Sometimes I am not the best at conversation. But asking a question is usually a good way to keep a conversation going.
Questions such as:
- How are you, really?
- How is your family doing?
- How is your job/business/etc.?
- I am thinking of taking up a new hobby. What do you like to do?
- Do you have any new projects going on?
- Can you recommend a book/movie/recipe?
- I need advice about ______. Do you have an ideas?
- Do you understand _______ that I’m having a hard time with?
- What do you hope for?
- What are you struggling with?
- Where did you grow up?
- Where have you lived? What has been your favorite place to live?
- What is something you miss in your life? What is something you are grateful for?
And ask someone a question that you wished someone would ask you.
But listening and caring about the answers might be even more important than asking the initial question. Listen enough to ask a follow-up question about what they are saying.