1. What would be the absolute perfect day?

2. What did you learn a little too late?

3. What are you too hard on yourself for?

4. What do you most look forward to about getting old?

5. What is something you tried really hard to like but didn’t?

6. What makes you different from most people?

7. Is it more important to love or to be loved?

8. What’s one difference between us that you absolutely love?

9. What’s one similarity between us that you absolutely love?

10. A way to win your heart?

11.If you could turn any activity into an Olympic sport, what would you have

a good chance at winning a medal for?

12. What could you give a 40-minute presentation on with absolutely no

preparation?

13. What was the best compliment you’ve received?

14. What is something you will NEVER do again?

15. Is it okay to sacrifice one life to save ten? If you said yes, would you

change the answer if the one life was a friend’s life and the ten were

strangers? If no, why not?

16. Who would you most like to sit next to on a 10 hour flight and why?

17. You have $100 to burn, all your friends are busy and you have the

whole day to yourself, what do you do?

18. What is something you’ve done that you wish you could undo?

19. What inscription do you want on your gravestone?

20. What is something that can’t be taught and can only be learned with

age?

21. If you could be born again and choose what nationality, gender, and

race to be, what would you choose? Why?

22. If you had to change your name, what would your new name be, and

why would you choose that name?

23. If you could know the absolute and total truth to one question, what

question would you ask?

24. What’s the most interesting thing you’ve read or seen this week?

25. If animals could talk, which would be the rudest?

26. If you were arrested with no explanation, what would your friends

and family assume you had done?

27. What would be the worst thing for the government to make illegal?

28. What’s invisible but you wish people could see?

29. If someone gave you enough money to start a business – no strings

attached – what kind of business would you want to start and why?

30. What’s something you want to do in the next year that you’ve never

done before?

31. Tell me three things that happened in the last week that you’re

thankful for.
32. What’s your favorite memory we’ve shared together? Gimme as

many details as possible

33. What makes you happy?

34. How do you best connect with others?

35. What are the five most important things on your bucket list?

36. If a genie granted you three wishes right now, what would you wish

for?

37. What’s your favorite family tradition?

38. Tell me your life story in four minutes, with as many deets as

possible.

39. What’s something I’ve done for you that you’re grateful for?

40. What do you want your legacy to be?

41. Where was your favorite place to go as a child and why did you love

it there?

42. What was the first thing you bought with your own money? How old

were you?

43. What are your favorite three topics to talk about?

44. What is your love language?

45. In what situations do you feel most comfortable sharing your

perspective?

46. Who’s someone you really admire?

47. How do you like to be comforted when you’re upset?

48. If you had $100,000 to give away to any cause, which cause would

you choose and why?

49. Where are the top three places you want to travel to someday, and

why?

50. What do you want your final words to be?

51. Have you ever broken someone’s heart?

52. Can a society exist without laws?

53. How do you feel about sharing your password with your partner?

54. When do you think a person is ready for marriage?

55. What would you do if your parents didn’t like your partner?

56. If you are in a bad mood, do you prefer to be left alone or have

someone to cheer you up?

57. What would you sacrifice your life for?

58. Who would you sacrifice your life for?

59. Do you think the future will be better than the present? Why?

60. What’s the most crucial thing for a healthy relationship?

61. If science makes it possible to predict which people will be more

likely to commit crimes, should the highest risk individuals be jailed or

killed before they can commit crimes?

62. Why are there so many people who are lonely?

63. Why is it so hard for people to make real connections when almost

everyone wants to make real connections?

64. What keeps you up at night?

65. What are some examples of outside behaviors that are symptoms of

inner emotional scars?

66. There are two types of people in this world. What are the two types?

67. If you could make one rule that everyone had to follow, what rule

would you make?

68. What annoys you most about the in-groups you are a part of?

69. What are the top three things you want to accomplish before you

die? How close are you to accomplishing them?

70. In your group of friends, what role do you play?

71. What song always puts you in a good mood?

72. When you are old, what do you think children will ask you to tell

stories about?

73. If your job gave you a surprise three day paid break to rest and

recuperate, what would you do with those three days?

74. What’s wrong but sounds right?

75. When was the last time you got to tell someone “I told you so.”?

76. If you could have an all-expenses paid trip to see any famous world

monument, which monument would you choose?

77. What’s the most addicted to a game you’ve ever been?

78. What’s the most depressing meal you’ve eaten?

79. What songs hit you with a wave of nostalgia every time you hear

them?

80. What’s the funniest thing you’ve done or had happened while your

mind was wandering?

81. If you were given five million dollars to open a small museum, what

kind of museum would you create?

82. Which of your vices or bad habits would be the hardest to give up?

83. When was the last time you slept more than nine hours?

84. What was your most recent lie?

85. What was the best thing that happened to you today?

86. What languages do you wish you could speak?

87. What’s something that everyone, absolutely everyone, in the entire

world can agree on?

88. What country is the strangest?

89. Who do you wish you could get back into contact with?

90. How do you make yourself sleep when you can’t seem to get to

sleep?

91. What’s the worst hairstyle you’ve ever had?

92. If you were given one thousand acres of land that you didn’t need to

pay taxes on but couldn’t sell, what would you do with it?

93. When was the last time you yelled at someone?

94. What’s the most awkward thing that happens to you on a regular

basis?

95. If you had to disappear and start a whole new life, what would you

want your new life to look like?

96. What movie or book do you know the most quotes from?

97. What inconsequential superpower would you like to have?

98. What qualities do all your friends have in common?

99. What fashion trend makes you cringe or laugh every time you see it?

100. If you had a HUD that showed three stats about any person you

looked at, what three stats would you want it to show?

101. What’s something that everyone agrees we should change, but

somehow it never changes?

102. What naps are the most satisfying?

103. What’s the funniest TV show you’ve ever seen?

104. What’s the most boring sport, and what would you do to make it

more exciting?

105. Do you like things to be carefully planned or do you prefer to just go

with the flow?

106. What did you believe for way too long as a child?

107. What big event do you think will happen soon that most people aren’t

expecting?

108. If you owned a restaurant, what kind of food would it serve?

109. What do a lot of people have very strong opinions about, even

though they know very little about it?

110. An epic feast is held in your honor, what’s on the table?

111. Would you want the ability to hear the thoughts of people near you if

you couldn’t turn the ability off?

112. When was the last time you stayed up through the entire night?

113. What was ruined because it became popular?

114. What topic could you spend hours talking about?

115. What’s the most physically painful thing you’ve ever experienced?

116. What’s the cutest thing you can imagine? Something so cute it’s

almost painful.

117. What do you think about when you hear the word “classy”?

118. What’s the best and worst thing about the country you are from?

119. What values are most important to you?

120. What’s something that I don’t know?

121. What profession doesn’t get enough credit or respect?

122. What weird potato chip flavor that doesn’t exist would you like to try?

123. How much do you think names affect the outcomes of people’s

lives?

124. What do you think you do better than 90% of people?

125. How much of your body would you cybernetically enhanced if you

could?
126. Where is the most uncomfortable place you have ever slept?

127. Which parent do you identify with the most?

128. What embarrasses you in front of other people?

129. If you had to choose one thing you were most passionate about,

what would it be and why?

130. If you could buy one material thing, and money was not an issue,

what would it be?

131. Which famous person would you like to be BFFs with?

132. Is there anything I can do that will make your heart rest easier? Your

life running smoother?

133. What do you love about yourself most?

134. What makes you feel unstoppable?

135. How do you see me?

136. If you could do anything for the rest of your life, what would that be?

137. What makes you feel super loved?

138. What do you want people to feel when they’re around you?

139. Do you usually follow your heart or your head?

140. What did your last relationship teach you?

141. If you were able to live to the age of 90 and retain either the mind or

body of a 30-year old for the last 60 years of your life, which would you

choose?
142. If you could wake up tomorrow having gained one quality or ability,

what would it be?

143. Is there something that you’ve dreamed of doing for a long time?

Why haven’t you done it?

144. If you knew that in one year you would die suddenly, would you

change anything about the way you are living now? Why?

145. What does friendship mean to you?

146. What roles do love and affection play in your life?

147. When did you last cry in front of another person? By yourself?

148. What, if anything, is too serious to be joked about?

149. If you were to die this evening with no opportunity to communicate

with anyone, what would you most regret not having told someone?

Why haven’t you told them yet?

150. Your house, containing everything you own, catches fire. After saving

your loved ones and pets, you have time to safely make a final dash to

save any one item. What would it be? Why?

151. Share a personal problem and ask your partner’s advice on how he

or she might handle it. Also, ask your partner to reflect back to you how

you seem to be feeling about the problem you have chosen.

152. Who do you trust?

153. What are five things you’re thankful for right now?

154. Describe your worst date ever?

155. Would you rather be a horse or a cow?

156. How many boyfriends (or girlfriends) have you had?

157. What are some small things that make your day better?

158. What's the hardest lesson you've ever had to learn?

159. What's the biggest lie you've ever told?