You may consider making a list and have them answer the ones they are able to answer. It is interesting also, maybe, the questions they can’t or don‘t want to answer. 😀 I pulled a list off the net and modified all of the questions; dropped a few and added some. What do you see yourself doing with your life in 5 years, 10 years? Have you had an experience you would say has impacted the direction of your life? Have you had to make an important decision that affected the direction of your life? Your best friend also wants to share everything but just waiting for you to ask something exciting, funny and important.
Asking questions work amazingly to improve relationships between two friends.
A conversation gets boring if you don’t have interesting questions to ask.
Will you be OK with me hanging out with you and your friends? If you could change something about your life, what would it be?
Do you think it is important to learn any form of a performing art?
Do you regret any of those intimate experiences with that person? Have you ever had the feeling you were being watched, in general, not during, you know.