50 Fun Relationship-Building Questions

Great Conversations Start with Great Questions

Young couple in cafe

Genuine, authentic, and heartfelt conversations connect people and transform relationships.

Here’s a list of 50 of my favorite relationship-building questions. They’re light and fun, get you to think, and come from over 25 years of helping people open up in my work as a family therapist.

Questions 1 – 25

1. What is your favorite time of the day? Why?
2. What cheers you up?
3. What are some of your goals for the next year?
4. If you could rid yourself of one bad habit, what would it be?
5. If you had fewer inhibitions, how would you behave differently?
6. What are some positive things that have happened in your life over the last week?
7. Life is too short to tolerate ____________.
8. Tell us about a habit you are proud of breaking.
9. How has fear impacted you
10. What are some of your favorite desserts?
11. What is one of your favorite questions to ask a stranger to start a conversation?
12. What is something abnormal or daring you’ve eaten? When and where?
13. What would you do differently if you knew nobody would judge you?
14. What are some of your most prized personal possessions?
15. What is something you have never done but want to do before your life ends?
16. What would I be surprised to learn about you?
17. What is something you have done or made that you are proud of?
18. What are your favorite things to spend money on and why?
19. How did you first meet one of your best friends? What are they up to now?
20. What is one of your favorite quotes?
21. What are some of your lifetime goals?
22. What is one of your favorite holiday memories?
23. What food dish would you like to become great at making?
24. Have you ever had a nickname? What is it and who gave it to you?
25. What is something that you regret buying?

If you found this information helpful, SUBSCRIBE TODAY to access my free video & worksheet, Shatterproof Yourself: 7 Small Steps to a Giant Leap in Your Mental Health.

Questions 26 – 50

26. What job did you want to have as an adult when you were a child or teenager?
27. What other careers or jobs interest you outside your current career?
28. What is one of the best gifts you have ever received?
29. What was your first job, how did you get it, and how did it turn out for you?
30. What teachers have impacted your life? Explain your answer.
31. What is one of the nicest hotels you have stayed in? What made it nice?
32. What do you wish you were great at?
33. What is your ideal evening?
34. When have you exceeded your own expectations? What did you do?
35. Other than money, what have you gained from work?
36. So far, what have you enjoyed about today?
37. What did you enjoy yesterday?
38. Of all living people, who would you most like to have dinner with?
39. What are some of your favorite movies?
40. Who are some of your favorite comedians? Why do you find them funny?
41. Who is a friend of yours who makes you laugh? How do they do it?
42. What are your favorite card games and why do you like them?
43. What are some of your favorite kinds of candy? Why?
44. What are your favorite drinks? Why?
45. How would your parents describe you?
46. What were some of your favorite books as a child? Why?
47. What is your motto for life?
48. Are you a spender or a saver? Explain.
49. What is one of your favorite songs? Why?
50. What are some of your favorite compliments to receive?

If you found this information helpful, SUBSCRIBE TODAY to access my Free video & worksheet, Shatterproof Yourself: 7 Small Steps to a Giant Leap in Your Mental Health.

Below is a PDF of all 50 of these questions. Download it and use it as a tool to connect with your work co-workers, family, and friends. It works great for team meetings and family events (e.g. Thanksgiving). Share it with your friends, family, and co-workers.

If you like these questions, you’ll LOVE The Legacy Jar. Check it out below. Most people are hungry for connection. I developed the Legacy Jar as a way to inspire meaningful conversations. Your Legacy Jar includes 108 different questions on a variety of topics. Pick a question and answer it. It’s that simple and some serious fun as well.

“I highly recommend The Legacy Jar. I’ve used it many times at work, at home, and at church events. The questions are excellent. My 5th graders used to beg me at school to play it. I’ve purchased dozens for my family and friends.” – Heidi from Maize, Kansas

“I use The Legacy Jar with 2 parts of my business. I use it weekly with my management team. It has allowed us to become a tighter team and understands each other more. I also use it with new employees during orientation as a way to start the creation of personal connection. My turnover has cut to half of my industry standard since using The Legacy Jar during orientation.”Keith from Amarillo, Texas

“I’ve used the legacy jar with an eighth-grade Sunday school class, students in 4th grade, and an adult group, and everyone loved it! I find it amazing that this tool works for families, couples, in the classroom, team building, etc. I’m a fan!” – Tiffany from Metairie, Louisiana

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