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215 Deep Questions To Ask Friends To Get To Know Them Better

A photo of Tom who is the Co-Founder of Questions About Everything

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These questions to ask friends are great to ask close friends you’ve known for years and those you’ve just become friends with.

We’ve got a range of things to talk about with your friends in this article. From how well you know each other, to some deep talking points about life, you’ll have hours of interesting conversations ahead of you.

Sometimes it can be hard to find questions to ask a friend, especially when you know them so well. Even if you’re new friends, these questions will help to cement your friendship for years to come.

Check out our list of questions to ask your friends and start having some fun conversations today!

Deep Questions To Ask Your Best Friend

1. Why do you think we are best friends?

question to ask friends on why you're best friends

2. If you could stop time for one hour and you could do anything whilst time was still, what would you do?

3. What’s the most embarrassing thing that’s ever happened to you?

4. What were your first impressions of me when we first met?

5. Out of the two of us, who do you think knows the other person the best?

6. Would you ever tell me a lie to protect me, or is honesty always the answer?

7. What do you think is the most important aspect in ensuring a friendship remains strong?

8. What song do you think we both love and would remind you of me?

9. Do you feel like you challenge yourself to get out of your comfort zone enough?

10. What do you think is the most important trait a good friend can have?

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11. Do you see a point in the future where we’re no longer friends?

12. Do you think you have enough friends, and how many is too many?

13. What are the three places on your bucket list you can’t wait to visit?

14. Do you feel like you can talk to me about anything?

15. Do you feel it’s easier or harder to make new friends the older you get?

16. What’s your favorite memory from our friendship so far?

17. If you won $1 million, what would you do with the money?

18. Do you like to spend time on your own, or do you prefer to be around other people?

19. If you could move to any country in the world, where would you go?

20. If you had to describe me in three words, what words would you choose?

21. Do you think a boy/girl could get in the way of our friendship?

22. What’s the luckiest thing that’s ever happened to you?

23. Who do you think is the funniest person in our friendship group?

24. Is there anything about me that might surprise you if I told you? Or do you feel you know me that well nothing would surprise you?

25. If you had to eat one meal for the rest of your life, what it would be?

Funny Questions To Ask Your Friends

26. Who is the most annoying person you know?

A question to ask friends about who's the most annoying person you know

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27. What’s the funniest joke you know?

28. Out of the two of us, who hates losing the most?

29. Out of our friendship group, who would be best equipped to survive in the jungle?

30. If you had a superpower, what would it be and why?

31. If you had to bathe in food, what food would you choose?

32. Would you rather never shower again or never laugh again?

33. What’s the best practical joke you’ve been a part of?

34. Would you rather have toes for fingers or three eyes?

35. If you could be reincarnated as any animal, which one would it be?

36. Have you ever accidentally been caught stalking anyone on social media?

37. Have you ever had a crush on one of your friend’s lovers?

38. What’s your guilty pleasure?

39. What song do you know every single lyric to?

40. What do you think is the weirdest food combination ever invented?

41. What’s your favorite word?

42. Have you ever cried due to laughing so hard? What happened?

43. What goes on the sandwich first, peanut butter or jelly?

44. Do you think sarcasm is funny?

45. What is your best accent impression that you can do? Please do it?

Questions To Ask Friends To Get To Know Them Better

Maybe you think you know your friends, or maybe you’ve just met a new friend and want to get to know more about them.

This section is similar to our questions to get to know someone and will help you develop stronger bonds with your friends no matter how old the friendship is.

46. Do you feel happy in your life as it is right now?

47. What are your goals and ambitions for life?

48. What career do you want, if it isn’t the one you are now?

49. Do you have any desires that you hope to achieve but that scare you at the same time?

50. What was your upbringing like?

51. What are your family traditions like, and which are the most special ones?

52. Do you feel you always tell your whole truth, or do you feel you shrink your opinions to fit in?

questions to ask your friends telling the truth

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53. What are your favorite things to do when you’re on your own?

54. If you could do any one thing to help the planet, what would you do?

55. What would you do in a volunteer role to help the community?

56. If you could run the country, what would you do?

57. Do you feel like you could ever stop eating meat?

58. Do you get sick often?

59. What are your favorite books, and what would you recommend?

60. Are you an introvert or an extrovert?

61. How are you at losing? Do you think you take it well, or are you competitive?

62. What makes you laugh the most?

63. Do you like nature and the outdoors?

64. Do you like clowns?

65. Do you like getting dressed up for formal parties?

66. What do you love most about our friendship?

67. What’s the worst movie you have ever watched?

68. What do you want to do with your life, and do you think you can do it?

69. What’s your favorite historical time to learn about?

70. What’s your favorite Disney film and character within that film?

Deep Questions To Ask Friends

This section has some more introspective questions you can ask your friends.

These deep questions to ask will lead to some lively and thoughtful conversations that will last for hours.

71. What trends do other people love, but do you hate?

72. Are you good with technology, and do you think it’s taking over the world?

73. Do you ever feel like society is falling apart?

74. What’s the most beautiful thing you love about life?

75. Do you consider yourself a judgemental person, and do you ever change your first impression of someone?

76. How stubborn are you?

77. Do you think happiness is more important than wealth?

78. Do you ever wish you were born in another part of history?

questions to ask your friends wish you were born in a different part of history

Next: Topics to talk about

79. How do you feel about tattoos, and do you have any?

80. What disease are you scared of?

81. Have you ever forgiven someone when you couldn’t move on from it and regretted it after?

82. What makes the perfect relationship?

83. What’s your meaning of rub?

84. How are you at waiting, or are you an impatient person?

85. Do you feel like you spend enough time in the present moment, or are you always preoccupied with the future or past?

86. When was the last time that you experienced pure magic, and what happened?

87. What’s your biggest turn-off?

88. What’s your biggest turn on?

89. What thing do you own in your life that is the most sentimental to you?

90. Do you love yourself enough?

91. Do you find joy in small moments, and if so, what are those moments?

92. Are you a perfectionist, or do you like to go with the flow?

93. How are you with uncomfortable conversations?

94. What philosophical questions keep you up at night?

95. Do you appreciate art?

96. Are you spiritual? If so, what spiritual practices do you take part in?

97. What are your goals for the next six months?

98. What emotions do you do your best to avoid or feel the most uncomfortable experiencing?

99. What’s the worst thing that happened to you but that you grew the most from, so ended up being happy that it happened?

100. Do you believe in karma?

Questions To Ask Your Friends To See How Well You Know Them

101. What’s my favorite food?

102. What’s my pet hate?

103. Am I close to my family, and who am I closest to?

104. Do you feel like I would survive on a desert island by myself?

questions to ask your friends survive on a desert island

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105. Do you think I am generous?

106. What’s my dream job?

107. What are my biggest ambitions, and do you think I will achieve them?

108. What are my biggest challenges in life?

109. Do you consider me to be a confident person?

110. What one meal would I eat for the rest of my life if I could only choose one?

111. What foods do I hate?

112. Do I like dogs, and have I ever owned any?

113. Am I more of a dog or cat person?

114. Do I have a healthy diet?

115. Who’s my best friend?

116. How shy am I?

117. Who was my first love?

118. Do you think I am likely to get married?

119. How important is it to me to have children, and how many would I have?

120. What has been the most life-changing event of my life?

121. Have I ever been in hospital?

122. Do I care about the planet?

123. What song am I likely to know all the words to?

124. Do you think I am an honest person?

125. Would you trust me with a secret, and why?

Personal Questions To Ask Friends

126. Have you ever been in hospital?

127. What makes you cry the most?

128. What’s the one thing that keeps you awake at night with worry?

129. What do you do to relax?

130. Who do you look up to the most in your life?

questions to ask your friends who do you look up to

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131. What was the last good deed that you have done for someone?

132. How often do you spend on social media?

133. What do you watch most on YouTube?

134. What gets you angry?

135. What are your biggest fears?

136. Which political party do you follow?

137. Who’s your celebrity crush?

138. What has been your best intimate experience, if any?

139. What turns you on the most?

140. What traits do you look for in a partner?

141. Have you ever lied about a part of yourself to fit in?

142. Do you speak your ultimate truth?

143. When you die, would you rather be buried or cremated?

144. What would you change about yourself?

145. What do you feel you need help with but are too embarrassed to ask for help with?

146. Do you ever worry about the future?

147. Are you good with money?

148. What would you change about your body?

149. What’s your favorite thing to do at the weekend?

150. Who could you spend all day with and never get bored?

General Questions To Ask Your Best Friend

151. Who inspires you the most?

152. Who’s life do you look at and wish you had their life?

153. Would you ever join the military?

154. Would you ever travel into space if you had the opportunity?

155. Do you feel like humanity protect the planet enough?

156. What is your best memory from childhood?

questions to ask your friends best childhood memory

Next: Christmas conversation starters

157. Do you think your life is exciting or boring?

158. If you were going to have a job on the side, what would it be?

159. Do you prefer buying expensive gifts for people, or making them yourself?

160. What’s your favorite thing to cook?

161. What would be your ideal proposal?

162. What has been your most disappointing situation?

163. What do you think are the best activities you can do with friends?

164. Do you ever try to improve yourself or parts of yourself that you don’t like?

165. What do you miss from childhood?

166. Have you ever done an all nightery to finish a piece of work?

167. Have you ever snuck out of the house as a child when your parents thought you were in bed?

168. Would you ever climb Mount Everest?

169. Who do you look at the most on Instagram or social media?

170. Can you dance?

171. In secret, do you have any weird things you do that you wouldn’t ever speak about?

172. Do you ever pretend you are busy when you don’t want to go to something?

173. Have you ever told a white lie to protect one of your loved ones?

174. Are you good at apologising when you are wrong about something or made a mistake?

175. How many children would you like to have?

176. Do you think your career is more important than relationships?

177. What’s your biggest bugbear about society?

178. Do you think it’s right that you work until you’re retired, and then you can enjoy yourself, is this something you feel like you fit in to?

179. If money was no object, how would you spend your days?

180. What influencer inspires you the most?

Questions To Ask Your Old School Friends

181. What do you think has been the biggest challenge since we left school?

182. Are you where you hoped to be by now?

questions to ask your friends are you where you hoped to be in life

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183. What was the best memory you had from school that you will never forget?

184. Do you remember anything silly we did in school?

185. What songs did we use to love in school?

186. What were school discos and proms like? Do you remember them well?

187. Are you friends with anyone now that you didn’t like in school?

188. What about you has changed the most since we left school?

189. Have you stayed friends with everyone from school?

190. Who do you think has changed the most out of the people we went to school with?

191. Is there anybody you think has been the most successful since we left school that you didn’t expect to be?

192. Who did you not find attractive in school that you think is good looking now?

193. What do you most regret from your school years?

194. If you could turn back time, what would you change since leaving school?

195. Do you remember any of our teachers?

196. Do you think you partied enough in school or too much?

197. Do you think that I have changed a lot since school?

198. What was your worst memory about going to school?

199. Did you like school?

200. Do you think we’ll remain friends for the rest of our lives?

201. Why do you think we have managed to stay friends for this long?

202. What did you first like about me when we met in school?

203. Do you still want to achieve the same things you thought you did when you were younger?

204. Are you more or less excited about the things you got excited about back then?

205. What’s your funniest memory of us in school?

206. How many times do you think about memories from school?

207. Did you ever tell your high school crush you liked them?

208. What do you miss most about our school years?

209. If you could live one memory from school again, what would it be?

210. When you look back, what do you wish you would’ve tried harder at?

211. Do you ever get embarrassed about the dress sense you had back in school?

212. Do you remember where we used to hang out outside of school?

213. What do you hope to achieve in the next five years of your life?

214. What still makes you laugh now when you think about it?

215. Did you ever find any of our teachers attractive?

Looking For More Questions?

Fun questions to ask – Have some fun conversations with your closest friend that will have you in stitches.

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.