Try this before you finish your coffee: open ChatGPT, ask it who quietly disappeared from your life, and see if you’re ready for the answer. That’s the exact test a Redditor named Professional-Rest138 ran recently, and the result apparently knocked them sideways. The trigger is OpenAI’s new Apple Messages plugin, released August 20. It can dig back through years of your texts the second you give it permission.
Nobody was tracking who slid out of their daily rotation or who kept texting first for months while getting silence back. Now something can pull the receipts. This Redditor tried it and came back with a truth their own memory never flagged.
🔍 How To Run It
- Turn the plugin on. This only works on a Mac with Apple silicon (M1 or newer), through the desktop app, not the browser and not iPhone. Open the sidebar, go to Plugins, search “Messages,” and enable it. macOS will ask for Full Disk Access since the plugin reads the Messages database already sitting on your machine. The free plan covers this.
- Test it on something boring first. Don’t point a brand new memory feature at anything sensitive on the first try.
Search my messages and tell me the last five people I texted and roughly what each conversation was about. Do not send anything, just tell me.
If that comes back accurate, you’re clear to run the real question.
- Ask the question that actually matters. This is the prompt the original poster used, word for word.
Look at my whole message history and tell me the truth. Who do I talk to most, and has that changed over the last two years? Who used to be in my daily life and has quietly dropped out of it? Who messages me far more than I message them back? Be honest, not kind.
Notice the phrasing. “Be honest, not kind” is doing the heavy lifting here. It’s a direct instruction that blocks the model from softening the answer. It also forces a comparison across a two-year window instead of a vibe-based guess.
- Turn the answer into action. The follow-up prompt is the one that actually changes something instead of just making you sad.
Based on that, who are the three people I should message this week, and what should I say to each of them? Draft all three.
That’s a two-part prompt. The first half forces a decision from open-ended data instead of leaving you staring at a list. The second half hands you a finished draft, which kills the “I’ll message them later” excuse before it starts.
What The Results Actually Mean
People running this report back two patterns. Some find a friendship they let fade without noticing, someone who used to text daily and just stopped showing up in the thread. Others find the reverse: a person who’s been carrying the relationship, texting first every time, while they’ve been the one going quiet.
Neither answer is comfortable. That’s the point of asking a machine that doesn’t care about your feelings. It runs the numbers instead of your memory, which edits itself to protect you.
The original poster suggests doing this on a Sunday with coffee, not squeezed into a lunch break. That’s good advice. This surfaces something more real than it looks like on the surface, and rushing it defeats the purpose.
⚠️ Before You Turn This On
A few things worth knowing before you flip the switch.
💡 No Mac, or only an iPhone? You can still run the drafting and gut-check prompts. Just copy a conversation thread and paste it in manually. Only the “search my whole history” version needs the actual plugin.
💡 It can send messages as you. There’s an approval screen by default before anything goes out, and yes, there’s a toggle to turn that off. Leave it on. That approval screen is the only thing standing between you and an outgoing text you’d have to explain in person.
💡 Not everyone loves this idea, and the comment section made that clear fast. Several people pointed out you’re not just handing over your own history. You’re handing over years of things friends told you in confidence, without asking them first. That’s a fair point worth sitting with before you enable Full Disk Access.
This runs locally on your Mac rather than uploading your texts somewhere, which softens the privacy hit a little. It doesn’t erase the bigger question of consent for the people on the other end of those threads.
🏴☠️ Run the test, see what it tells you, and then go message the three people it names. The original poster also keeps a running doc of prompts exactly like this one. If this one landed, there’s a full list worth digging through.
Frequently Asked Questions
Q: Isn’t this a privacy issue since I’m sharing my friends’ conversations with an AI?
Valid concern. You’re handing an AI messages from people who never consented to being analyzed this way. Some people find the reflection valuable enough to accept the trade-off; others see it as crossing a line. Honest answer: both positions make sense. If you try it, maybe start with conversations you’ve already fully processed emotionally.
Q: I’m on Windows or iPhone, am I locked out?
Nope. You can copy and paste any conversation into ChatGPT and run the same reflection prompts. You just lose the ability to search your entire message history at once. But individual conversations work great.
Q: Should I actually send the messages ChatGPT drafts for me?
Not word-for-word. Use it as a draft, then rewrite it in your own voice. The AI version tends to feel generic. The real value isn’t the exact message, it’s that something nudged you to actually reach out. Make it sound like you.
Q: Won’t the AI miss what my relationships are actually like since it’s just looking at text?
Yeah, it will. A decade of friendship won’t fit in a chat transcript. Messages miss inside jokes, context, body language, and all the time spent together offline. Use the analysis as a starting point for reflection, not as the complete truth. Then layer in what you actually know from living it.
chatgpt can read your entire text history now. asked it who used to be in my daily life and quietly dropped out of it, and i wasn’t ready for the answer
by u/Professional-Rest138 in PromptEngineering