even fewer are talented at the delicate balance of gentle teasing to roasting in the written form. So is AI actually a great solution? 

Apps are — or at least should be — a means to an end, after all. They’re a mechanism to meeting people and seeing if you vibe. A modern day bar or community center. So should we fault men for doing anything in their power to get you off the app and onto a first date irl? I’d argue, as usual, that it depends. In the case of my Date #6, he appeared to be an entirely different human being than the one I’d been conversing with via text. This leads to a level of whiplash that is almost impossible to recover from. But solutions are popping up every day that claim they can maintain your personality and tone, all while helping you keep the conversation going to hopefully land that first date (then, of course, you’re on your own). 

But is it really possible to infuse a genuine human personality into AI conversation? I’m not convinced. But I’m willing to entertain the discussion. Online dating is still a relatively new phenomenon in and of itself. And I personally long for the days where there were more community oriented spaces outside of bars where people might meet irl. Or friends willing to intro you to cool people with no pressure attached. But until we find some other solution, we’re stuck with the apps. And we have to make them work for ourselves. 

What do you think? Have you ever been verbally catfished by someone on a dating app? I’m dying to know if others have had similar experiences. Let’s hear it. 

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