1. Given the choice of anyone in the world, whom would you want as a private dinner guest? What would you ask them or talk about with them?
2. Would you like to be famous? In what way? What benefits do you think you’d get from being famous? How would you use those benefits? What is your biggest concern or fear about being famous?
3. Imagine that your ten-year-old self were sitting beside you right now. That ten-year-old knows that you are them after they grow up…so they’re eager to get advice from you. What advice or suggestions would you give them about how they might make choices and live their life differently than the way you did?
4. What would constitute a “perfect” day for you? Describe it from beginning to end.
5. Imagine that you were suddenly given $100,000,000 with no strings attached. Would it change your everyday behavior and lifestyle? If so, how? Give details. How would you invest or give away or spend the money?
6. Imagine that you knew for sure that you would live with health and vitality until you were more than 251 years old. Would that change how you live today? If so, elaborate.
7. Which behaviors, more typical of the opposite sex than of your sex, are difficult for you to understand? Please explain. (Examples of more typical male behaviors: liking computer games/sports, refusing to talk when there is an upset, having/wanting more than one woman. Examples of more typical female behaviors: loving shopping, sharing her problems with her friends, being more moody.)
8. Name three things you and your partner appear to have in common. (back and forth)
9. What in your life do you feel most grateful for? (grateful to God, grateful to the universe, grateful to others unknown to you, grateful to others known to you, and grateful to yourself)
10. If you could change anything about the way you were raised, what would it be? How would you raise your child differently?
11. Take four minutes and tell your partner your life story in as much detail as possible.
12. If you could wake up tomorrow having gained any one quality or ability, what would it be? What would you do with it? What benefits would you get from having that ability?
13. What do you like about the opposite sex? What do you dislike about the opposite sex?
14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it already?
15. What accomplishment of your life are you most proud of? (proud of that you did for others and proud of that you did for yourself)
16. What do you value most in a friendship? What does friendship mean to you?
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? How and why?
20. Which advantages of being your sex (man or woman) do you like? Which disadvantages of being your sex would prefer to do without, if you could?
21. What do you like about your mother? What do you dislike about her?
22. What do you like about your father? What do you dislike about him?
23. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items each.
24. How close and warm is your family? Do you feel your childhood was happier than most other people’s, or not? In what ways?
25. Make three true “we” statements 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 with your partner, please share what would be important for him or her to know about you.
28. Imagine that you were living with another person. What might they discover about you (both positive and negative) that they probably would never learn if they weren’t living with you?
29. Share with your partner an embarrassing moment in your life…or share a secret about yourself that they don’t already know.
30. Each of us can be unaware of some of the ways that we are occurring for others. Ask your partner, “Just from your impressions of me, how do I occur for you (seem to you) that you think I might not know that you are thinking or feeling about me in this way?” For example, let’s imagine that you feel that I have not listened very well or deeply to you. And you suspect that I may not be very aware that you (and maybe others) experience me this way. Then this would be an example of something you might share with me, as in, “I don’t know whether or not this occurs with you and others, but, with me so far, it often didn’t seem as if you were listening to me very well.” Give your partner a 0-10 ranking on how well you have felt listened to by them. Then, if they are interested, gently give them some suggestions of how they might change their behavior so that you would feel better listened to.
31. If you are a woman, answer the question, “Specifically, how could a man treat me to make me feel safe, cherished, and adored?” If you are a man, answer the question, “Specifically, how could a woman treat me to make me feel powerful, respected, and admired?”
32. In what ways, if you had a life partner, would you want your relationship to be the same as that of your parents? And how would you want your relationship to be different from that of your parents?
33. Given that good listening does not necessarily mean obeying or agreeing, ask the other person the following questions, "Rank me 0-10 on how well you feel that I have been listening to you? Give me the reasons for your ranking. Also, whenever I have been the one speaking, rank me 0-10 on how sensitive you think I've been in noticing how you were listening to me as I spoke? Give me the reasons for your ranking."
34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save one other thing. What would it be? Why?
35. Of all the people in your family, whose death would you find most disturbing? How would it disturb you and why?
36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.
37. Comfortably and in silence, look into each other’s eyes, with an intention to create a soul-to-soul connection, for two-plus minutes (agree together beforehand if you want to try for more than two minutes). Afterwards, share with each other the thoughts and feelings that occurred for you while doing this.
Are you willing to have fun and explore the possibility of feeling more intimate with someone? If you search Google for “36 questions,” you’ll find a list of questions that will help you do this. I’ve used some of those questions, replacing many questions with my own (and adding in one more). You’ll find my “37 Questions” even more fun and effective.
Create a quiet, comfortable, and confidential setting to ask these questions back and forth with the another person. Maybe you know this person for only a short time or maybe for years. Prepare to be surprised by what you feel and discover. Answering these questions back and forth may take longer than one sitting. Don’t rush it. Enjoy!