Fun things to ask ChatGPT now that it remembers everything

If you hadn’t heard, ChatGPT’s memory just got a whole lot better. Rolled out across the world to Plus and Pro users over the past few days, ChatGPT’s various models can now reference almost any past conversation you had. It doesn’t remember everything word for word, but can pull significant details, themes, and important points of reference from just about anything you’ve ever said to it.

It feels a little creepy at times, but ChatGPT can now be used for much more personalized tasks. OpenAI pitches this as a way to improve its scheduling feature to use it as a personal assistant, or to help you continue longer chats over extended periods of time. But it’s also quite fun to see what ChatGPT can tell you by trawling throughh all your chatlogs. It’s often surprising some of the answers it spits out in response.

Here are a few of things intriguing chats I’ve been having with it, and some prompts to help you find some fu

Note: You will need a ChatGPT Pro or Plus subscription to make full use of this new memory feature, although free accounts with the standard memory function can also glean some interesting answers from these questions.

A note of caution

Although the following prompts will elicit some interesting and often fun responses from ChatGPT, remember that it doesn’t truly know you. If you like what it says, if it makes sense to you, then taking something from that can be truly valuable. Equally, don’t let an AI chatbot tell you who you are — it doesn’t know what it’s talking about. It can’t. But it can give you some interesting responses, as you’ll see.

What’s the first thing we talked about?

This one is a good way to test where the memory function cut off is, and a good reminder how long you’ve actually been using ChatGPT. Mine went back to mid-2024, and pulled out some conversations I had no memory of having myself. That’s not entirely uncommon with conversations I have with real people, but it did remind me how flippantly I have used ChatGPT at times.

Do I want it to remember all of that?

Tell me a story loosely based on me, but set in a fantasy world

This one’s just cool as hell. If ChatGPT knows the kinds of decisions you might make in certain instances (you can even prep if with additional information in the prompt if you want), then having it write a story about you is a lot of fun. You can add your friends and family too if you wish, or insert yourself in your favorite fantasy or sci-fi universe; whatever you like. 

ChatGPT is great at spitting our half-well-written short stories, so why not have the hero of your next prompted creation be you?

If I were a character in a story, what would my arc be?

This one elicist a little more real-world, meta response to the above story writing prompt, but it still captures the essence of the idea. Who are you? Where have you come from? Where does this AI think your story will end? 

It’s a little close to the bone at times, but can deliver some really interesting responses.

Tell me something I might not know about myself

There’s a lot that you can gather from context and ChatGPT knows that better than most; That’s almost all it uses to craft its responses. It’s so good that if you ask it too, it can often pull some interesting insights from things you said or the way you’ve said them over time. The more conversations you’ve had with ChatGPT and the more personal your insights the better, but you might be surprised with what it’ll spit out. 

It gave me some of the insights that previously came out of months of therapy sessions. It wouldn’t have had the same impact as working through my demons myself, but it’s intriguing that ChatGPT can spot things about us without us having to know it ourselves.

What’s something you think I could do with working on?

If you’re keen on self-improvement, there are all manner of things you can do. If you’re already ticking a lot of boxes for personal growth, though, and could use some additional help on what’s next, why not ask ChatGPT for some insight? 

For me, it suggested I be a bit more forthright in what I want from people: Be more explicit. So, can you guys read more of my articles, please? It looks good to my editors. Thanks.

Use our conversations to pretend to be me

This one fell flat when I first tried it, but after a little tweaking and additional prompting, the results wer genuinely creepy. It began to emulate my writing style pretty closely, and though some of the responses it gave to questions I asked of myself were a bit off, it was still a really odd conversation to have.

Not necessarily one I’d want to have again, but interesting nonetheless.

How have I changed over the time we’ve talked together?

If you’ve gone through any major changes over the months or years you’ve been using ChatGPT, it can be interesting to see if your tone has changed, or your energy levels are different. ChatGPT can pick up on that in the way you discourse with it, or how you prompt it over time. Again, it’s pretty dependant on how and how often you use ChatGPT, but the responses can be interesting nonetheless.

Tell me something unsettling that you’ve gleaned from our conversations

If you’re feeling brave, you can ask ChatGPT to tell you something it’s learned about you that might make you feel unsettled. I’m not going to screenshot the response I got on this one or go into any detail, but suffice to say it was an effective prompt with a suitable response. 

What can I ask you to use your new memory features?

If you want even more interesting insights from ChatGPT’s newly elephantine memory, you can just ask it! You might want to explain what the new memory function is, as ChatGPT rarely seems to grasp what its capabilities are, but ask it this question and it’ll give you as many suggestions for how best to use it as you wish. There’s diminishing returns and it’ll repeat itself after a while, but if there’s anything that can give you half-decent prompts to use with a chatbot, it’s a chatbot.