Asking questions is a form art. Here are I collect my fav ones.
My questions
What most surprised you in X?
What solution, definition you are anxious to bring to the world?
But this could also be a lot broader. What is under-valued or under-discussed? What problems your mind goes to automatically to explore. What overlapping concepts or intersections of disciplines you think often about? What should we start thinking more about or what should we start doing more of?
How our society should tackle
How our society should counter-act our
If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
“what is your relationship with X? What is your relationship with fitness? With food? With the internet? “What is the history of your relationship with music? With travel? With leadership? With taking responsibility? Strength? Vulnerability? Fashion? Self-expression? Optimism? Being a public figure? Privacy? Intimacy?” via 
What skills should be thought at schools?
Who are the five people that influenced you the most?
What are the most important neglected projects humanity needs to work on?
What are your the most fascinating books, documentaries, lectures?
If you had a trillion dollars what projects what would you engage in?
What is your intuition how much “western” scientific understanding covered all areas of knowledge (perhaps intuitive answer from 0 to 100). Where are the most likely blindspots of "Western" understanding of the world?
What did you recently change your mind on?
Askhole
From askhole.io
Have you ever had (what you consider to be) a spiritual experience? If so, what was it like and what effects did it have on you?
Have you been loved enough?
If you could have one but not the other, would you rather love someone or be loved by someone?
Which life lessons that you’ve learned would be most important for the people in this room to hear?
Of all the beliefs you hold, which is most likely to be considered barbaric in 150 years?
If you could press a button that would instantly erase every single false belief you have, would you do it?
What unusual trait do you find most attractive in a romantic partner?
In what ways do you tend to fail at communication?
Who in the room do you admire the most?
Are there any thoughts so offensive that you would advocate shaming those who think them, even if they don’t act on those thoughts?
Are you more concerned with improving the world or improving yourself?
Do you have more thoughts or more feelings?
Do you feel that you have conscious control over your beliefs? Could you, right now, decide to believe something else if you tried? If so, which beliefs?
What do you still owe someone an apology for?
Would you support the use of realistic child sex dolls for pedophiles?
Rose questions
Good when catching up with a friend. Imagine a rose – what is a petal? (best part), thorn? (worst part), bud? (growth). I extrapolated to:
What surprised you? What was a moment of joy? What broke your heart? How did you grow?
The 36 Questions to connect
(The original title of the set is The 36 Questions That Lead to Love. I don’t like the title because it seems like we ask these questions with a hidden agenda. Because of the title it seems like this is a tool for persuation. But these are good questions to get to know each other, not only in romantic only setting. Perhaps should be renamed to 36 Questions for Connection Connection.
Set I
1. Given the choice of anyone in the world, whom would you want 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 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 you and your partner appear to 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 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?
Set II
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 that 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 your partner. Share a total of five items.
23. How close and warm is 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?
Set III
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.
28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
29. Share with your partner an embarrassing moment in your life.
30. When did you last cry in front of another person? By yourself?
31. Tell your partner something that you like about them already.
32. What, if anything, is too serious to be joked about?
33. If you were to die this evening with no 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 safely make a final dash to save any 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 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.
Other question pages
In the spirit of the classic 36 Questions to Fall In Love, here are some high variance, negative expectation value questions to answer with your loved one.
- If you could change one thing about your partner's personality, what would it be?
- If you could change one thing about your partner's appearance, what would it be?
- What's the worst thing you've ever said about your partner behind their back?
- If you imagine having children with your partner, what's the biggest concern you have about their genetics?
- What person that you know does your partner most seem like a worse version of?
- If your partner was dating someone else and that person broke up with them, what would you guess was the reason why?
- If you could choose how much your partner loved you, would you choose to have them love you less or more? How much?
- Would you increase or decrease their sex drive?
- If you could change one thing about your partner's sexual preferences, what would it be?
- How much younger or older could your partner be before ynou were no longer willing to date them?
- Imagine your partner could change to be much more like the kind of person they wanted to be. Are there ways in which you think they would become worse from doing this?
- To what extent does your partner's success make your relationship better or worse?
- To what extent do you think you and your partner mislead yourselves about each other in order to enjoy your relationship more?
- What true statement has the maximum probability of causing you to break up right now?
- If you could cause your partner to magically move in the direction of having some of the strengths of any other current or former lover of yours, which lover would you choose?
- What delusions about your partner would be most helpful for you enjoying dating them more?
- Since you started dating, when did you feel most embarrassed of your partner?
- Since you started dating, when did you feel most unattracted to your partner?
- What about your partner's interest in you do you think is most unattractive or embarrassing?
- How big is the intelligence difference between you and your partner?
- How big is the difference in your expected positive impact on the world?
- Who would you be most embarrassed to introduce your partner to?
- What feature of your partner is your partner most unreasonably proud of?