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.
Genuine, authentic, and heartfelt conversations connect people and transform relationships.
My parents and siblings are scattered across the country, so when we do manage to gather a few times a year, it’s special—but not always smooth sailing. We haven’t always seen eye to eye, so I’ll admit, I sometimes feel a little anxious walking into those first couple of meals together.
But here’s my go-to trick: I pull out one of the questions below and challenge everyone to answer it. There’s usually some eye-rolling or playful groaning at first, but I don’t give up. And without fail—every single time—something shifts. Laughter happens, stories get shared, and we all walk away feeling more connected and energized.
50 Fun Relationship-Building Questions
Questions 1 – 13
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 recently?
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?
13. What would you do differently if you knew nobody would judge you?
Questions 14 – 25
14. What are some of your most prized personal possessions?
15. What’s 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?
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Questions 26 – 37
26. What job did you want to have as an adult when you were a child?
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?
Questions 38 – 50
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?
Want to Spark Better Conversations? Start Here.
Let’s be honest—asking meaningful, relationship-building questions can feel a little awkward, especially if it’s not something you’re used to. You might worry people will resist or the vibe will get weird. That’s exactly why we created the 50 Relationship-Building Questions Activity—a simple, fun way to break the ice and get everyone connecting naturally.
Whether you’re gathered around the dinner table, leading a team meeting, or catching up with friends, this activity is designed to make great conversations easier—and a lot more fun.
What’s Inside:
You’ll get a printable set of 50 numbered questions plus 6 creative ways to use them, including:
- Mealtime Fun – Everyone picks a number and answers a question before and during the meal.
- Daring – Everyone answers the same question before moving on.
- Mindreading – Guess how someone will answer before they do.
- Chaos Mode – No rules! Jump in, ask questions, and keep it lively.
Just cut out the 50 numbered squares at the bottom of the PDF, toss them in a jar or cup, and you’re ready to go.
Download the activity now and turn small talk into real connection!
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