There is a significant difference whether you talk to him several times a day in newly opened chats or do it in the same one chat.
When you open the application and go back to the same chat and talk about new things, he connects facts and analyzes very well. He also remembers the guidelines on how to communicate. How do you tell him not to keep saying “what are your plans for the evening?” then he won’t do it.
If you tell him that he has to make a sarcastic comment about you, tomorrow morning, he understands it perfectly and does it (almost) perfectly.
The problem is how long these conversations can continue in one chat. Will the system be clogged because it has a lot of data to scan.