40 Thought-Provoking Questions to Get to Know Your Family


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Think you know everything about your family members? Chances are, you probably don’t. 

Jump ahead to these sections:

What if you were to ask more family questions? Just think about what you could uncover. You could learn the ways family members remember past events. You could get a new appreciation for family stories from their point of view. You could even discover things about their lives you never knew.

Funny questions like "What's the craziest thing you've ever done?" or informative ones such as "What did you find rewarding and challenging about being a parent?" are great family questions to get the conversation going.

Funny Questions to Ask Family Members

List of funny questions to ask family members

Having a family reunion? Looking for a new twist on family game night? Asking your family members funny questions can be a great ice breaker or a fun way to pass the time. We’ve pulled together a list of fun questions to help you get to know your family members better.

1. “When you were a teenager, what got you into trouble?”

You may view your parents and grandparents as only disciplinarians or authority figures. Find out about their hidden rebellious sides.

2. “Did you ever play pranks on your siblings?”

Siblings may seem like they’ve been put on this planet just to drive you crazy. Ask about sibling rivalry from prior generations. 

3. “Did you ever have a run-in with the law?” 

Your parents and grandparents try to teach you right from wrong but they might not always have been on the right side of the law!

4. “What’s the craziest thing you’ve ever done?”

Not all parents share the adventures of their misspent youth freely. These stories can make for fun and wild stories once you’ve grown up. 

5. “What was the worst job you ever had?”

We’ve all had to work terrible jobs. You might be surprised to learn about your dad’s chicken farming days. 

6. “Do you have any hidden talents?”

People usually like to talk about things they’re good at. But some talents might be under your radar.

7. “Did you ever hide things from your own parents?”

You can learn a lot about your parents or grandparents by finding out what they wanted to hide. 

8. “What’s the silliest thing you’ve ever done?”

You might not be able to imagine your parents or grandparents being goofy. This can let you know about a whole new side of them. 

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‘How Well Do You Know Me?’ Family Questions

Example of a question to ask your family to see how well they know you

How well does your own family know you? These questions can help your family members gain some better insight into who you are.

9. “What’s a major event you remember from my childhood?”

We all have events that have made a huge impact on us. You can see how well your family remembers the formative events that made their mark on you.

10. “What was my favorite book when I was little?”

Your parents may do things before you can formulate concrete memories. This might include reading to you every night. Asking your parents might help tap into new memories of your own. 

11. “What did I want to be when I grew up?”

When you’re a kid, it seems like everyone asks you about your future plans. See how closely your parents paid attention to your aspirations.

12. “When I was a teenager, what is the thing I did that upset you the most?”

Teenagers excel at pushing boundaries. See how your parents’ memories of your teenage years stack up against your own.

13. “What are your first memories of me?”

Parents actually remember things about your life that you don’t. This question can illuminate a lot about your parents’ earliest memories of you. 

14. “Who was my first crush?” 

You don’t always let your parents in on your inner lives when you’re young. See if your parents were paying attention anyway.  

15. “What do you think is my biggest talent?”

You don’t always see yourself the way others view you. Here, you can find out about how others perceive your strengths. 

16. “What do you think is my favorite book/TV show/movie?”

See how well your family understands where your interests lie.

Questions to Ask About Family History and Stories

List of questions to ask about family history

Your parents and grandparents have access to so many memories you’ve never heard. Check out these questions to ask older people and reach out to your family members. You may be surprised by what you find out. 

17. “Of all the things your parents taught you, what do you think helped you the most?”

Asking this question can help you learn about the priorities in multiple generations of your family. It can also give you insight into what shaped your parents growing up. 

18. “Do we have any famous or infamous people in our family tree?”  

Odds are you would have heard about famous relatives if they were notable for something good. Your parents and relatives might have avoided talking about someone more nefarious. Now is a good time to learn some unsavory family history.

19. “How did Grandma and Grandpa meet?”

You may know how your parents met. Grandparents may be a bit more of a mystery. 

20. “What is your favorite memory of your parents or grandparents?”

Grandparents and parents were once kids, too. Learning more about their childhood can help you connect.

21. “What family member were you closest to growing up?”

Sometimes the best way to get to know someone is by learning about that person’s relationships.

22. “How did some of our family traditions originate?”

You may have rituals you engage in without even realizing it. Maybe every year for Christmas your grandma makes a special cake. Ask for the stories behind those particular traditions in order to understand them better. 

23. “What family traditions have we let lapse that you’d like to bring back?”

Certain things may fall to the wayside as you grow older. See if certain childhood traditions can be revived for grandchildren.

24. “What family members do you wish I would have gotten to know?”

Sometimes grandparents or great-aunts pass away when you’re young. See if your family is ready to open up about those you’ve lost.

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Great Questions to Ask Around the Family Dinner Table

Example of a question to ask around the family dinner table

Add a fun element to a family meal — ask some questions around the dinner table.   

25. “What did you find most rewarding and most challenging about being a parent?”

As you grow older, you develop more of an appreciation for what your parents dealt with to raise you. Find out more about their thoughts from that time.

26. “Were there things you swore you would never do as a parent that you actually ended up doing?”

They say the most confident parents are the ones who don’t have children yet. Learn how your own parents adjusted their expectations.  

27. “How did you balance work and family life when I was a kid?”

It’s a struggle to maintain boundaries. Find out how your parents handled that challenge. 

28. “What family traditions have we let lapse that you’d like to bring back?”

Yes, this is the same question for earlier, but it’s a great question in this context!

29. “What do you think is the secret to a long and happy relationship?”

Have your parents or grandparents been together for many years? Discover the secret to their success. 

30. “What do you think our family motto should be?”

Some families have a code that they live by. It can be a fun exercise to put that into words. 

31. “What was your first car?”

Cars from older generations seem much cooler than what’s on the road today. Find out what your parents or grandparents rode around in during their youth.

32. “Who has had the biggest influence in your life?”

You can learn so much about the people who inspire you by discovering who inspired them.

Other Great Questions to Ask Your Family

List of other great questions to ask your family

So far, we’ve given you some questions to ask your family under particular circumstances. But there are questions that are good for any occasion. Whether you’re constructing a family tree or looking to pass time on a road trip, these questions are sure to be entertaining and informative. 

33. “What do you know now that you wish you had learned earlier in life?”

Sure, you need to learn some things yourself in your own time. But it’s undeniable that your life would have been easier had you figured some of these things out sooner. 

34. “What did you want to be when you grow up?”

You have dreams when you’re young. Hearing about other people’s early dreams can give insight into who they are.  

35. “What’s the biggest challenge in your life that you had to overcome?”

Adversity can really shape people. Find out what obstacles your family members have had to tackle in their lives. 

36. “What’s a piece of advice that you wish you had taken?”

It’s easy to hear good advice, then never take it. Examining the whys can be illuminating for everyone. 

37. “Do you have any advice on getting through personal struggles?”

Finding out how people pushed past their hardships can be inspirational. 

38. “Can you tell me about your first love?”

Your parents may not have always been together. They likely dated other people first. See what you can discover about those relationships. 

39. “What was your wedding like?”

Find out how your parents began their love story.  

40. “Who is the best friend you’ve ever had?”

You can learn a lot about a person by the company he or she keeps. 

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Get to Know Your Family Better with These Informative and Entertaining Questions

When you’ve spent your whole life with your family, it’s easy to feel like you know everything about them. But people have long memories and rich inner lives. There are many things you’ll never learn about them unless you ask. These questions can help reveal untold surprises about the people you love. 

Post-planning tip: If you are the executor of a deceased loved one's estate and you didn't get a chance to ask the important questions, we have a post-loss checklist that will help you ensure that your loved one's family, estate, and other affairs are taken care of.

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