“Help! My son (or daughter) never talks to me.”  

This question, or some variation of it, is one of the most frequent complaints I receive from parents of tween-to-teens.  This is often followed by, “My kid never listens to me!” The truth is that most adolescents don’t talk or seem like they are listening. Why? Often, they aren’t being spoken to; rather, they are nagged, disciplined, instructed. Rarely do they feel like anyone is speaking or listening to them. If kids don’t feel they can talk to you about little things, they will never come to you with the big stuff.

Carve out moments throughout the week to have open, comfortable, even silly conversations with your child. Not only will it help foster better communication in your relationship, it will help your child develop greater confidence and self-esteem.

Here are 225 conversation ideas (in no particular order) to get you started. If you have one you’d like to share, please add it to the comments.

  1. What is your favorite / least favorite word? Why?
  2. When did you last lose your temper?
  3. What’s your favorite birthday memory?
  4. How important is a birthday celebration to you?
  5. What’s your favorite way to celebrate a win?
  6. What are you most grateful for?
  7. If you were on a deserted island what 3 things would you take?
  8. Do you remember your dreams?
  9. What was your most recent dream about?
  10. Who do you most respect? Why?
  11. Do you think respect should be earned?
  12. How can someone earn respect?
  13. What are you looking forward to this school year?
  14. What’s your favorite way to unwind
  15. What’s your all time favorite dessert? 
  16. Who is your favorite YouTuber?
  17. What’s your favorite social media platform? Why?
  18. What videos have you been watching non-stop lately? 
  19. What do you want to make happen over the next year? Month? Year?
  20. What frustrates you most?
  21. Where’s your dream travel destination?
  22. What’s your favorite season or holiday? What do you love about it?
  23. How does your ideal day begin?
  24. What makes you happy?
  25. What was/is your favorite class in school? 
  26. What’s your favorite quote?
  27. What book have you read more than once? 
  28. What idea excites you?
  29. Who would you most like to ask for a piece of advice from? 
  30. Who is your hero?
  31. If you could live anywhere, where would it be?
  32. What is your biggest fear?
  33. What is your favorite family vacation?
  34. What would you change about yourself if you could?
  35. What really makes you angry?
  36. What motivates you to work hard?
  37. What is your favorite thing about your career?
  38. What is your biggest complaint about your job?
  39. What is your proudest accomplishment?
  40. What is your child’s proudest accomplishment?
  41. What is your favorite book to read?
  42. What makes you laugh the most?
  43. What was the last movie you saw?
  44. What did you want to be when you were small?
  45. What does your child want to be when he/she grows up?
  46. If you could choose to do anything for a day, what would it be?
  47. What is your favorite game or sport to watch? Play?
  48. Would you rather ride a bike, ride a horse, or drive a car?
  49. What would you sing at Karaoke?
  50. If you could only listen to one radio station or one type of music for the rest of your life, what would it be?
  51. Which chore would you rather do: wash dishes, fold the laundry, mow the lawn, clean the bathroom, or vacuum the house?
  52. If you could only eat one meal for the rest of your life, what would it be?
  53. Who is your favorite author?
  54. If you could go back and repeat one year of your life, which year would it be?
  55. What is something you would like to learn?
  56. Do you feel like you are a good listener?
  57. What is your all-time favorite TV show?
  58. What is something you want to do before you die?
  59. What is on your “bucket list?”
  60. What are the three most important things in your life?
  61. Who are the 5 people you spend the most time with?
  62. What talent would you most like to have?
  63. Nicknames: yay or nay?
  64. What do you worry about?
  65. Do you like or dislike surprises? Why or why not?
  66. Would you rather vacation in Hawaii or Alaska, and why?
  67. Would you rather win the lottery or work at the perfect job? And why?
  68. Who would you want to be stranded with on a deserted island?
  69. If money was no object, what would you do all day?
  70. If you could go back in time, what year would you travel to?
  71. How would your friends describe you?
  72. What is the best gift you have been given?
  73. What is the worst gift you have received?
  74. Aside from food, water, and shelter, what one thing could you not go a day without?
  75. List two pet peeves.
  76. Where do you see yourself in five years?
  77. If you were a super-hero, what powers would you have?
  78. What would you do if you won the lottery?
  79. What form of public transportation do you prefer? (air, boat, train, bus, car, etc.)
  80. What’s your favorite zoo animal?
  81. If you could go back in time to change one thing, what would it be?
  82. If you could share a meal with any 4 individuals, living or dead, who would they be?
  83. What’s the longest you’ve gone without sleep (and why)?
  84. Would you rather trade intelligence for looks or looks for intelligence?
  85. Have you ever had a secret admirer?
  86. What’s your favorite holiday?
  87. What’s the most daring thing you’ve ever done?
  88. What’s your favorite type of foreign food?
  89. What’s the most unusual thing you’ve ever eaten?
  90. What kitchen appliance do you use every day?
  91. What’s your favorite fast food chain?
  92. What’s your favorite family recipe?
  93. What is your favorite thing to eat?
  94. What is one food that you will not eat?
  95. Describe the perfect party.
  96. What is your favorite type of art?
  97. What sport do you think you are the best at?
  98. What was the last book you read?
  99. What’s your favorite magazine? book?
  100. What’s your favorite movie? Actor? Actress?
  101. If you write a book, what would it be about? What would title it?
  102. Which is your favorite song? Singer? Band?
  103. In the evening, would you rather play a game, visit a friend, watch a movie, or read?
  104. What’s one book that you think everyone should read?
  105. Do you want to be famous?
  106. If you could become a character in a TV show or movie, who would you chose to be?
  107. Who would you want to play you in a movie of your life?
  108. If you could be a cartoon character, who would you want to be?
  109. Tell me one. 
  110. What is the one thing that makes you laugh the hardest?
  111. What is your favorite way to exercise? Least favorite?
  112. How long does it take you to get ready in the morning?
  113. What’s your favorite family tradition?
  114. What is your favorite childhood memory?
  115. Is your glass half full or half empty?
  116. What’s the craziest thing you’ve done in the name of love?
  117. What three items would you take with you on a deserted island?
  118. What was your favorite subject in school?
  119. Do you collect anything?
  120. Is there anything you wished would come back into fashion?
  121. Are you an introvert or an extrovert?
  122. Which of the five senses would you say is your strongest?
  123. Have you ever had a surprise party? (that was an actual surprise)
  124. Are you related or distantly related to anyone famous?
  125. Does your family have a “motto” – spoken or unspoken?
  126. Who was your favorite teacher in school and why?
  127. What three things do you think of the most each day?
  128. If you had a warning label, what would yours say?
  129. What song would you say best sums you up?
  130. What celebrity would you like to meet at Starbucks for a cup of coffee?
  131. Who was your first crush?
  132. What’s the most interesting thing you can see out of your office or kitchen window?
  133. On a scale of 1-10, how funny would you say you are?
  134. Where do you see yourself in 10 years?
  135. What was your first job?
  136. If you could join any past or current music group which would you want to join?
  137. How many languages do you speak?
  138. What is your favorite family holiday tradition?
  139. Who is the most intelligent person you know?
  140. If you had to describe yourself as an animal, which one would it be?
  141. How do you define honesty?
  142. What is your biggest fear or worry?
  143. What is the main thing that makes you unique?
  144. If you had to evacuate our house, what would you grab on the way out?
  145. What facial expression or movement do you do when you are lying?
  146. What is the oldest item you own?
  147. If someone was giving you a gift (money is no object), what would you want to receive?
  148. Would you rather watch the sunrise or the sunset? Why?
  149. What does it mean to have courage?
  150. Do you like your name?
  151. If you could change you name, what would you change it to?
  152. What is your greatest strength?
  153. What is your worst weakness?
  154. If you could predict the future, what would you do with that knowledge?
  155. Is your favorite time the past, present or the future?
  156. Where do you see yourself in 20 years?
  157. Who is the one person that helped to make you who you are today?
  158. If you were punished for a crime, what type of punishment would you choose? 
  159. Describe a time you got into trouble.
  160. What do you do when you first wake up in the morning?
  161. What makes you a good person?
  162. What would your obituary say?
  163. What is your greatest regret? 
  164. How would you describe standing on a beach looking at the ocean?
  165. What is your favorite outfit to wear?
  166. What do you do when you are driving alone in a car?
  167. If a friend is being bullied or harassed by someone, what do you do?
  168. Reflect on the characteristics of your best friend. What makes him or her so special?
  169. Can you keep secrets? Describe a time you didn’t.
  170. How do you show your love for others?
  171. What is the nicest thing anyone has ever done for you?
  172. If you could become anyone’s friend that you want, who would you choose?
  173. Are you the type of person with lots of friends or just a few close ones?
  174. What is one quality you admire most in others?
  175. Do you prefer to be with those who are younger or older than you are?
  176. If you could ask me one question, and I had to answer you truthfully, what would you want to know?
  177. What is the meanest thing you have ever done to someone?.
  178. Who is one friend from your past you want to reconnect with?
  179. When did you kiss for the first time and what was it like?
  180. Describe an activity that you think is truly romantic.
  181. When you are in trouble, whom do you call for help?
  182. Who are the people you love the most?
  183. If you could speak any language, what would it be and why?
  184. If you had to pick one place in your town to bring a tourist, where would you go?
  185. What is the one cause that you feel most passionate about?
  186. If you lived in the pioneer days, would you have traveled west or stayed put in the east?
  187. If you found a genie in a bottle, what three things would you wish for?
  188. What are five thing that would make your life easier?
  189. Which is your favorite non-profit organization or cause?
  190. If you could travel to space, would you go?
  191. If you could move anywhere, where would you go and why?
  192. Would you want to travel the world on a boat in the sea?
  193. When you travel away from home, do you miss it?
  194. What is the greatest crisis we face as a world?
  195. If you could write your own bill of rights, what would you include?
  196. What is going on today in the world that affects you the most?
  197. What bad habit would you be willing to give up if it guaranteed you’d live to be 100?
  198. What are your bad habits?
  199. If you could have someone else’s face, whom would you choose?
  200. What physical feature do you least like about yourself?
  201. Would you want to know the exact day of your death?
  202. Would you describe yourself as a ‘people person?’
  203. What three things make you happiest?
  204. If you could pick one thing to change about school, what would it be?
  205. Are you the kind of person who wants to be the big fish in a little pond or the little fish in the big pond?
  206. Describe a time when you wanted to quit, but didn’t.
  207. Is competition good for you?
  208. What is something you learned in school that you think is useless to you today?
  209. If you could pick any career, what would you want to be?
  210. What is your favorite outside activity?
  211. If you had to spend a day not using any technology, what would you do?
  212. What makes our family unique from others?
  213. What was the hardest part about being a kid?
  214. What are some of your favorite traditions?
  215. Do you know how you got your name?
  216. Do you think you take after anyone in the family?
  217. What is one thing you will never do again?
  218. Who knows you the best?
  219. What is the best life lesson you have learned?
  220. What do you like most about yourself?
  221. What’s a special memory you have with an extended family member?
  222. If you only had one year to live, what if anything, would you do differently?
  223. Do you look more at the facts or your feelings when making a decision?
  224. What do you want to do?
  225. What’s one thing that you need from me?

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