1. Given the choice of anyone in the world who would you want to have as a dinner guest?
2. Would you like to be famous? In what way?
3. Before making a telephone call do you ever rehearse what you are going to say? Why?
4. What would constitute a “perfect” day for you
5. When did you last sing to yourself? To someone else?
6. If you were able to live to the age of 90 and retain either the mind or the body of a 30-year-old for the last 60 years of your life, which would you want?
7. Do you have a secret hunch about how you will die?
8. Name three things the two of you have in common.
9. For what in your life do you feel most grateful?
10. If you could change anything about the way you were raised what would it be?
11. Take four minutes and tell your life story in as much detail as possible.
12. If you could wake up tomorrow having gained one quality or ability what would it be?
13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
14. Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
15. What is the greatest accomplishment of your life?
16. What do you value most in a friendship?
17. What is your most treasured memory?
18. What is your most terrible memory?
19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
20. What does friendship mean to you?
21. What roles do love and affection play in your life?
22. Alternate sharing something you consider a positive characteristic of the person you’re with. Share a total of five items each.
23. How close and warm was your family? Do you feel your childhood was happier than most other people’s?
24. How do you feel about your relationship with your mother?
25. Make 3 true “we” statements for each. For instance, “We are both in this room feeling …”
26. Complete this sentence, “I wish I had someone with whom I could share ….”
27. If you were going to become a close friend of the person you’re with, share what would be important for her or him to know.
28. Tell the person you’re with what you like about them; being very honest and saying things that you might not say to someone you just met.
29. Share an embarrassing moment in your life.
30. When did you last cry in front of another person? By yourself?
31. Tell the person you’re with something you already like about them.
32. What, if anything, is too serious to be joked about?
33. If you die this evening without the opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
34. Your house containing everything you own catches fire. After saving your loved ones and pets you have time to make one final dash to save one item. What would it be? Why?
35. Of all the people in your family, whose death would you find most disturbing? Why?
36. Share a personal problem and ask for advice on how the person you’re with would handle it. Also, ask the person you’re with to reflect back to you how you seem to be feeling about the problem you have chosen.

Watched one of these videos by Jubilee where two strangers ask some of the questions above.

I'm going to try these questions with my best friend. We've known each other close to 8 years now and I'm curious to hear his answers for these questions.