This essay was adapted from the newsletter Lindsey Hall Writes. Subscribe here.
I found out my now ex-boyfriend had been questioning his feelings and attraction to me in the most dystopian, laughably modern way possible: ChatGPT.
Lying on his couch on a Friday at midnight, I was working late as he snoozed blissfully on my shoulder when my phone died in the heat of a client exchange.
“Shit,” I mumbled. Pivoting, I grabbed his laptop off the floor to run my final, fatigued glassy-eyed client response through A.I.
As I powered up his computer, his ChatGPT, almost poetically, was already front and center on the screen.
As I copied and pasted my email, I peered to the left side of the screen, and that’s when I saw it in the sidebar: a past chat titled “Relationship Issues and Uncertainty.”
I stared at the words.
Now, here is where I am certain many will piously tell me I dug my own grave. I invaded his privacy. That I never should’ve read what I read. That the man is allowed to share private thoughts with a robot.
And of course all of that is true.
But I dare you to come across your partner’s ChatGPT, read those words, and not unravel all moral senses.
And, let me tell you, I wish that I had never read what I did. If only because 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 family, and making you feel chosen.
All of us who embark on the quest of love move through relationships and intimacy believing, maybe a tad foolishly, that a person who has chosen to be with you is happily viewing you in a forgiving light. That even when you are difficult, messy, neurotic, inconvenient, they are still, fundamentally, on your side. It’s jarring to then be faced with how provisional our place can really be in someone else’s mind.
At first, I clicked the chat, assuming, with mounting annoyance, that the focus would be on my cats.
Three cats had been an issue from the start. When we met, I had had one. But by the time we actually went on a first date, I had acquired two more. The rescues had happened in Montenegro, which had the roughest stray culture I’d ever seen. Two kittens looked at me with sickly eyes, and suddenly I became Florence Nightingale with a litter box.
So I was already mentally prepared to roll my eyes at his usual concerns: too many cats, too small a space, too chaotic a life, too much long-term feline commitment for a man who prizes order and peace and clean surfaces.
“Oh, for the love—” I was basically muttering as I clicked.
But the first thing I saw was indeed not his cat complaint. It was ChatGPT’s final response.
“From what you’re sharing, you should consider ending the relationship.”
I froze.
Oh.
That’s not where I thought this was going.
I scrolled up to the beginning.
“Should I be in love after 3.5 months?” my boyfriend began the conversation to his robot Freud.
My stomach dropped: The inference of that question was so clearly not in my favor that my hands grew clammy instantly.
Doing the math, we were nearly six months in by the time I read this conversation, so immediately I understood that this chat had happened weeks ago. Beside me, a line of drool slid down his cheek as he slept, warm and peaceful, against the body I would soon learn he had been privately workshopping concerns about with a robot.
I kept reading.
The conversation, as I’d understand soon enough, would not go any better for me. Short sentences of nearly entirely unfavorable comments. He laid out his doubts in clipped, almost clinical fragments: my lifestyle, my sensitivity, my past, my van, my online writing, my eating-disorder history, my cats. And then I saw a sentence that would lodge itself into my brain with the force of shrapnel: “Well the cats definitely, and then there’s the whole attraction thing.”
My ego evaporated on the spot.
Look. It’s not that I think I’m a dime—I’m a realistic lady—but this man’s entire love language was rooted in physical affection. It was quite literally the only type of love I felt certain of from him. It was the category in which I had felt the safest. Of course, as an intuitive woman, I had already felt some of his other uncertainty. But this was the one thing I had not questioned. I reread it over and over.
And yet there I was, inches from him, reading that in the back of his own mind, he had been questioning what I assumed was the most basic part of wanting to be with someone—their looks.
A few lines later came the comments about my body. I was too petite. Too frail-looking getting out of the shower, he had noticed once. In the beginning, my hair had looked damaged. (This one made me extra salty. I had been on a European beach all summer; I needed a keratin treatment. Christ, give a girl a break.) My history of disordered eating had made him worry what would happen if I relapsed and he lost all attraction to me.
I was, in short, being methodically assessed, only there was no “pro” list.
That was the part that floored me.
Not that he had concerns about my body or my past or personality, though that felt awful enough. But that, in the privacy of his own thoughts, I was not being held in the warm and forgiving light I had imagined. I was not someone he adored. I was a set of liabilities. A ruminating amount of concerns. An accumulation of negative variables to be sorted and weighed and dissected through, and alarmingly easy to summarize (or so it felt).
There is something existentially jarring about seeing yourself rendered that way through someone else’s eyes. You become suddenly, humiliatingly aware that you are simply another person in the world. Not the heroine of a rom-com, not the sum total of your intentions and tenderness, but a body and a history someone else may find embarrassing, inconvenient, or hard to love.
Then I read the line I think I will probably remember to my grave:
“I’m just not proud of her.”
He repeated it with three dots.
“… I’m just not proud of her.”
“Then you should consider ending it,” the chatbot urged.
No shit.
As I finished reading that, adrenaline running through me, I wondered: How many of these conversations are there?
To my horror, I would find plenty.
I could not peel myself away from the unfavorable things documented.
When I was done, I sat there, stunned into a kind of silent vacancy. I was too shocked for coherent thinking and too confused to feel anger.
This man, I thought, looking over at him asleep beside me. This man whose country I had just visited, whose family I had met, who, after nearly six months, 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, gathered my shoes and charger and the little belongings I’d left around his house over the months, and packed them into my purse in silence. It was eerie how calm I was.
I left without a word.
I drove home at 1 a.m. in total silence, and by the time I got through my front door, the calls had already started.
Where are you?
What is going on?
Are you okay?
I couldn’t answer. Every inch of me lit with humiliation. Every prideful cell in my body writhed in anger and shame. I would not show how hurt I was to this man. I did not want to offer him the intimacy of watching me react to what he had written.
I turned off my phone.
Half an hour later, his headlights lit up my bedroom window.
By then, the rage I’d initially stifled was now beginning to ripple through my body.
The fact that this had happened on ChatGPT, in its own way, made the whole thing feel even more grotesque and surreal. It was like accidentally reading someone’s diary, except the diary was predisposed to agree with him, ready to take his cruel thoughts and shape them into something that sounded reasonable.
I flinched, wondering how much he must’ve been mentally suffering with his concerns about me that he felt he needed to use A.I. to decipher them.
I was all-around horrified. And after he started ringing the doorbell incessantly, I opened the front door and hissed, in a Gollum-esque voice: “Get the fuck out of here.”
He looked terrified.
“What is going on,” he pleaded in my doorway, his voice shaky. He paced back and forth. “What did I do?” he asked over and over.
And when I said nothing, instead turning my head as tears began to burn, he ran his hands through his hair and fell to his knees, grasping on to mine tightly.
In that moment, I had the strangest flashback, déjà vu.
Years earlier, a different boyfriend had left me in a different house. Our neighborhood was under a fire-evacuation warning, but he had still wanted to go to a forest rave with friends. Emergency sirens down the street, smoke on the hill, and this absolute buffoon gave me a hug goodbye and peeled out of the driveway to go do party drugs in the woods with no Wi-Fi.
I had left that boyfriend in a similar manner. Eerily calm and resigned. Once the fire warning ended, I waited till morning, when I knew our friends would soon be back to pick up their dogs, and I grabbed our cat, packed everything I owned into my Honda Accord, left a note that I was done, and walked out. I disappeared to a hotel nearby, responding only to a roommate to let her know I was fine but did not want to speak to him.
When I finally chose to text back, many pleading texts later, he arrived at the hotel unshowered, unkempt, a sobbing mess, and he too had crumpled to the floor, clutching at my knees and begging for forgiveness through muffled pleas for our cat, who remained judgmentally staring from the hotel window.
Now, watching yet another man unravel, I felt not just hurt but haunted by recognition. At least this time I was on my own porch.
How many times, I wondered, does a woman have to stand in the aftermath of a man’s lack of emotional wherewithal and then be asked to comfort him because the consequences have become real?
I peered down at him.
A strong man, a brilliant one too. Respected by the community, admired by many, including me.
How scared and childlike he appeared in this situation. How unsettling it was to see him disoriented.
A part of me wanted to hug him, crouched pitifully, looking so unsure and shaken.
But the words I’d read repeated themselves like banner ads.
Finally, I said it.
“I read everything,” I hissed. “I read your whole fucking ChatGPT.”
His face changed instantly. He looked stricken. Horrified. Instantly ashamed.
His shoulders slumped. “Oh God,” he muttered. “No. No. Oh no.”
Against my feminine intuition, we tried to continue dating. This is the part I judge myself for, just as much as for snooping.
You can probably guess what happened: tears, apologies, explanations, clarifications, hours and hours of talk. He reiterated that he did care about me. That it was relationship anxiety. 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. That it was more nuanced than it looked. I’m sure that’s all true.
But in my heart, I knew that night that between me violating his privacy and the depth of the criticisms he wrote, the relationship was likely unsalvageable. There is something quite disorienting about being wounded by someone and then immediately witnessing their anguish over hurting you. It blurred the edges of my reality. It turned pain into a shared emotional event, after which we spent the entire weekend lying in my bed, dissecting what had happened.
To be fair to him, he really did try. For the next few months, he was nothing but an attentive boyfriend. More expressive. More deliberate. Kinder.
But the problem was no longer what he had written.
The problem was that I knew what he had once thought—unfiltered.
I knew that beneath the affection and 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 hesitation.
And once I knew that, I could not unknow it.
After that, every reassurance had an echo under it. Every compliment felt slightly unstable. I could, and do, forgive his doubts. What I could not do was build a foundation with someone on top of them so early in a relationship.
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 said worse, and I’m fully aware I, too, have had unkind thoughts about people I cared for.
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 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. It removes the protective blur that makes intimacy obtainable.
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 had a whole few decades together—all while some part of him remained fundamentally unsure and he just never quite chose otherwise.
That, to me, felt intolerably lonelier than being alone again in my 30s.
So, a few months later, in my car, after I had arrived 20 minutes late to our date (I had inadvertently started “punishing” him with behavior like this), I said the thing I had known would be true from the moment I saw that ChatGPT glowing at me from his laptop screen: I was never going to stop doubting his love. And I had checked out.
In the end, I had wandered by accident 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 this is ordinary. Maybe all love looks less romantic under fluorescent light.
But after that, I could not return to the front of the house and pretend I had not seen the ledger.
