20 Great Questions to Develop a Deeper Understanding

Asking questions is a great way to gain a deeper understanding of a person. If you’ve known them for a long time or are just meeting them, it is always the perfect time to get to know someone better. Here are 20 questions to get you started, explain your answers and let the conversation flow naturally. Feel free to post your own in the comments below!

1. Are you a morning or an evening person?
2. Do you have a favorite thing that you do every day?
3. If you could do anything, what would you do?
4. What do you like to eat and drink?
5. When do you feel the most creative?
6. Out of all the places you’ve visited and lived, which one is your favorite and why?
7. What is one of your favorite actives? Should we go do this now?
8. What do you wish you could do better?
9. What do you miss about the past?
10. What are you excellent at?
11. What do you wish you could do better?
12. What did want to be when you grew up?
13. If you were writing an autobiography, what would the chapters be?
14. What is one project you’ve put on the back burner that you wish you could finish?
15. What are some of your personal rules you live by?
16. If you had one million dollars to give away, what would you do with it?
17. What do you want to be remembered for?
18. If you could acquire one skill set with no effort, what would it be and why?
19. If you could have everyone in the world do one thing for a day, what would you have them do?
20. What are three things you always wish you’d done?