What happened when I used ChatGPT to reply to messages on dating apps

It’s around 10pm on a Monday night, and my friend and I are — for lack of a better word — bored. But luckily after some time sitting around, my friend— who recently broke up with her boyfriend— decides to selflessly redownload Raya, partly to find herself a rebound and partly to provide me with much-needed entertainment.

After half an hour on the app she matches with someone cute who subsequently messages her the following: “Hey (redacted), how are we?”

Since my friend has just got out of a two-year relationship, she’s understandably unsure on what to reply. So she turns to me — her perpetually single friend — assuming I would be able to impart some conversational wisdom.

But unfortunately despite being a writer I, ironically, am terrible at texting and also refuse to download dating apps, preferring to take the role as backseat swiper — all the judgement, without any of the risk of being judged myself.

So, due to our shared inexperience, we decided to consult ChatGPT on what to say. Its first idea: “We? We are absolutely thriving. But you’ll have to keep up if you want to know more.”

I screamed — possibly the worst response I’ve ever seen! We immediately told it to be less cringe, then even less cringe, until it eventually spat out something that was somewhat acceptable.

“Hey, why don’t you tell me.” And to my somewhat surprise it worked! They started chatting and — with a bit of moderation— AI played its part admirably, offering up advice with mixed results.

When he asked her out for Friday, it boldly suggested: "I hope you’re ready to handle me — Friday night’s a yes." However after being specifically told to propose less ‘psycho’ responses, the AI recalibrated and thankfully started suggesting more relaxed messages like: "Yeah, I’ve got some room in my Friday — what did you have in mind?” — which she used.

Eventually, she didn’t need the coaching anymore and was confident enough to reply on her own. Answering the age old question: How many technological advancements does it take to get a date with a creative director.

Later, when I told more friends about this, I realised we weren’t alone. One admitted he used ChatGPT to write his Hinge prompts — which feels like personality catfishing. Another confessed he relies on it to message girls he meets on nights out.

Which made me wonder: are the occasional 2am text I receive actually written by AI, helping decide whether to message “Hey, are you up?” Or “Hey, you out rn?” And if so... should I be using it too?

At this point, when it comes to dating — at least casual dating — ChatGPT has become somewhat of a coach, part ghostwriter, part agony aunt for the anxious twenty-something. I guess like all technological advancements, people will always find a way to use it to get laid.

Still, I resisted the temptation to rely on AI to help my own romantic life. No matter how tragic I was at dating, relying on this program felt like I was cheating. That is until an attractive, single, (and straight) male friend of mine asked me to go see some new play in the West End.

Apparently, he’s been wanting to go for a while but has had difficulty finding someone to join him. Eventually he realised that this is something I’d be interested in — and so asked me. When I told two girlfriends about my upcoming thespian expedition, they were split on what this meant.

One believed that I shouldn’t think too much into it, since his usual crowd of finance bros were not the theatre going type. But the other argued that it was a ploy to get me alone in a dark room. I, myself, was stumped. So, I finally gave in and decided to ask ChatGPT. The AI’s response. “Possibly.”

It told me to look out for the following clues: whether he dresses up, suggests getting drinks after, or seems more nervous/attentive than usual.

On the night in question, he arrived in baggy jeans and a hoodie, told me he had to have an early night, bought me the cheapest glass of red wine and seemed characteristically confident.

During the interval, I discreetly put all this information into ChatGPT. “It’s probably not a date, at least not in his mind.” Ouch! But it was right: at the end of the evening he gave me an awkward hug, before jumping into an Uber headed to his ex-girlfriend’s place.

The worst part of this whole night: the play was far too long and painfully self-aggrandising. But since then, I’ve become converted to the convenience of AI, using these tools as a friendly advisor. Because taking aside its role in our possible destruction, isn’t ChatGPT also just the most unbiased member of the group chat?