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I’m single. Is it because I am emotionally avoidant, waiting on a unicorn, or under 6ft tall? Perhaps a spicy meatball of all three?

Or could it be that I haven’t used the magic of AI yet?

As part of my six-weeks-long experiment in which I hand my life over to AI, I decide to use it to help me with my love life. I start by asking it to write my dating profile. So far, my experiment has only led me to experiment on myself, but this time, this will involve another innocent person.

The AI goes to work. “Creative type with nerd firmware and a fondness for novelty: new spots, odd museums, spontaneous plans, niche obsessions. Bring curiosity: I’ll bring the plot twists.”

I squint at it. I sound like a Wes Anderson film.

I scroll through profiles and notice a woman we’ll call A (34 F, SE London). Her profile is mostly pictures of British shorthair cats; she’s also into cat modeling. I’m indifferent to felines, but A is very attractive.

I don’t want to mislead her, so I tell her about my experiment: I’m using AI to help me write my messages. If she fancies meeting, it will choose the date, and I’ll rely on it for conversation prompts.

Unbelievably, she’s fine with this. People more or less do it all the time, she says. At least I’m being upfront.

We arrange a daytime cinema trip. What should I wear? I ask the chatbot. My date has an English degree, so it advises me to wear a turtleneck, dark jeans and boots or minimal trainers. OK.

“Morning! Still on for Marty Supreme?” I text on the day. “Are you more of a trailers-lover or a trailers-hater?” She ignores that, but says she’s coming. She’s a bit rushed, she writes, and didn’t have time to do her nails, but her hair’s looking nice. “Noted. Hair gets the attention today – nails are strictly off-camera. See you 11.20 by the tickets,” I reply.

If uncanny valley was a conversational style, it’s this.

“What was your favourite scene and character?” I ask her immediately afterward, as instructed. She doesn’t answer that, but does suggest lunch. I’ve copy-pasted some AI lines into my Notes app, and refer to them as we walk.

It’s fine to compliment her hair, as she brought it up, the AI advises. I check with her anyway, and proceed.

“That hair has pure A24 energy,” I smile.

“What does that mean?” she frowns.

“She’s asking what that means” I type, turning away. The AI feeds me a quick fix. “Ah – sorry, film brain,” I smile, turning back. “A24 is a studio that makes stylish, indie films. I just meant your hair has that cool, distinctive ‘cinematic main character’ vibe – like it belongs in a film.”

My date points out that I used the word ‘film’ three times in a row.

Over lunch, she tells me about the part of London where she lives. When she goes to the bathroom, I feed ChatGPT the data. It sends me an informed but breezy line to try.

“I heard Baird – the early TV guy – lived in your ’hood for a bit. Feels like the sort of fact a pub quiz would punish you for not knowing,” I smile. She frowns.

“Early TV guy? Do you mean the inventor of the television?”

She’s hit upon a quirk of these AI lines – sometimes they’re weirdly formal, but sometimes the opposite. People can be like that, too. But I’m usually better at conversation than this. “Yes,” I say – as myself.

“When you say AI things, your legs look shorter,” A laughs. She means I’m being stiff, unspontaneous. She levels with me: if someone had sent the messages I have, and she didn’t know about the experiment, she wouldn’t have come today. The messages sound emotionally intelligent, she concedes, yet something’s off about them.

I think about how the AI advised me to bring her a cat sticker or keyring (because she likes cats). One of its prompts was: “Tell me a cat modeling story, I’m genuinely interested!” I didn’t use it; because I don’t think it’s right to say you’re genuinely interested in something, if you aren’t.

The artificial confidence of these lines make them worse than someone who’s honestly nervous, A reflects. “You sound like a therapist who’s been struck off.”

We’re finally having a good time, ripping my AI-assisted personality apart.

“Good luck with the piece,” A concludes, as we finish our tuna melts. “And so you know, I much prefer you to … that other guy.”

AI is great at choosing date ideas. Relying on it for conversation, though, comes at a price of not trusting yourself – your own curiosity, ability to listen, and what you have to offer.

I should say something balanced here, about how AI has its place. But what I really think is that every day we stray further from God’s light, and are doomed.

Rhik Samadder is a columnist, playwright and performer who co-runs the Tuscan Table, a creative writing retreat in Italy