40 Relationship Improvement Questions

You'll Never Learn Until Your Ask

June 4, 2023 |

Growing Closer to Your Family

Looking for relationship improvement? Most people are, but many don’t know where to start. There is much you will never learn about those you’re closest to unless you ask. You’ll be surprised by what you discover from asking the relationship improvement questions below.

Start with the questions you’re most genuinely curious about. It’s fine if they want to pass or not answer. When interviewing family, consider making an audio or video recording of these interviews for future generations.

Questions 1 – 20

1. What was your life like in high school? Elementary school? Middle school?
2. How did you meet each other?
3. What did you want to be when you were growing up?
4. Who was your first girlfriend or boyfriend?
5. Tell me about your parents & grandparents.
6. Tell me about your cousins, aunts, and uncles.
7. What was one of your biggest challenges growing up?
8. Who did you feel the most unconditional love from growing up?
9. Have you ever almost died? What happened?
10. What are a couple of your biggest fears?
11. What do you think the greatest invention has been during your lifetime?
12. How would others describe you in middle school, high school, and/or college?
13. How much money does a person need to love life?
14. What is one of the best pieces of life advice you would give to someone younger than you?
15. What is something that was challenging in your childhood?
16. What are the 3 happiest times in your life?
17. How many times were you in love?
18. If you could have dinner with one person, dead or alive, who would it be?
19. Who is someone famous, dead or alive, you admire & why do you admire them?
20. Who was a positive role model in your life growing up, that was not related to you?

If you found this information helpful, SUBSCRIBE TODAY to receive my free video and workbook SHATTERPROOF YOURSELF: 7 Small Steps to a Giant Leap in Your Mental Health. 

Questions 21 – 40

21. Who was a positive role model growing up, other than your parents, who is related to you?
22. What would you have done differently as a teenager if you were 10 times more confident?
23. What would you have done differently in your career if you were 10 times more confident?
24. What would you do differently in your life NOW if you were 10 times more confident?
25. What’s a moment in American history that you will never forget?
26. Did you ever have a run-in with the law?
27. What was your first job?
28. What was your worst job?
29. What was your favorite job?
30. What is the craziest thing you have ever done?
31. What are your favorite memories of me while I was growing up?
32. What do you believe are some of my biggest talents?
33. Have you ever been really depressed? When and why?
34. What are some of your fondest memories from your childhood?
35. What is my birth story? What is my sibling’s birth story?
36. What was one of your favorite outfits as a kid or teenager?
37. What is one of the best things you’ve ever spent money on?
38. What is one of the worst things you’ve ever spent money on?
39. What is one of the best pieces of career advice you would give to someone younger?
40. Tell me about your first car. What happened to it?

Below is a PDF of all 40 of these questions. First, download it and save it on your desktop. Then, print off this tool and ask some of the questions, not just with family, but with anyone you’re close to. Share this list 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. My passion is to help people have healthy relationships. 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.

Questions Jar

“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 that knows and understands each other more. Additionally, use it with new employees during orientation as a way to start the creation of personal connections. My turnover has cut in half of my industry standard since using The Legacy Jar during orientation.” –Keith Sullivan from Amarillo, Texas

“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 Mitchell from Maize, Kansas

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