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Important Questions for the Most Important People In Your Life

In our last episode, we talked about last-minute summer vacations with our best friends. In my experience, these trips are where the most bonding happens between me and my buds. I love learning everything I possibly can about my friends, so I have created an extremely long list of questions that are guaranteed to take your friendship to the next level. Some of the questions are tough, so feel free to skip and come back to the questions that are a little too tough at the beginning of the trip, and come back to them at the end. They are in no particular order, so you take the conversation where you want it to go.


This list can take hours and hours, so it is perfect for long car rides or late nights. With my closest friends, I enjoy trying to answer the questions for them as proof of how well I know them :)


Good Luck!


- Milan Gauthier


  1. What are you most proud of about yourself?

  2. What did you want to be when you were little? (firefighter, doctor, etc.)

  3. What’s your favorite SNL sketch?

  4. Describe your perfect day.

  5. What do you want to achieve in life?

  6. Who are your role models?

  7. If you could have dinner with three famous people who would they be?

  8. What was your favorite activity when you were a kid?

  9. Which parent is it easier for you to connect with?

  10. What makes you angry?

  11. What is your favorite tv show?

  12. What is the worst thing that has ever happened to you?

  13. What is your most prized possession?

  14. What movies make you cry?

  15. When do you feel strongest?

  16. What is your favorite book?

  17. What is your favorite dessert?

  18. What is your favorite cereal?

  19. What is the craziest thing you’ve ever done?

  20. What’s your relationship with your extended family?

  21. What’s your dream car?

  22. What have you been for Halloween?

  23. Have you ever been extremely sick?

  24. Have you ever had surgery?

  25. Would you ever dye your hair? If so what color?

  26. Do you get jet-lagged?

  27. What is the most serendipitous thing that has ever happened to you?

  28. Do you think of colors, numbers, or days of the week in colors? If so what colors are they in your head?

  29. What is your favorite stamp in your passport?

  30. When is your birthday?

  31. Do you prefer coffee or tea?

  32. What is your favorite Harry Potter book and movie?

  33. What is your favorite flower?

  34. What do you think you were in a past life?

  35. If there was a movie about your life what celebrity would play you?

  36. If you voiced a character in an animated movie or show, what would the character be like?

  37. Where would you live for a year if you could live anywhere with no consequences?

  38. Who was your favorite teacher?

  39. Which Marvel character would you want to play, who would you say you’re most like in the Marvel Universe?

  40. What’s your heritage?

  41. If you could change your name, what would you change it to?

  42. Do you have any nicknames?

  43. Who would you want to be president?

  44. Chocolate or fruity?

  45. Chocolate or vanilla?

  46. Cupcakes or cake?

  47. What’s your favorite candy?

  48. What is the thing you think about most? When you are zoned out, what is on your mind?

  49. What are your guilty pleasures?

  50. Are you a picky eater?

  51. Is your room usually dirty or clean?

  52. Do you believe in aliens?

  53. Favorite dog breed?

  54. Favorite Disney princess?

  55. Have you ever lived with anyone other than your family for an extended period of time?

  56. Are you good at art?

  57. Do you snore?

  58. Would you say you are a flexible person or do you need a plan?

  59. Who gives you advice about girls/boys?

  60. Do you have any secrets that only one person knows or that only you know? If so… what are they?

  61. Have you ever moved?

  62. Where were you born?

  63. How many cousins do you have?

  64. What do you do when you’re sad?

  65. Who was your best friend as a kid?

  66. Are you an introvert or an extrovert?

  67. What’s your favorite after school snack?

  68. What was the most trouble you’ve ever been in?

  69. Do you regret anything you’ve done?

  70. Do you think you are beautiful/handsome?

  71. Are you good at cooking?

  72. If you could live in any decade which would you choose?

  73. What’s your favorite season?

  74. What’s your favorite number?

  75. How do you feel about swearing?

  76. Are you religious?

  77. Do you want to have kids? How many?

  78. What do you want to name your kids?

  79. Do you like fashion?

  80. Who would you say is your fashion icon?

  81. Describe the moment in your life when you were the most scared.

  82. If money and qualification weren’t an issue what career would you have?

  83. If you could compete in the Olympics, what sport would you do?

  84. Do you like politics or do they make you uncomfortable?

  85. Who was the first person that you actually knew/loved that died?

  86. Who was your first kiss?

  87. What happened during the kiss, what was it like?

  88. What is your favorite scent?

  89. What grosses you out?

  90. Can you handle blood and needles?

  91. Have you ever been depressed?

  92. How often have you laughed so hard your stomach hurts and you can’t stop?

  93. What is the worst nightmare you’ve ever had?

  94. What is the best dream you’ve ever had?

  95. Who is your favorite book character that you can relate the most to?

  96. Do you prefer showers or baths?

  97. Do you have a diary?

  98. Have you ever been skinny dipping?

  99. What games did you play on the playground when you were a kid?

  100. What is your dream house like?

  101. Who is your best friend now?

  102. Would you rather hang out with a group or one on one?

  103. Do you believe that everyone has one soulmate?

  104. Do you believe in ghosts?

  105. Has something completely inexplicable ever happened to you?

  106. Do you think you could survive solitary confinement?

  107. Do you believe in astrology?

  108. If you could have any superpower what would it be?

  109. Did you buy your first car?

  110. Do you/did you get an allowance from your parents?

  111. What jobs have you had? Or what was your first job?

  112. Fruits or vegetables?

  113. Favorite fruit?

  114. Have you ever had a near-death experience?

  115. What are the hottest and coldest temperatures you’ve ever been in?

  116. What question were you hoping would come up?

  117. How many Instagram accounts do you have?

  118. What is your favorite state?

  119. Do you have any secret talents?

  120. Name every country you have been to.

  121. Do you think the world is going to end? If so when?

  122. Do you enjoy meeting new people?

  123. If you could have another sibling would you want a brother or sister? Younger or older?

  124. What would you do if it was the last 24 hours of your life?

  125. What’s the biggest lie you have ever told?

  126. How long is the longest you’ve stayed awake for?

  127. Did you have braces?

  128. Do you play video games?

  129. Favorite movie quote that makes you laugh.

  130. Tell a funny story of something you did when you were little.

  131. Have you seen someone die/seen a dead person?

  132. When do you feel like you are most in your element?

  133. When does the time go by fastest for you?

  134. When does the time go by slowest for you?

  135. Is there something about yourself that you don’t like?

  136. When you’re mad what song do you listen to?

  137. Where do you go when you want to be alone?

  138. If you won the lottery what would you buy?

  139. Do you prefer to have people over to your house, or to go to theirs?

  140. Have you ever performed on stage?

  141. Do you like soda?

  142. Gale or Peeta?

  143. Do you know anyone famous?

  144. Have you ever driven drunk people?

  145. Have you ever driven drunk/intoxicated?

  146. How many grandparents do you have?

  147. Who’s your celebrity look alike?

  148. What’s the nicest thing someone has ever done for you?

  149. Do you like school dances?

  150. Have you ever visited someone in jail?

  151. Who do you get annoyed with first in your family?

  152. Last?

  153. What makes up most of your saved posts on Instagram?

  154. Can you drive a manual?

  155. Do you think you could do an hour-long Ted talk on any subject? What one?

  156. What are your family members' names?

  157. Have you ever been addicted to something?

  158. Do you have any recurring dreams?

  159. Favorite SNL character?

  160. Least favorite TV show?

  161. Do you like driving?

  162. Would you rather live alone or with others?

  163. If you could live in any book or movie world where would you live?

  164. What’s your middle name?

  165. What are some of your family's last names?

  166. Who is your celebrity crush?


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