What is your most embarrassing moment with me?
Follow-ups: Do you still think about it? • What did you learn?
What is your favorite memory of our friendship?
Follow-ups: Why does it stand out? • Do you want to recreate it?
What is something I do that annoys you?
Follow-ups: Should I change it? • How long has it bothered you?
What is your favorite thing about our friendship?
Follow-ups: How did we develop it? • What makes us work?
What is something you wish we did more often?
Follow-ups: Why is it important? • When can we do it?
What is your funniest story about us?
Follow-ups: Do others know about it? • Should we tell more people?
What is something I have helped you with?
Follow-ups: How did it help? • What did it mean to you?
What is a secret we share?
Follow-ups: Should we keep it forever? • Who else knows?
What is something you have always wanted to tell me?
Follow-ups: Why have you not said it? • How do you feel now?
What adventure should we go on together?
Follow-ups: When should we go? • What should we do there?
When did you first realize we would be good friends?
Follow-ups: What made you think that? • Were you right?
What is something you admire about me?
Follow-ups: Have you always felt that way? • Has it influenced you?
What is your favorite inside joke we have?
Follow-ups: How did it start? • Should we explain it to others?
What is a challenge you think we should do together?
Follow-ups: Why that one? • When should we start?
If we could switch lives for a day, what would you do?
Follow-ups: What would you want to experience? • What would surprise you?
What is something you have never told anyone else?
Follow-ups: Why me? • How long have you held onto it?
What is a tradition you want us to start?
Follow-ups: Why that one? • When should we begin?
What do you think is unique about our friendship?
Follow-ups: How did we develop that? • Do you have it with others?