I turned to ChatGPT to explain why my date went so wrong

‘Let their action determine your next move – not your hope’.

Staring down at my phone screen, I was so relieved to read these words. Trying to find the reason for yet another disastrous date, I had turned to the best source of clear, unbiased advice I could think of: ChatGPT.

Sure, it wasn’t exactly romantic but suddenly the patterns of my dating life were all starting to make sense, and I wasn’t stuck in an agonising mental loop trying to figure it out. 

Two weeks previously, I had woken up in a hotel room, in a foreign city, rigid, shaking and tearful – my nervous system shot to pieces from a day spent masking and being on edge.

My date had just left. I’d asked him if he thought we’d see each other again. 

‘It’s not a hard yes but it’s not a hard no,’ he said. I understood he meant ‘no’.

I’d recently read a book about attachment styles and avoidant men and yet here I was again, rejected. Our first date had been amazing… How had it gone so wrong?

Flashback to a couple of months earlier. I was back on the apps after a two-year break, and was just as bored as I’d been when I used them before. Too many men just wanted to text and never meet.

When a Dutch guy popped up, in town for a few days, I swiped past his profile because of its lack of detail. But, when he bypassed the small talk and suggested a spontaneous meet-up I thought, why not?

I’d been planning on doing a nature hike the next day – he would either be good company or, at worst, good exercise for a couple of hours. I never count first meets as dates and I knew the hiking route was popular and safe.

We arrived almost at the same time and he was easy to pick out from his photo. I wasn’t immediately attracted – but he turned out to be excellent company.

We talked about relationships, psychology and gender roles, careers, crypto, my kids and that fact he wanted children and a dog. When the hike was over, he suddenly kissed me.

‘I just felt like kissing you, so I did,’  he said. It was flattering, though I was mainly buzzing from the mental stimulation that comes from great conversation.

I suggested we meet again that evening and he agreed. Now I was counting it as a date. It was fun to do my hair and feel exhilarated about someone for the first time in ages. We flirted and kissed all night and had genuine, deep conversations. 

Three times he said, ‘Well, if you come to Holland…’ I got home at 5am on a high, faith in dating apps restored. 

We messaged a couple of times throughout his last day and I asked if he’d meant it that I should visit. His answer was a bit of a cold shower: ‘The offer still stands but you’ll have to get an Airbnb’. I talked myself round; I wouldn’t be comfortable in someone’s house after just one date, anyway. 

So I booked a flight and hotel for two months’ time. We texted occasionally in the meantime, which was fine by me. He checked in about my flight and asked if there was anything I wanted to do.

There were some cheesy, sexual messages which were not so fine by me but by then my flight was tied to a work trip and cancelling would have been expensive and complicated.

He picked me up from the airport and he was friendly but not affectionate. I followed his lead but from the outset, I was confused about what the vibe was meant to be. 

Our second date was a long, boring day spent talking, hanging out and going to the cinema to see the new Bridget Jones. He was still an interesting conversationalist but it was completely platonic – he didn’t flirt or touch me – and I was increasingly on edge, trying to work out what was going on while acting like things were fine.

When we left the cinema, he suddenly asked, ‘Would you like me to come to your hotel?’ I said yes, thinking this would be how we got back to what it was like before. But when we got there, he whipped out a packet of condoms – and a sex toy.

‘That’s way too zero to 60 for me,’ I told him. But I was looking for the missing connection and so had sex. He came, I didn’t, he didn’t seem to notice and, shocker, I didn’t feel connected.

Back home, I didn’t expect to hear from him again but, a week later, he messaged to say he thought we should leave it there as ‘an unexpected adventure’.

I wasn’t interested in him any longer but I was keen to understand what the hell happened, and I needed to know how to break my pattern of always being drawn to avoidant men.

Most of all, I couldn’t get one question out of my head: why would he invite me to visit (three times!) and then act completely uninterested and cold?

That’s when I thought of ChatGPT. 

I created a relationship therapist and trained it on attachment styles based on the book I’d read. I fed in a detailed account of both dates and the exported file of our short but, it turns out, revealing WhatsApp chats.

ChatGPT immediately analysed all the signs he was avoidant and not genuinely interested. There were far more of them than I’d seen myself. His spontaneous kiss after the hike, asking if I wanted him to come back to my hotel – both could be interpreted as low-risk, high-reward plays if he wasn’t invested in the outcome.

The big mystery was solved when ChatGPT showed me how I had mistakenly heard a genuine invitation when what he had actually said was ‘vague, polite, and non-committal, designed to keep the moment feeling warm without emotional responsibility […] which he never backed up with: Initiative. A plan. Clear interest in seeing you again.’

It was clear how his non-invitation had dictated everything about the second date. If I’d known, I never would have gone.

Since then, I’ve honestly enjoyed talking about dating with ChatGPT far more than the actual dates. 

I’ve used my AI therapist to unpick two previous disastrous experiences with avoidant men, mentally broken up with an unrequited two-year crush and reformulated my Hinge profile to add emotional depth specifically to repel avoidants.

My profile no longer centres the idea that I’m fun, easy-going and available to hang out as that is catnip to them. I hardly get any matches now, which is great, actually.

I am optimistic, however. Maybe there aren’t that many secure single men out there but at least AI means I will never get caught in an entanglement with one of them again. 

Do you have a story you’d like to share? Get in touch by emailing jess.austin@metro.co.uk. 

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