Trying to create a multifunctional assistant

Hey, I’m trying to make a language instructor. More like a coach since will be used not for learning but for reviewing. Tried making an assistant out of it, seems like the easiest approach to practice prompt engineering and such.

I have a list of topics that I want the assistant to focus on (list is way longer)

  • What should you do if you have the flu?
  • What should you do to be healthier?
  • Who is the best person you have ever met and why?
  • Requests with can and could
  • Compare characters (ex Elsa vs Aladdin)

The issues I’ve faced is that giving the assistant the entire list just makes the assistant go through the topics one by one, crossing them out of the list. I wanted the assistant to have a conversation and practice these as they came up. Plan b was to send the topic as the first message, however, this sometimes got ignored, and the conversation quickly came to an end.