125 How Well Do You Know Me Questions for Friends and Family

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You probably think that you know your close friends and family members very well… but do you?

The best way to find out is to play a little game of “20 Questions”… or in this case, 125 Questions!

We’ve put together a list of questions on a variety of topics. Depending on who you’re playing with, scan through and decide which ones are appropriate.

The ones you don’t know the answer to may surprise you!

So let’s get out a bottle of wine and some snacks and get to it. 

What Are How Well Do You Know Me Questions?

The goal of “how well do you know me” questions is to test someone else’s knowledge of that specific person. After the first question is asked, the person asking the question and the person answering the question can write down their answers. Then, they can show their answers at the same time, seeing if they are the same!

Even though you can use these questions to test another person’s knowledge of you, it is not supposed to define someone’s relationship. It is important to keep in mind that questions with incorrect answers (or unanswered questions) can also be used as starting points to get to know each other better. Furthermore, you can also use these questions to entertain each other with funny answer choices as well!

125 How Well Do You Know Me Questions

A few examples of fun “how well do you know me” questions include:

  1. Who is the person that I looked up to the most growing up? 
  2. What is my favorite food and how often do I eat that specific food? 
  3. Do I have any allergies to anything?
  4. If I were going to eat the same food every single day for a week? What would that be? 
  5. What is the one thing in the world that I am most afraid of? 
  6. What is the one goal that I have in life that I would like to accomplish more than anything else? 
  7. When the weekend rolls around, what is the one thing that I look forward to doing more than anything?
  8. When we went on vacation together as a family, what was my favorite destination? Where did I want to go more than anything else? 
  9. How old was I when I had my first romantic relationship with someone else? 
  10. Who is my favorite current celebrity? 
  11. Did I ever get in trouble with the police when I was growing up? What did I do? 
  12. When is my birthday? What do I usually like to do to celebrate? 
  13. What is my favorite clothing style? If the weather is appropriate outside, what do I always wear? 
  14. When I was in high school, what sports did I play? 
  15. Out of everything in the world, what makes me the happiest? 
  16. If I had a pet growing up, which one was my favorite? 
  17. Out of everything I do, what is my biggest talent? 
  18. If I had to choose, who would I like to go on vacation with the most?
  19. What is the longest relationship I have ever been in?
  20. What is the most annoying trait that I have? 
  21. What is the one thing that I will always put off if given the choice? 
  22. What is my favorite type of music? What is my favorite band? 
  23. What is the longest relationship that I have ever been in with someone else? 
  24. What is the best concert that I have ever been to in my life? 
  25. If I had my choice of alcoholic beverage, what would I get right now? 
  26. What do you think is the worst decision I’ve ever made in my life? 
  27. What is my middle name? 
  28. Out of all of my siblings, which one is my favorite? 
  29. Where was I born and where did I grow up? 
  30. How many times did I move before the age of 18? What house was my favorite? 
  31. Would you describe me as a religious person? If so, what type of practices do I follow? 
  32. What was my favorite class growing up? What was my least favorite? 
  33. Where did I go to college? Did I go to graduate school?
  34. Did I have to share my bedroom with a sibling growing up? If so, which one? 
  35. As a child, did I have the chicken pox? If so, how old was I when I had that? 
  36. Did I have a cell phone growing up? If so, how old was I the first time I got one?
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  1. How did my mother or father punish me as a child if I did something wrong? 
  2. What was my favorite TV show growing up? 
  3. Did I have a babysitter as a child? If so, did I get along with him or her? 
  4. How old was I the first time my parents let me stay home alone? 
  5. Have I ever been arrested? If so, what did I do? 
  6. Did I ever get suspended or expelled from school? If so, why? 
  7. How old was I the first time I had an alcoholic beverage? What was that beverage? 
  8. What was the very first job I had? How long did I have that job? 
  9. What was my favorite color growing up? 
  10. Out of every flavor of ice cream I ever tried, which one was my favorite? 
  11. If I were going to order a pizza, what toppings would I put on it? Do you think I would be able to finish the entire thing on my own? 
  12. If I were going to choose a superpower, what would my superpower be? Do you think I would use my powers for good or evil? 
  13. If I had my choice, what type of dessert would I order? Do you think I would eat that dessert every night if I could? 
  14. Would you say I was good at making friends as a child? Why do you think people liked me? 
  15. How old was I the first time I set foot on a plane? Where did I go? 
  16. If I were to get admitted to the hospital, what do you think would be the likely diagnosis? 
  17. What was the name of my high school? 
  18. What type of traditions did our family have growing up? 
  19. Have I ever spent time overseas? If so, where was my favorite destination? 
  20. Who was I named after? 
  21. What is the most fun I’ve ever had on New Year’s Eve? 
  22. How do you think I would react if I or my significant other got pregnant right now? 
  23. During high school and college, how many boyfriends and/or girlfriends did I have? 
  24. If given the opportunity, what could I talk about all day, every day? 
  25. Have I ever been around anyone in my life that I could not stand to spend time with again? 
  26. What is the most embarrassing thing I have ever done in public? 
  27. Did I ever have my heartbroken? If so, who was responsible for that? 
  28. Am I more of a dog person or a cat person? 
  29. Do I have any insecurities? If so, what are they? 
  30. Did I play a musical instrument growing up? 
  31. Who is my favorite sports team? 
  32. What is my zodiac sign? Do I believe in what my zodiac sign says about me? 
  33. If I got into trouble when I was younger, who did I call for help? 
  34. Growing up, who was my biggest celebrity crush? Who did I always dream about spending time with? 
  35. Growing up, who was my best friend? Who did I want to spend the most time with? 
  36. Who was my very first girlfriend or boyfriend? How long did that relationship last and why did it end? 
  37. Out of all of my family members, who do I spend the most time with? Who do I like the most? 
  38. When I was a child, did I have a favorite toy? What was that toy and do I still have it? 
  39. When I wake up in the morning, what is the first thing I usually do? Is there anything specific that I have to do immediately? 
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  1. How old was I when I had my first kiss?
  2. How old was I when I had my ears pierced?
  3. Do I have any tattoos? How many?
  4. Did you ever think about getting a tattoo? What would you get?
  5. Did I ever have an imaginary friend as a child?
  6. Do I believe in ghosts?
  7. Do I believe in Heaven and Hell? How about purgatory?
  8. Do I want to be buried or cremated when I die? 
  9. If I could go back in time, which age or moment would I choose to revisit?
  10. If I could spend a week in the future, how far ahead would I jump?
  11. If I could find out how and when I will die, would I want to know?
  12. Have I ever had a pregnancy scare?
  13. Do I believe in abortion?
  14. What is my biggest regret from a failed relationship?
  15. Have I ever been engaged and broke it off?
  16. Have I ever ridden a horse?
  17. Have I ever ridden a motorcycle? Was I on the back or was I driving?
  18. Have I ever been skydiving?
  19. If I could bring one loved one back to life for one day, who would I choose?
  20. Did I ever visit a psychic?
  21. Did I ever cheat on a partner?
  22. What am I most self conscious about?
  23. Is there any animal that I am afraid of?
  24. If I could be on any game show, which would I choose?
  25. If I could step into any band as lead singer, which band would I choose?
  26. Have I ever been in a fight?
  27. How old was I when I lost my virginity?
  28. Have I ever drank so much I blacked out?
  29. Would you rather have me as your pictionary or trivial pursuit partner?
  30. Have I ever gone streaking or skinny dipping?
  31. Have I ever had sex in a public place? Where?
  32. Did I ever shoplift?
  33. Have I ever ridden in the back of a police car?
  34. Have I ever sang karaoke?
  35. What is my dream vacation destination?
  36. Do I want kids? How many would I like to have?
  37. What was my worst subject in school? How about my best?
  38. Who is my favorite teacher or professor of all time?
  39. Did I play an instrument growing up?
  40. What was I most scared of as a kid?
  41. Was I close with my grandparents growing up?
  42. Did I have a favorite Aunt and Uncle? Who were they?
  43. What was my high school experience like?
  44. Did I play any sports growing up? Which ones?
  45. When did I stop believing in Santa Claus?
  46. Was I closer with my mom or my dad when growing up?
  47. Did I ever catch my parents having sex?
  48. How old was I when I attended my first funeral? Who was it for?
  49. What was my first job?
  50. What was my first car?

Final Thoughts on How Well Do You Know Me Questions

I hope you found these questions both fun and enlightening. After all, we didn’t want to get too heavy on you.

But there are plenty of topics and questions out there, designed to help people get to know each other better.  And some can actually be serious if that is what you’re looking for. 

For instance, if you’re in a committed relationship, you may want to check out this article on thought provoking questions for couples.

Planning a road trip anytime soon? Check out this list to help pass the time.

Or perhaps you’re looking to spend some quality time getting to know your kids better?  This article offers some clean and fun “would you rather questions” for them to answer.

At the end of the day, you’ll never get the answers you seek in life if you’re afraid to ask questions.  

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125 How Well Do You Know Me Questions for Friends and Family

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