I used ChatGPT AI for dating and here’s what happened

We’ve all heard the warnings: AI could end up replacing us as it becomes increasingly capable of doing … well, everything.

With the introduction of AI tool ChatGPT, we’ve opened a new realm of possibility when it comes to the written word. Whether it’s cover letters, speeches, or even what to write in a Valentine’s Day card, ChatGPT has managed to make some of the most tedious tasks easy. After all, what says we’re living in the future like an hour-long chore becoming less than a minute of typing into an AI prompt.

Unfortunately, I’ve found one thing that ChatGPT cannot do – help me find a date.

Typically, my online dating attempts can be characterised as slightly awkward, frequently sarcastic, and extremely boring. “Hey, how is your week going?” is my go-to introduction, which we can all agree needs to be replaced.

On Valentine’s Day this year, which would turn out to be my bleakest holiday of love yet, I turned to ChatGPT for alternatives. Surely AI, with the entire internet at its virtual fingertips, would be able to help me secure a date, or at least engage in more interesting conversations than the ones I’d been having on Hinge and Bumble.

The first match on my dating agenda was Kyle* a 30-year-old who wrote on his profile that he was looking for a relationship.

Eager to test out what I assumed would be the key to romantic success, I typed out a prompt to OpenAI’s ChatGPT. “Write me a general introduction message to send to my Bumble match.”

In response, it suggested the message: “Hey Kyle, I’m Chelsea! I came across your profile and was immediately struck by [something you found interesting or have in common with them]. I’d love to chat more and get to know you better if you’re interested. So what’s been the highlight of your week so far?”

I couldn’t believe it. Not only was it just a longer version of my go-to opening message, but ChatGPT had managed to make me sound like someone’s 50-year-old uncle on Facebook.

I asked ChatGPT to try again, this time clarifying that I wanted a “general,  but funny, opener to a conversation”.

The response? A karaoke date.

“Hey Kyle, I’m going to cut to the chase: What’s your go-to karaoke song? I need to know if we’re going to be compatible or if we’ll need separate karaoke nights with our friends,” the AI suggested, before noting that it was confident the message was “light-hearted and playful,” and that it “offered a specific question to start a conversation”.

I wasn’t convinced, as the message sounded like it was written by a robot, and because I actually hate karaoke, but I sent it anyway.

To my surprise, Kyle actually came back with a response, and a normal one at that. According to my Bumble match, his favourite karaoke song is “Eye of the Tiger”. He followed up by asking me about my go-to.

My doubts about using ChatGPT for online dating were confirmed when I asked it to write me a response to Kyle, and it offered an even more absurd message.

“‘Eye of the Tiger’ is definitely a classic choice! But when I’m feeling really brave, I like to go for ‘Bohemian Rhapsody’. It’s always a crowd-pleaser, and I’m a big fan of any song that involves headbanging. What do you think? Are you ready to rock out with me at karaoke sometime?” the suggestion read.

I, of course, had no intention of sending that to Kyle. Feeling brave? Headbanging? What was this, my first time interacting with another human being ever?

I asked ChatGPT to try again, at which point it came back with the slightly more acceptable response: “‘Eye of the Tiger’ is definitely a classic choice! But when I’m feeling really brave, I like to go for ‘Livin’ on a Prayer’ by Bon Jovi. It’s always a crowd pleaser, and I’m a big fan of any song that involves belting out the chorus. What do you think? Are you ready to sing some Bon Jovi with me at karaoke sometime?”

Again, clearly not a response I would send. We’d exchanged one message, why would I already be inviting Kyle to karaoke? After some back and forth, ChatGPT and I finally settled on the last sentence: “Are you a Bon Jovi fan yourself?”

I didn’t expect to hear back from Kyle. After all, I certainly wouldn’t have answered if I were in his shoes.

“Ooh those are some great choices! Bon Jovi is pretty awesome, but I really only know a few of his songs,” Kyle responded along with a laughing face emoji.

Thankfully, ChatGPT toned it down, with the AI suggesting I thank Kyle for the compliment, and ask him what kind of music he usually listens to. As a follow-up, I also asked him if he’d be interested in getting a drink soon. He never answered.

No matter, with a few more Bumble matches to try, I turned my attention to Chris*, a 33-year-old living in New York, who wrote on his profile that he liked exploring all that the city has to offer. According to Chris, he enjoys spending time outside with his dog, and is looking for someone smart and unique.

ChatGPT was immediately interested, with the AI offering a lengthy introduction to send.

“Hi Chris! I saw in your profile that you love exploring all the amazing things NYC has to offer! I’m always up for an adventure, whether it’s trying a new restaurant or checking out a cool art exhibit. What’s been your favourite NYC discovery so far? And what kind of unique experiences are you looking to share with someone special?” I asked per ChatGPT’s suggestion.

The message was a far cry from what I’d usually send, as I typically avoid any hints of earnestness. But maybe ChatGPT was identifying my dating app flaw? Perhaps these candid messages were what I’d been missing.

And, as a colleague had noted after I’d informed him of my experiment, ChatGPT’s responses “couldn’t be any worse than [my] current game”.

“Maybe it’ll work,” they’d added assuredly, before joking about the prospect of one of my matches falling in love with the AI.

Chris seemed slightly guarded in response to my drawn-out message. “I’m not sure what my favourite discovery would be. Probably something along the lines of food haha,” he wrote, before adding: “I’m looking for someone who can go hiking or to the opera or just sit in the park on a sunny day.”

“I’m always down to try new restaurants or cuisines!” ChatGPT told me to reply with, despite saying something similar in my first message. According to the AI, we drew the line at the opera.

“And I love getting outside, whether it’s for a hike or just a leisurely stroll through the park. The opera might be a bit of a stretch for me, but I’m definitely open to new experiences and learning about your interests. What’s been your favourite outdoor spot to explore in the city so far?” the AI-generated message continued.

According to ChatGPT, this was the perfect thing to say because it responded to Chris’ interests in food and outdoor activities, and also showed that I’m “open to trying new things”. The AI also reminded me to keep my tone “friendly and genuine”.

As with each of its previous messages, ChatGPT ended with: “Good luck!” It clearly felt I needed it.

To try this experiment, I needed to ignore any discomfort I had about sounding too eager. However, that doesn’t mean I wasn’t fully aware that I was coming across as overzealous.

Fortunately, Chris seemed somewhat open to matching my AI-generated energy. “As long as you’re willing to try something once, that’s good with me,” he said, while telling me he liked to take his dog for walks in a nearby park.

I made the mistake of telling ChatGPT I love dogs.

“That’s so cool that you live by [redacted] and have a dog. I’m a big dog lover myself!” I wrote, before revealing where I live and suggesting that we “meet up at one of the parks sometime”.

“I’m always up for a picnic or a walk with some furry friends,” I continued, to my mortification over the use of the phrase “furry friends”.

Although I sent the response, I tried to reason with ChatGPT. “Can you give me a response to say in a cool way?” I begged the software. “I don’t want to use the phrase furry friend.”

The “cool” alternate response came back: “Ah, so you’re a proud companion of a four-legged cutie, I like that. What’s your pup’s name?” Immediate no.

Chris then told me about an upcoming day trip he had planned, his love for the beach, and to ask whether I had any restaurant recommendations in my area. He carefully ignored my suggestion that we “meet up”.

In response, I (ChatGPT) again over-enthusiastically praised everything he’d said, while telling him that I too love the beach because “there’s nothing better than feeling the sand between your toes!”

After telling ChatGPT the names of two of my favourite restaurants, it added: “As for Korean BBQ, I highly recommend Jongro or Five Senses. Both have amazing meat, and the atmosphere is always lively. Let me know if you end up trying either of them, I’d love to hear what you think?”

It’ll come as no surprise that I never got a response back.

Apart from Kyle and Chris, the rest of my Bumble matches were not impressed with my AI-generated opening lines.

“Pizza is definitely one of my favourite foods too! What’s your go-to topping?” I asked Kevin*, who chose to ignore the message.

To Fred*, who’d written on his profile that his “personal hell” was “small talk on dating apps,” ChatGPT was confident it had the perfect introduction.

“Well, lucky for you, I’m not a fan of small talk either. So how about we skip the pleasantries and dive right into an interesting conversation?” Not only was my message the opposite of interesting, it managed to make me sound exactly like I was about to engage in small talk.

At this point, I suggested to ChatGPT that maybe a fun joke would be a better way of starting the conversation.

“What is a funny joke I can send to my Bumble match as a conversation starter?” I asked, to which ChatGPT responded: “Why did the tomato turn red? Because it saw the salad dressing!”

After I requested an alternative joke, ChatGPT came through for the first time all night. “Why don’t scientists trust atoms? Because they make up everything!” It was cute, simple, and, I thought, worthy of a response.

Unfortunately, David* didn’t share ChatGPT and my sense of humour. Although he’d asked why when I’d sent the first line of the joke, he was ultimately unimpressed into silence by the punch line. His loss.

In a last-ditch effort to turn my online dating around with the help of ChatGPT, I opened up Hinge, where I’d gotten a message from a man who’d surmised that I seemed “fun, spontaneous, and adventurous” from my profile, which are qualities he said he “always appreciates in a woman”.

His message, which sounded, to my amusement, exactly like the ones ChatGPT had been crafting for me, continued: “Normalcy is so overrated. If I bumped into a group of your friends on the way to meet you for the first time, what would they tell me to expect?”

It wasn’t an opener I wouldn’t usually reply to, because, as I mentioned before, I try to steer clear of effusive messages. But, maybe coming up with a response to a unique message such as this is where ChatGPT would shine. And maybe, by opening myself up to individuals who were clear and direct about what they were looking for, I’d be able to find my match.

It turns out that ChatGPT has no place in the dating world, as it managed to craft a reply so bizarre and embarrassing that I refused to send it.

“They’d probably tell you to buckle up and get ready for a wild ride! But in all seriousness, they might mention my love for trying new things, my spontaneous streak, and my contagious laugh. But you’ll have to find out for yourself!” ChatGPT suggested I say in response to David.

Rather than send the message, I replied to ChatGPT: “Can you make that sound cooler?”

“Sure! How about this: ‘Thanks for the compliment! My friends would probably tell you to expect a wild and unpredictable ride, with plenty of laughter and excitement. Normalcy is definitely not our thing. So buckle up and get ready for some fun!” the AI software came back, with ChatGPT bewilderingly doubling down on the insistence that my Hinge match “buckle up,” as if I were a professional bull rider rather than a journalist.

I ended Valentine’s Day the same way I’d started it, with no dates, and with a renewed insistence that there has to be another way to meet potential partners than dating apps.

However, I will say that ChatGPT’s failure to secure a date slightly mollified my own dating app insecurities. At least I was better than a robot.

*All names have been changed and I apologise to anyone I matched with yesterday.