239 Deep + Unique “How Well Do You Know Me” Questions

This post is a GIANT list of “how well do you know me” question ideas.

The more time that you spend with your friends, family members and spouse/partner, the more random details that they will naturally pick up about you.

Like the things that annoy you… The things that inspire you…. The foods you love… Your favorite childhood memory… 

The question today is… Have you ever put their knowledge of you to the test??

One simple way to do that is to play a round of “how well do you know me”?

As an activity, it’s pretty simple- you ask another person questions about yourself and if they get the answer correct (judged by you) then YAY!
If they don’t, then it becomes a learning opportunity. You have to tell them the right answer.

(You can also make it a drinking game where if the other person guesses right, YOU drink and if they don’t, then THEY drink).

Another way to use “how well do you know me” questions is to make them into trivia party games for a party that celebrates you (like your bachelorette party, bridal shower or birthday party for example).

It’s a fun way to get personal, silly, vulnerable, and deep with people that already know you really well (or not so well)!

Below, I’ve compiled a long list of questions, in four categories, to help you get started.

20 Quick & Fun Quiz Questions For Anyone

At some point, you will find yourself in a situation where you want to create a short quiz or questionnaire about yourself.

For example, you may want to quiz your Instagram followers or Youtube subscribers. Or, like I said above, you may want to create a multiple choice trivia party game.

In situations like these, you will love these 20 quick, fun & funny questions for anyone to answer.

1. If I could choose a single house chore to do for the rest of the month, what would it be?

2. Who would I be if I could be any of the past presidents for a day?

3. If I could go back to a particular time period, what era would I choose?

4. If I could swap lives with any celebrity, who would it be?

5. If every day could be a holiday of my choice, what holiday would I pick?

6. If I could only wear one outfit for a week straight, what would I wear?

7. If I had to decide between shopping online or in a store, which would I choose?

8. If I had to choose between waffles and pancakes, which would I choose?

9. Would I rather save money or spend money?

10. Do I prefer to live in the country or the city?

11. Do I prefer to be an entrepreneur or an employee?

12. Do I prefer to drive or be driven?

13. If I had to choose only one, would I prefer heels or sneakers?

14. If I had to choose only one, would I prefer jeans or sweatpants?

15. If I could only choose one, would I prefer having more money or more friends?

16. If I had to choose between DC and Marvel forever, which one would I choose?

17. Would I prefer to journey to outer space or to delve deep into Earth’s oceans?

18. If I could choose one of the 5 senses to be heightened for a day, which one would it be?

19. If I had a magic lamp, what would my three wishes be?

20. Would I prefer to be too tall or too short?

104 “How Well Do You Know Me” Questions
FOR FRIENDS

Friends are a significant part of our lives, and sometimes, we are closer to them than our own blood relatives. Best friends often know things about us that we are hesitant to reveal to family members.

Below, you will find 104 how well do you know me questions for best friends, so that you can test your knowledge of each other. Remember- it’s okay to answer questions wrong. The point of the game is to learn and unlearn things about each other, in a fun way. That’s the whole point of friendship!

21. What’s my full name? (all the middle names and everything)

22. If you could describe me in three words, what would those words be?

23. What word would I use to describe the nature of our friendship?

24. What’s my most embarrassing moment?

25. Am I a cat person or a dog person?

26. Would you describe me as a daring person or as a scaredy-cat?

27. What is my dream car?

28. What is my favorite social media platform to use?

29. Am I, or am I not a rule breaker?

30. If I ever met a celebrity, what would be my first reaction?

31. What is my biggest secret?

32. What are my three favorite hobbies?

33. What is my hidden talent?

34. What is my biggest fear?

35. What am I allergic to?

36. What are my pet peeves?

37. What is my biggest regret?

38. If I could travel to any place in the world, where would it be?

39. What is the name of my imaginary boyfriend?

40. How many kids do I want to have in the future?

41. What are my insecurities?

42. Would I rather drink tea or coffee?

43. What was my favorite thing to do in college?

44. How many languages can I speak?

45. What was my first job ever?

46. Who was my first kiss?

47. What is my Myers-Briggs personality type?

48. Who is my favorite KarJenner?

49. How old am I?

50. How could you tell that we would be great friends?

51. How did we meet?

52. What was my favorite subject in high school?

53. What religion do I practice?

54. What’s my nationality?

55. When is my birthday?

56. What is my favorite movie?

57. What is one thing that I can’t live without?

58. How many siblings do I have?

59. What is my screen saver?

60. What is my favorite game to play?

61. What was my favorite childhood cartoon?

62. What is my favorite anime?

63. Am I an introvert or an extrovert?

64. What song makes me cry?

65. Which movies have made me cry?

66. Do I have an entrepreneurial drive?

67. Do my work colleagues or boss give me a hard time at work?

68. What is my favorite color?

69. What is my least favorite color?

70. What is my favorite restaurant?

71. What organizations was I part of in college?

72. What GPA did I graduate with from college?

73. Was I ever valedictorian, either in high school or college?

74. Who is my favorite male celeb crush? 

75. Who is my favorite female celeb crush?

76. Am I good with money or bad with money?

77. What kind of a drunk am I?

78. How do I handle difficult situations?

79. Do I keep it cool under pressure?

80. What political party do I support?

81. What inspires me? 

82. What is my best trait?

83. Have I ever said something that hurt you unintentionally?

84. What is the worst thing I have ever done?

85. Have I ever had a crush on your brother? 

86. Have I ever had a crush on your sister?

87. Have I ever had a near-death experience?

88. Have I ever lost someone dear to me?

89. Who is my favorite artist (that is alive right now)?

90. Do we share the same taste in men?

91. Do we share the same taste in women?

92. What is my favorite store to shop at?

93. Which do I prefer: skirts & dresses or pants & leggings?

94. What is the funniest thing I have ever said?

95. How many birthmarks do I have?

96. When did I get my first kiss?

97. What was my major in college?

98. What is the first thing I do when I wake up every morning?

99. Do I keep a journal?

100. What is my favorite genre of music?

101. Who do I think is the greatest artist of all time?

102. What is my favorite soccer team?

103. What is my favorite baseball team?

104. What is my favorite American football team?

105. Who is my favorite female athlete?

106. Who is my favorite male athlete?

107. What was the first concert I ever attended?

108. Whose concert would I love to attend the most right now?

109. What sport(s) did I play in high school?

110. Did I play an instrument in high school? If so, what instrument did I play?

111. What is my take on meritocracy?

112. If I could change the world, what would be my first action?

113. What is my favorite emoji?

114. Where do I see myself in the next five to ten years?

115. What is my favorite book, and why do I love it?

116. What is my favorite season, and why do I love it?

117. Who is my favorite YouTuber?

118. What is the most expensive thing I own?

119. What is my favorite body part? 

120. How tall am I?

121. How much do I weigh?

122. What is my favorite way to unwind after work?

123. What is my coping mechanism when I feel angry?

124. What is the wildest thing I have ever experienced?

61 “How Well Do You Know Me” Questions
FOR COUPLES

Are you eager to find out how well your partner knows you? Or how well you know them? Would you like to share in-depth knowledge of your lives before and with each other?

This collection of ‘how well do you know each other’ questions for couples is your opportunity to do that.

This is a stimulating game to play on date nights with your significant other or as conversation starters at dinner or in the car.

125. Had I ever been in love before you? 

126. How many people have I dated?

127. What is my love language?

128. What is my job title?

129. What do I do in a typical workday?

130. Do I love or loathe my job?

131. How can you tell when I am angry?

132. Am I passive-aggressive, calm and collected, or brash and straightforward?

133. What do I like the most about you? 

134. When did I fall in love with you?

135. What color are my eyes? 

136. How many tattoos do I have? 

137. Can you name the location of each tattoo?

138. What is my most attractive feature?

139. What are my erogenous zones?

140. Do I believe in zodiac signs?

141. What is my zodiac sign?

142. Where is my dream vacation destination?

143. What is my dream job?

144. When do I feel the sexiest? 

145. Between you and I, who is the better kisser?

146. Am I a morning person or a night owl?

147. Do I have any dating rules? If so, what are they?

148. Which do I prefer: the dessert or the entrée?

149. What is my favorite dessert to have?

150. If I had a billion dollars, what would I do with it?

151. If I could live anywhere else in the world permanently, where would I live?

152. What superpower do I wish to have?

153. What do I like to do when I am feeling stressed out? 

154. Do I know how to swim?

155. Do I prefer to sleep naked, in lingerie, or in pajamas?

156. Do I have nieces and nephews?

157. How many dogs does my family have?

158. What position am I among the children in my family?

159. Do I plan to get married in the future?

160. Do I plan to have kids in the future?

161. Do I have a criminal record?

162. Do I get carsick or seasick?

163. Do I like road trips?

164. What is my favorite reality show?

165. Do I enjoy the beach?

166. Do I enjoy hiking?

167. Have I ever run a marathon?

168. Have I ever been on a cruise ship?

169. What is my biggest motivation?

170. Do I like or hate spicy food?

171. Who do I admire the most in the world?

172. Do I have a retirement account?

173. What do I think about aliens?

174. Have I ever experienced heartbreak?

175. Do I believe in the theory of evolution?

176. Have I ever fainted?

177. Have I ever had surgery?

178. What’s the most embarrassing trend I’ve ever been a part of?

179. What is my most successful DIY project?

180. Do I like PDA (public displays of affection)?

181. Have I ever kissed someone on the first date?

182. Do I believe in love at first sight?

183. How many musical instruments can I play?

184. What is my favorite flavor of ice cream?

185. What has been my most life-changing experience so far?

54 Questions For Family Members
(Sibling Tag Questions)

The relationship we have with our family members can be very dynamic. You might be surprised to learn that there’s a lot you don’t know about your siblings or parents, even though you’ve spent most of your life together.

Here are 55 fun questions to ask your family members when you’re hanging out together. (These are also questions that you can use for sibling tag on social media).

186. Who is the messiest family member?

187. Who is the most troublesome? 

188. Who has ever gotten into a physical fight? 

189. Who got in the most trouble as kids? 

190. What did they get in trouble for? 

191. Which sibling is the most likely to end up in jail? 

192. Did I ever steal your things? 

193. What did we fight over the most as kids?

194. How many boyfriends have I had or How many girlfriends have I had?

195. What are my weird habits?

196. Who is the noisiest among us all?

197. As a child, what did I want to be when I grew up?

198. Have I ever failed a class in school?

199. Who would I have loved to go to prom with?

200. Who was my favorite girl group when I was younger? Who was my favorite boy band as a kid?

201. Who did I get married to when I was five?

202. Did I ever get sent to detention?

203. What are the names of my closest friends?

204. What was my favorite thing to do as a kid?

205. What was my favorite show as a kid?

206. What was I the most scared of as a kid? Am I still scared of it now?

207. Am I street smart or book smart?

208. Who is the most considerate sibling?

209. What was my favorite thing to wear when I was younger?

210. Who is the most protective sibling?

211. What was my favorite pet?

212. What day of the week was I born?

213. How much did I weigh when I was born?

214. Who always has a stash of food hidden away in their room?

215. Who sleeps the most?

216. Which sibling is most late to events?

217. What is the best prank I’ve ever pulled?

218. What am I most proud of? 

219. In a zombie apocalypse, which sibling would you choose as your survival partner?

220. Who is my favorite family member?

221. Which household chore do I hate doing the most?

222. Am I more similar to mom or to dad?

223. If we tried, do you think that I could pass as your doppelganger?

224. What is my favorite movie genre?

225. What’s my favorite game to play at BBQs?

226. Am I a good person?

227. Have I ever been peer pressured by friends?

228. Have I ever made our parents cry?

229. Have I ever made any of you cry?

230. Am I scared of horror movies?

231. Have I ever skipped school?

232. Have I ever forgotten your birthday?

233. What is the most meaningful gift I have ever given you?

234. At what age did I stop believing in Santa Claus and the Tooth Fairy?

235. Have you ever been in a serious incident and didn’t reach out to any of us?

236. Have I ever snuck out of the house?

237. What is the biggest lie I ever told growing up?

238. Who was my favorite teacher at school?

239. What did I think was so cool as a kid, but now cringe at when I look back on it?

240. What is my favorite food to eat?

241. What were my favorite type of clothes to wear growing up?

Test your friends, significant other, or siblings using the questions above. You are sure to have meaningful conversations afterward that will draw you closer in ways that you could never have imagined.