It’s Sunday morning, and Ellen’s boyfriend is staying over. He’s just gone for a shower and he’s left his laptop on the sofa, right there next to her.

And Ellen looks at his open laptop. She touches the touchpad and the screen lights up. And there, amongst his work stuff, is a browser tab called ‘relationship dilemma‘.

She clicks on it. And it’s a long ChatGPT conversation. About her and her intimate past. She can’t quite believe what she’s seeing.

“I know I shouldn’t have looked”

Ellen (not her real name) emailed me about this, and she’s kindly given me permission to share it. I’ve changed the details to respect her and her boyfriend’s confidentiality.

She knows her boyfriend struggles with the fact that she had a couple of casual hookups. On dating apps, a few years ago, before they met. He’s asked her about it multiple times, in an awkward, slightly accusatory way.

He’d been a bit distant that weekend, and she was worried about it. “I know I shouldn’t have looked”, Ellen said.

But she did. She saw her boyfriend telling ChatGPT how bad he feels, knowing about those hookups. That it’s “all he thinks about”. Asking ChatGPT whether he should end the relationship, even though he loves her.

She didn’t have time to read it all. ChatGPT said something about retroactive jealousy. She scanned through looking for anything about her NOW, what was she doing that gave him such a dilemma?

But all she saw was speculation about her past, those hookups, and comparisons with his past and his ex-girlfriend too.

When she scrolled to the bottom, he was telling ChatGPT that her past “outweighs all the positives”. And the AI seemed to be agreeing with him. Maybe what she did was “too much to put up with”.

She clicked off. When he came back, she managed not to say anything.

It’s OK to feel hurt, even if you snooped

What Ellen read was genuinely hurtful.

She’d trusted him with something from her past. And here it was being picked over with a chatbot. In the language of red flags and her being too easy.

She feels bad for snooping. But she also feels judged and exposed. It’s OK for her to feel that, even having snooped.

The retroactive jealousy ricochet effect: now her mind is doing it too

But here’s the line from Ellen’s email that really stood out to me: “this plays on my mind as a massive red flag now.”

Red flag. The same words he was typing, over and over.

This is the ricochet effect retroactive jealousy has between partners. Ellen’s mind is now doing what his does. Replaying what she read. Scanning him for signs. Wondering what it means, wanting to bring it up, not knowing whether to.

And notice the “I know I shouldn’t have looked” part. Usually it’s the other way round.

People struggling with retroactive jealousy go looking on their partner’s phone or laptop, for details or evidence. They find something, and whatever it is, it makes the feelings worse. Now Ellen’s had that experience from the other side of the relationship.

What she actually saw: his rumination, not a verdict

So what did Ellen actually see? A window into her boyfriend’s rumination.

It’s unfair and judgemental, and he probably knows it. In moments of doubt and distress, he’s been unloading onto ChatGPT. His worst fears, his negatives outweigh the positives story.

And ChatGPT went along with it. It hinted at retroactive jealousy, then followed his lead anyway.

That’s what AI tends to do: it works with what you give it. The conclusion that he should probably get out of the relationship is a product of his rumination, not an independent verdict.

So it’s not a reliable reading of how he feels about her. I can’t say for sure what it means, and neither can Ellen. But for her, it’s impossible to unread it, of course.

Should she bring it up? How to start the conversation

That was Ellen’s question really: do I bring it up, or wait and see if he gets past it?

Honestly, retroactive jealousy rarely just fades on its own. And there’s another reason not to sit on it. He’s quietly ruminating and stressing, and now Ellen is too. That’s not sustainable.

So yes, this probably calls for a conversation. A few ideas on how to approach it:

Pick your moment. Not the next time he asks about your past. That’s when he’s in RJ mode, and knowing you’ve snooped will feed it. Choose a moment when you’re both calm and you both have time to talk.

Own how you found it. I looked at your laptop, and that was a breach of your privacy. He’ll probably feel exposed, maybe angry, defensive. Don’t get pulled into a debate about whose behaviour was worse.

Say how it made you feel. Hurt, judged. And concerned for him, because he’s clearly struggling.

Be clear on your boundaries first. This is essential for anyone whose partner struggles with retroactive jealousy. You trusted him with this part of your past, and you can remind him that it’s in the past. But you don’t owe him explanations, details, or ongoing conversations about it.

And to be fair to him, he’s contained a lot. He leaned on ChatGPT rather than on Ellen, and that’s common. A lot of us share our darkest and deepest with AI these days, for better or for worse.

It sounds compulsive, and it very much sounds like retroactive jealousy. But that’s for him to recognise and address.

Is it a red flag? What he does next is the test

So is that chat on his laptop, and his fixation on Ellen’s past, a red flag?

I think the test is what he does when it’s out in the open, after the initial reaction.

Does he own his part of it? Does he recognise it as his to work on, and consider getting some help? Or does he dig in, start cross-examining you about your past, or make it your fault?

That tells you more than anything you saw in the chat.

So for Ellen, and anyone who becomes aware that their partner is quietly battling with retroactive jealousy: if you have that conversation, go in as a supportive partner who wants the best for you both. And see if he or she meets you in the same spirit.

If you’re the one asking ChatGPT about your partner’s past

And if you’re in her boyfriend’s situation, and maybe you’ve typed your partner’s past into ChatGPT looking for assurance or some steer on how to handle it, I want to say something to you too.

This is a sign that you’re stuck and struggling. You’ve been carrying this on your own, and trying to think and chat your way out of it, and it’s not working.

That’s not a failure on your part; it’s how retroactive jealousy gets you. You’re not alone and RJ is treatable.

Thanks again to Ellen for sharing, and I hope this is helpful for you.