225 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, 225 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!

Finally, if you want a handy version of this article, we've included a downloadable and printable version of these questions at the end of this article.

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!

So let's dive into the specific questions people can ask to know you better.

225 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?

[Feeling Lonely? See these ‘no friends' quotes to show that you are not alone]

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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?
  51. What was my favorite color when I was in high school?
  52. Can you name my favorite hobby, and how often do I participate in it?
  53. What's my favorite song to sing along to when it comes on the radio?
  54. Do you know how I broke my arm when I was a kid?
  55. What do I like best about the Fall season, besides Pumpkin Spice everything?
  56. When I'm stressed out, what's my go-to comfort food?
  57. Can you recall when I was the most scared I've ever been in my life?
  58. Which celebrity do I gush over at the movies, and what was the last movie I saw them in?
  59. If I could go anywhere in the world, what would be my dream travel destination?
  60. Do you know what I like best, traveling by airplane or traveling by train?
  61. Who is my favorite author and what was the last book I read from that author?
  62. Can you guess how many books I've read over the course of my lifetime?
  63. What's my shoe size now?
  64. What city did I live in when I was in second grade?
  65. Do you remember my high school's mascot?
  66. Can you name my closest childhood friend?
  67. Have I ever betrayed a friend?
  68. If I could have any profession in the world, what would be my dream job?
  69. Can you name my favorite TV show from the 1970s?
  70. What's something that someone does that really gets my goat?
  71. Do you remember my second job?
  72. What's my favorite way to spend a rainy day, and would you like to spend one with me?
  73. Do you know how I like my coffee, iced or hot, with sugar, and/or cream, and would I buy it from a coffee shop or make it at home?
  74. What's my mother's middle name?
  75. Do you know my favorite holiday and how I celebrate it?
  76. What's my most treasured possession, and who will I leave it to in my will?
  77. How did I wear my hair when we first met?
  78. What President did I vote for the first time I voted?
  79. What's my favorite ice cream flavor of all time?
  80. Can you name my favorite sport to watch on television, and can you name my favorite sports team?
  81. What's my superpower?
  82. Do you know my favorite kind of chocolate dessert?
  83. What do I like to do best in the great outdoors?
  84. Do I have a lucky number, and do I use it when I play the lottery?
  85. With all the apps on my phone, can you guess which my favorite is?
  86. What's my favorite animal to have as a pet?
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  1. What's my favorite wild animal, and have I ever written a poem about it?
  2. Can you guess my favorite type of flower, and do I have it in my house or yard?
  3. When I'm choosing a book or movie, do you know my favorite historical period to read about or watch?
  4. What's my favorite type of art to create?
  5. Can you guess my favorite museum to visit?
  6. What's my favorite hot beverage and cold beverage?
  7. Do you remember the last time we played a video game? Which one, and who won?
  8. Do I like pineapple on my pizza?
  9. Can you name my favorite type of candy, and would I rather get it on Valentine's Day or Halloween?
  10. On the weekend, what's my favorite way to spend a lazy Sunday?
  11. Do you know whether I love or hate thunderstorms?
  12. What is the one thing in the world that I would never choose to eat even if I was starving?
  13. In thinking about breakfast foods, if you took me out, would I order pancakes, grits, or oatmeal?
  14. If we visited Italy, where would I want to go sightseeing first? 
  15. Do you know what my best subject in school was?
  16. When I'm putting together a sandwich, would I choose peanut butter or bologna as my favorite ingredient?
  17. If I said I was coming to pick you up in my favorite car, what kind of car would it be?
  18. If you brought me a box of my favorite cookies, what kind of cookies would be in the box?
  19. Do you know my favorite scent?
  20. When I order cheese on a hamburger, what kind of cheese do I prefer?
  21. What's my favorite, iced tea or hot tea?
  22. When I'm grocery shopping, what kind of cereal do I pick from the cereal aisle?
  23. Do you know my favorite color of lipstick? Do I match it with my nail polish color?
  24. What's my favorite type of fruit juice?
  25. Do I prefer pecans, walnuts, peanuts, or mixed nuts?
  26. When I take a sick day from work, do you know what I'm doing?
  27. Do you know my favorite flavor of potato chips?
  28. What's my favorite flavor of flavored water?
  29. When I'm having a hotdog, do I prefer ketchup, mustard, or both?
  30. When I order seafood at a restaurant, what's my favorite dish? A bonus point if you know what sides I order with it?
  31. When I have a salad, what's my favorite type of salad dressing?
  32. Do I like grilled cheese sandwiches with or without mayo? With or without soup?
  33. When I need a little pick-me-up, what's my go-to energy drink?
  34. Can you name my favorite fast-food restaurant?
  35. If I ask you to bring me my favorite kind of cake on my birthday, what kind of cake are you bringing?
  36. Do I prefer lemon pie or key lime pie?
  37. If I was going to eat sushi, what kind would it be?
  38. Do I like savory or sweet BBQ best, and have I ever been to a Pig Pickin'?
  39. Who's my favorite motivational speaker, and have I ever seen them speak in person?
  40. Which self-help book have I read more than three times?
  41. What's my favorite food at Mexican restaurants, and do I order it every time I visit or just occasionally?
  42. Can you name my favorite type of spicy Indian dish?
  43. How many languages can I speak fluently?
  44. Do I know American Sign Language?
  45. When I go to a Greek restaurant, what do I usually order?
  46. The last time I was pregnant, what food did I crave?
  47. What was the name of my first pet and what breed was it?
  48. Do you know the story behind my pet's name?
  49. Did I ever get in trouble in middle school, and how much trouble did I get in when my parents found out? Or did they find out?
  50. Can you tell me what year I was born?
  51. What's my favorite type of European dish and when was the last time I had it?
  52. Do you know my favorite type of South American dish?
  53. What is the best way to put a smile on my face?
  54. If we were to travel to Australia, what would I want to do first?
  55. What's my favorite thing to do on a Caribbean cruise?
  56. Do I prefer the hot weather in the middle of Summer or cold weather in the middle of Winter?
  57. How old was I when the Tooth Fairy visited me for the first time?
  58. Do I have any aspirations for running for a political office?
  59. What is my favorite romantic comedy to watch? Bonus points if you can name the main character.
  60. Which is my favorite charity to support?
  61. Where do I volunteer my time in my community?
  62. When I'm on vacation, do I prefer to swim in the ocean or in the pool?
  63. We're going on a trip, and I get to choose the destination. Am I choosing the mountains or the beach?
  64. 1Do I prefer to ski on water or on snow and where's my favorite place to ski?

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 (or want to be in one), you should check out these articles:

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 teens to answer. If you're in a school setting, check out these “getting to know you” questions for students.

If you're looking for more introspective questions, here's our long list of questions to ask yourself to find out who you are.

Or maybe you just want to ask the people in your life some random questions.

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

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

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