Feature Request: Allow ChatGPT to Message Users First

ChatGPT Feature requests
1

I think it would be really nice if ChatGPT had an optional feature that allows it to message the user first.

Right now, conversations are mostly one-sided—you open ChatGPT and send the first message. Scheduled Tasks are already a great step toward proactive communication, but I think this could go one step further.

For example, users could turn on a setting like:

“Allow ChatGPT to message me first”

If enabled, ChatGPT could occasionally send things like:

- A simple good morning message

- A reminder about something we previously discussed

- A follow-up like “How did that thing go?”

- Something interesting related to a previous conversation

- Or just a casual check-in from time to time

Of course, this should be completely optional. Some people wouldn’t want ChatGPT sending them messages, while others would really enjoy it. Users could choose whether to enable it, how frequently ChatGPT can message them, and what kinds of messages are allowed.

I think this would make ChatGPT feel much more like an ongoing conversation rather than something you only interact with when you open the app.

Scheduled Tasks are already close to this idea, but allowing ChatGPT to occasionally initiate a conversation on its own would be a really interesting next step.

I’d love to see this considered as an opt-in feature! :raising_hands:

2

I’d like to share a small experiment that builds on this suggestion using ChatGPT Tasks / condition monitoring.

I prototyped a workflow I call “Context Nudge”: a recurring task evaluates the context available to it and decides what might be useful to say, whether to send a notification at that check, or whether to remain silent. The checks run on a schedule; the specific message and the decision to notify are left to the AI rather than specified as individual reminders.

One useful example: it connected a YouTube meeting the following morning with recent high-performing social posts we had discussed. It proactively suggested sharing two or three successful examples with the team before the meeting. I had not explicitly set a reminder to do that, and the suggestion prompted me to act.

This is a small anecdotal result, but it made the potential of context-aware proactive messages tangible for me. The value was in connecting relevant context and identifying a useful next step at an appropriate moment.

I’m sharing this as product feedback on a possible extension of existing Tasks capabilities. An opt-in experience with frequency limits, quiet hours, and an explicit option to say nothing would make this especially useful.