There are many ways to discover that your boyfriend has been questioning his feelings and attraction for you – none of them good.

But I found out in maybe the most dystopian, laughably modern way possible: he’d been asking for advice from ChatGPT.

In our late 30s, we were both looking for the person we wanted to spend the rest of our lives with. Having matched on a dating app, when we first met I liked him instantly.

He was different from other men I’d dated, with ambition that matched mine, a dedication to his interests that I respected, a matching desire to have a family and a levelheadedness that counterbalanced my more emotional whims.

I felt comfortable introducing him to my family after six weeks, and he had introduced me to his in turn.

Yes, we were chalk and cheese in some notable ways – him rigid and logical, me impulsive and extroverted – but we adored each other. Both of us sensed this had the potential to be a serious relationship. We talked about everything.

Or so I thought.

That Friday night, after we’d been together for months, we were laid out on his sofa together. I was working late as he snoozed blissfully on my shoulder when my phone died in the heat of a client exchange about some PR crisis.

Lindsey Hall matched with her boyfriend through a dating app and took an instant liking to him

She thought he was different to other men and introduced him to her family after six weeks

‘S**t!’ I mumbled.

Pivoting, I grabbed his laptop off the floor to run my final, fatigued email response through AI for a sense check.

As I powered up his computer, his ChatGPT – almost poetically – was already front and centre on the screen.

But then, as I copied my email into the dialogue box, I saw it in the sidebar: a past chat titled ‘Relationship issues and uncertainty’.

I stared at the words.

Some will argue that a man is allowed to share private thoughts with a robot, and that I should have ignored the thread. And you’re probably right.

But I dare you to come across your partner’s ChatGPT, see those words, and not click through to read more.

In any case, he’d given me the password for his computer long ago, so it wasn’t as if I’d picked the lock of a secret diary – it was right there in front of me.

While I’m yet to meet anyone who has been in this exact situation, given the increasing prevalence of AI tools in our lives I am sure I won’t be the only one to experience character assassination by ChatGPT.

And let me tell you, there is something uniquely humiliating about coming across someone’s merciless, uncensored stream of consciousness about you – especially when that someone has been kissing you, sleeping beside you, introducing you to their family.

Maybe I’m a tad naive but I think it’s reasonable to assume that a person who has chosen to be with you is happily viewing you in a forgiving light.

Lindsey initially thought the problems would surround her three cats - an issue from the start

Upon discovering his messages, she recognised that the relationship was probably over

That even when you are difficult, messy, neurotic, inconvenient, they are still, fundamentally, on your side.

It’s jarring, then, to be faced with how provisional our place in someone else’s mind can really be.

At first, I clicked on the chat assuming that the focus of his ‘uncertainty’ would be my three cats, which had been an issue from the start.

When we first matched, I had one. But by the time we actually went on a first date, I had acquired two more rescue kittens.

So I was mentally prepared for his usual concerns: too many cats, too small a space, too chaotic a life for a man who prized order and peace.

But the first thing I saw was not cat complaints – if only. It was ChatGPT’s final response: ‘From what you’re sharing, you should consider ending the relationship.’

I froze. That’s not where I thought this was going.

I scrolled up to the beginning.

‘Should I be in love after 3.5 months?’ was how my boyfriend had begun the conversation with his robot agony aunt.

My stomach dropped. The inference of that question was so clearly not in my favour that my hands grew instantly clammy. We’d spent nearly every day together for more than five months by the time I read this conversation – but he’d been having doubts for weeks.

He laid out his concerns about me in clipped, almost clinical fragments: my impulsive lifestyle, my past relationships, my sensitivity, my online writing, my eating disorder history.

And then I saw a sentence that would lodge itself in my brain with the force of shrapnel: ‘Well the cats definitely, and then there’s the whole attraction thing.’

The whole attraction thing.

My ego evaporated on the spot, because if there was one area of our relationship I had felt completely certain about it was that he found me physically attractive. This man’s entire love language was rooted in physical affection, and he was constantly tactile with me.

And yet there he was, questioning what I assumed was the most basic part of wanting to be with someone: their looks.

Lindsey did not come away from the relationship thinking her boyfriend was the villain

He wrote that I was too petite. Too frail-looking getting out of the shower. That my face was pretty but my body wasn’t sexy.

In the beginning my hair had looked damaged, he wrote.

What?! I had been on a beach all summer.

My history of anorexia, which had resulted in residential treatment in 2013 and a near return in 2021, made him concerned about what would happen if I relapsed and he lost all attraction.

It was a train of thought that lacked all compassion or concern; he wasn’t worried for me if I relapsed, only how it would impact him and his attraction to me.

I was, in short, being methodically assessed – but there was no ‘pro’ list to offset the cons.

That was the part that floored me.

He behaved as if he adored me. But it seemed that in the privacy of his own thoughts, I was a set of liabilities.

Then I read the line I think I will probably remember to my grave: ‘I’m just not proud of her.’

He repeated it.

‘…I’m just not proud of her.’

‘Then you should consider ending it,’ ChatGPT guided.

No. Shit.

I wondered how many other times he’d consulted ChatGPT about me.

To my horror, I would find handfuls of other chats dating back to the very beginning of our relationship, when he went as far as to prompt ChatGPT to write a text for him ‘placating me’ about my eating disorder recovery.

Like those who relish in trauma porn, I could not peel myself away from the unfavourable things he was saying about me. From the times, it transpired, he hadn’t had the decency to come up with his own responses to me but instead outsourced it to a robot.

When I was done, I sat there, stunned into a kind of silence I didn’t know what to do with.

This man, I thought, looking over at him asleep on the sofa beside me, resting peacefully against the body he had multiple concerns about.

This man whose family I had met. Whom I had felt almost sure loved me.

This man does not adore me.

It seems this man does not even really like me.

I slid out from under him carefully, and silently gathered the belongings I’d left around his house over the past months. It was eerie how calm I was.

I drove home at 1am, and by the time I got through my front door 20 minutes later the calls and messages had already started.

‘Where are you?’

‘What is going on?’

‘Are you OK?’

I couldn’t answer. Every inch of me burned with humiliation. I would not show him how hurt I was – I had some self-respect left.

I turned off my phone. Half an hour later, his headlights lit up my bedroom window.

By then, rage was beginning to course through my body.

The fact he had used ChatGPT made the whole thing feel even more grotesque and surreal. He hadn’t even had the respect to discuss me with a human being.

If he’d confided in a friend they might have reminded him about the qualities he’d presumably once found attractive in me, or that no one is perfect and everyone comes with baggage.

Or, they might have suggested that if he was having doubts this early then perhaps it was time to end things.

Instead, he’d chosen a robot – predisposed to agree with him, ready to take his cruel thoughts and shape them into something that sounded reasonable.

When he rang the doorbell incessantly, I opened the front door and hissed in a Gollum-esque voice: ‘Get the f*** out of here.’

He looked terrified. Truly bewildered.

‘What is going on?’ he pleaded, his voice shaky. ‘What did I do?’

And when I said nothing, but instead turned my head as tears began to burn, he ran his hands through his hair and fell to his knees in my doorway.

Peering down at him, a part of me wanted to hug him, crouched pitifully, looking so unsure and shaken.

But the words I’d read were on repeat in my head: ‘I’m just not proud of her.’

Finally I said it.

‘I read everything,’ I hissed. ‘I read your whole f***ing ChatGPT.’

His face changed instantly. He looked stricken.

‘Oh God,’ he muttered. ‘No. No. Oh no.’

What followed was entirely predictable: tears, apologies, explanations, clarifications, hours and hours of talk.

He told me over and over he did care about me. That it was more nuanced than it looked, which I’m sure is all true. That he had been confused, scared and trying to sort it out.

That he was attracted to me. That he did not want to lose me. That he was sorry.

At times throughout that night, I admitted I felt terrible for reading his private conversations. But I also explained that I just didn’t understand why he was dating me if these were his inner thoughts.

In my heart, I knew then that the relationship was likely unsalvageable.

But there is something quite disorienting about being wounded by someone and then immediately witnessing their anguish over hurting you.

It turned pain into a shared emotional event, lying in my bed the entire weekend dissecting what had happened. It tempted me into mercy before I’d had the chance to fully recognise my own feelings.

And so, against my feminine intuition, we tried to carry on as we had before.

To be fair to him, he really did try after that.

For the next few months he was nothing but an attentive boyfriend. More expressive. Kinder. More reassuring.

The problem was I knew that beneath the affection, the tenderness and the effort, there had recently been a private record in which I had been repeatedly tallied and come up short.

I knew that somewhere inside his care for me there had been deliberation. Qualification. Massive hesitation.

And once I knew that, I could not unknow it.

After that, every reassurance had an echo under it. Every act of love arrived with a shadow question attached: do you mean this, or are you still trying to convince yourself?

I could stomach his doubts. What I could not do was build a foundation on top of them.

That was, I suppose, the biggest revelation of the whole ordeal: not that he privately had unflattering thoughts about me – I’m sure other exes have thought worse, and I’m fully aware I, too, have had unkind thoughts and unjustified ‘icks’ about people I cared for.

After all, loving someone does not mean being blind to their flaws. I am not an easy person to be with. I suppose no one is, but I am not blind to my defects.

But I do think there is a difference between loving someone despite their absurdities and trying to decide whether they are, on balance, tolerable enough to actually choose.

It is also one thing to suspect that the people who love you also find you difficult, absurd, exasperating, even disappointing at times. It is another thing entirely to read the actual transcript.

Some knowledge alters the chemistry of a relationship beyond repair.

And I ultimately could not bear the possibility that he might have stayed with me anyway. That he might have kept trying, kept sliding further into a shared life, kept reasoning his way through it, maybe even married me and spent decades together – all while some part of him remained fundamentally unsure.

So a few months later, I said what I knew would be true from the moment I saw that ChatGPT conversation glowing on his laptop screen: I would never be able to stop doubting his love.

Through tears and long sighs, I think we both understood.

Ultimately, I don’t come away from this believing he was a villain, or even that he wronged me in some exceptional way. If anything, what made it so painful was how ordinary it probably was.

He was entitled to his doubts – the problem was that I saw them in their raw form, stripped of tact and love’s softening language.

Truthfully, we were probably just not right for each other and it simply bled out into this situation.

The ordered life of a man who prefers to checklist his way into certainty was never going to be a natural home for my hurricane tendencies, my stray cats, my intensity, my desire for novelty.

At this point in my life, I am not asking for a fantasy romance. But I do not want to be chosen by a man who has to continuously talk himself into it.

I do not want to spend my life beside someone who may stay, may even be loyal, and yet remain, in some private chamber of himself, unconvinced.

In the end, I had wandered into the back office of his love for me and found the paperwork. The doubts, the calculations, the small private notations beside my name.

Maybe all love looks less romantic under fluorescent light. But after that, I could not return to the front of house and pretend I had not seen the ledger.

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