The art of conversation is changing. Sometimes we are so connected to our screens that we forget to “connect” with those around us. It’s time to change this.

Once in a while, it’s nice to sit down, relax, and just talk. But, chatting can quickly get boring when you stick to small talk. After all, there is only so much to say about the weather. Luckily, posing a couple of hypothetical questions can quickly turn a dull chat into an invigorating conversation.

Whether serious or silly, hypothetical questions are a great way to get an interesting conversation started. They create an open environment where people can share their inner thoughts and feelings. You get to know the person you are talking to better since these “What if…?” questions force you to think and use your imagination.

Save your small talk for the strangers you meet while in line at the supermarket. Try out these hypotheticals the next time you want to have a real conversation.

Hypothetical Questions

1. If you had the chance, would you want to be pain-free for the rest of your life?

2. Would you take a $70k/week job offer where you get paid to sit in a pitch-black room and do nothing for 20 hours a day?

3. What would I hear if I asked a group of people who know you for five adjectives to describe you?

4. Which place on the planet would you never want to live, and why?

5. Which famous person’s body would you take over if you were a zombie?

6. What would your first reaction be if I told you that you had failed?

7. Would you rather forget about yourself or forget about anyone else?

8. Will you be able to give up 30 years of your life in exchange for allowing a stranger to die?

9. Would you take something that removes your body’s need for sleep if it was given to you?

10. Would you rather have to say anything that comes to mind all the time or never have to say anything at all?

11. Which mask would you like if you had to wear one for the rest of your life?

12. What music would you prefer if you could just listen to one song for the rest of your life?

13. What show would you like if you had to be trapped in a TV show for a month? And who would you be if you were a character?

14. We can select a single color that our eyes can see before we are born. What color would you like to choose?

15. Every day, 12 new things arrive in your house, all of which begin with a letter you choose. Which letter would you pick?

16. What would you choose if you had the option of living for seventy years and being incredibly happy or living forever and being unhappy?

17. How would you handle a situation at work where you were asked to execute a task that went against your morals?

18. Would you like to be the President of the United States or the Head of State of a Monarchy? Where would you rule if you were a monarch?

19. What would you eat if you could only eat one food for the rest of your life?

20. Do you think you could persuade a coworker to see your point of view on a strategy’s direction? If that’s the case, how would you persuade them?

21. Which world would you rather live in: Harry Potter or Twilight?

22. Why do individuals believe there are a billion stars in the universe yet have to touch their nose if they are told they have wet paint on it?

23. What would you do if you could go back in time and learn something sooner, and how would it change things?

24. Would you rather live for another 80 years and never leave your house, or live for another 10 years and be free to go wherever you want?

25. Would you kill one innocent child to heal the world’s diseases forever?

26. Would you know what to do if you were on vacation and lost your passport?

27. Which sport would you choose if you could be a professional athlete in any?

28. What video game would you choose if you had to live for a year in the last one you played, and how would your life be different?

29. Which would you prefer if you had the option of ceasing to exist or wandering the world forever, unable to engage with anything?

30. You are offered a pill that increases your intelligence by 50% but also permanently removing your hair, including your brows. Do you dare to take it?

31. What would you do if you made a strong recommendation in a meeting, but your coworkers disagreed?

32. Would you wish to travel to the future and be present at your own funeral?

33. What rule would you impose if you were the world’s king or queen?

34. How would you react if you were required to accomplish a task that made you unhappy at work? How would you approach management about this?

35. What would you teach if you had no choice but to teach?

36. Would you be willing to have your left middle finger surgically removed if it meant you’d never get sick again?

37. Do you believe that if all land was connected, the world would be a better place?

38. Would you be willing to forego all of your first-world comforts in order to live in a third-world country and be content?

39. What would you say if you had to sum up your life in 15 words or less?

40. What would you do if you were alone at home late at night and heard footsteps in your apartment or house? Would you panic or stay calm?

41. Is it better to save a sibling or five strangers if a building is on fire?

42. If you were offered billions of dollars to be locked in a room for 50 minutes with a huge possibility that when you leave the room, you will either be 50 days or 50 years in the future. Would you do it? Why or why not?

43. Where would you like to live if you could relocate anywhere and yet make a decent living?

44. What historical figure would be the most terrifying ghost to encounter?

45. You recognize that making a mistake early in a project will cause you to miss the deadline. What would you do if you were in this situation?

46. Would your partner still want to be with you if they could read your mind?

47. What crazy dictator things would you do if you were the dictator of a small country?

48. What would you do if you were working on a long-term project that had to be finished by the end of the quarter?

49. What do you think will happen if there were no seasons at all?

50. What would you do if you knew you’d go blind in three months? Is there something, in particular, you’d like to see?

51. What would you do if you could improve one aspect of yourself but had to reduce another by the same amount?

52. When you notice an endangered animal eating an endangered plant, what do you do?

53. A building is about to collapse and your mother and a sibling are inside the building. Your best friend‘s two newborn twins are also inside the building. Which pair are you going to save if you can only choose one?

54. Which would you prefer: a great love relationship that lasts a year or a mediocre relationship that lasts your entire life?

55. What three items would you take if you were shipwrecked on a desert island?

56. Which social media platform would you choose to own, and what would you change about it if you could?

57. Where would you live, what would you do, and how would you live if money were not an issue?

58. You’re walking through the woods when you come across a black suitcase. It contains a million dollars and a bloodstained piece of paper with the word “don’t” written on it. Will you take the suitcase home with you or leave it?

59. Imagine yourself with this business in five years; what do you want to be different about yourself then than you are now?

60. What strange thing would you make appropriate in society if you had the power?

61. What would be the first thing you’d do if time machines existed?

62. Would you visit Jurassic Park if it was real?

63. Hyenas seem to be constantly laughing. When they’re being killed, do they still laugh?

64. What would you ask your future self in the year 2050 if you could just ask one question?

65. Would you go three months without shaving, brushing your teeth, or using deodorant for $55,000?

66. Would you rather become more arrogant or more uneducated?

67. What would you do if a classmate asked you for the answer to a question during an exam when the teacher was not looking?

68. What would you choose if you had to choose between nighttime and daytime? What is the reason for this?

69. What would be the first rule you would make if you were the Emperor of the Earth?

70. What car would you turn into if you were a transformer?

71. Imagine you are hiking in the wilderness. You can swim across a mile-wide, ice-cold river in one day, or you can walk for an extra week to cross over the nearest bridge. Which would you choose?

72. How would you handle it if your friend resisted a new idea or policy you introduced?

73. How would the world be different if everyone were incapable of lying?

74. What meat would you like your sheets to be made of if they were to be made of deli meats?

75. Would you want to know if you were really a robot?

76. Do you want someone to tell you exactly what you’ll be doing in 20 years if you couldn’t do anything about your future?

77. If someone wanted to pay you $300K to spend one week in an abandoned house with one person without eating or sleeping, would you accept the offer?

78. If “I am” is said to be the shortest sentence in the English language, could it be that “I do” is the longest one?

79. If you could learn any skill you want in the world without trying, which one would you pick?

80. What would you tell someone if their underwear was showing?

81. What age would you prefer if you could go back in time and be any age you wanted for a month?

82. What dog breed would you be if you become one?

83. If extra lives were actually a thing in the real world, how would you be able to get them?

84. What would you sell your soul for if you could really sell it to the devil?

85. What animal would be much better if it were scaled?

86. You pick up a book and start reading, only to realize it’s your life. Do you turn the page knowing that you won’t be able to change the events that will unfold?

87. One day, you’re assigned to a large-scale project that has a direct impact on the company’s performance. What would you do if you were in this situation?

88. What would be the mission and who would be the members of your secret society if you could start one?

89. Imagine you are the emperor of a small island nation and can only choose five people from history to come and live on your island for three years. Who would they be and why?

90. Would you rather be bald for the rest of your life or get a massive mullet?

91. If you were given $1 million to spend on but going to die in ten days, what and where would you spend it on?

92. If you could erase one thing from the world, along with all of its memory, what would you erase?

93. If a turtle does not have any shell, is he considered homeless or naked?

94. How would you dispose of a corpse if a personal friend killed someone for a legitimate cause and you couldn’t report it to the authorities?

95. What would you say if the world is actually listening?

96. Which part of your body would you eat if you had to eat one part of your body or die a horrific death?

97. If you have complete freedom to select someone and every location on the planet, what would your ideal first date be like, and who would you go on it with?

98. What would your ideal planet look like if you could design it?

99. What would you do in the evolution of the human body if you could?

100. What would you do if a coworker took a long time to respond with the details you need to finish your task?

101. What would your aims be if you found an activist party, and what would you call it?

102. What would your superhero name be if you didn’t have any superpowers?

103. Which company would you choose if you could be the CEO of any company?

104. Does it still make a sound if a tree falls in the forest and no one is around to hear it?

105. What would your life be like if you had a 300-year life expectancy?

106. What musical instrument would you like if you could pick up any and play it beautifully?

107. What would you choose if you had to choose between Winter, Autumn, Spring, or Summer for the rest of your life?

108. Which one would you rather end: all wars or world hunger?

109. Would you leave your name and address if your car bumped with another car and no one witnessed it?

110. Which of your friends would you choose as your sidekick if you were a superhero? And what will your individual superpowers be?

111. What would you say first if someone took your VR headset off your head after you died and asked how your virtual life went?

112. Which of the two animals’ sounds would you like to swap?

113. Which band would you like if you could just listen to one for the rest of your life?

114. Will you speak up or keep silent if you are dissatisfied with your job?

115. If you could live in anyone’s head for an hour, who would you choose and why?

116. What would your name be if you were a celebrity for a day?

117. What would you wear if you could only wear one piece of clothing for the rest of your life?

118. What would you prefer if you had a year’s worth of free, unlimited services from a chef, masseuse, or chauffeur?

119. What would you do if you had the power to make one thing illegal and one thing legal?

120. Is it a hostage situation if an individual with multiple personalities tries to kill himself?

121. Which two limbs would you prefer if you had to lose one?

122. What would you ask God if you could just ask him one question?

123. Would you prefer to have four legs or four arms?

124. What mystery would you prefer if you could solve some unsolved mysteries in history right now, and why?

125. Would you snap your fingers if every time you did, you were immediately transported to a different point in humanity’s timeline? If that’s the case, how often do you do it?

126. Would you rather spend the rest of your life traveling to only one city or never leaving your home state?

127. What would I learn about you if I had the opportunity to speak with someone who disliked you?

128. What holiday would you make if you had the power to do so, and what month would it fall on the calendar?

129. What would be your dream last meal? What’s on the dinner menu this time?

130. What would you do if a zombie apocalypse started right now?

131. What would you choose if you had to choose between a great friendship and an average relationship?

132. What animal would you like if you could shrink any animal to the size of a chihuahua?

133. Do you think you’d be able to pull a sock out of your mouth without using your hands or feet?

134. Which would you prefer: living in a tropical island resort for the rest of your life with three friends and never having to leave or living a regular life in the suburbs?

135. Which bird would you prefer if you could be any bird?

136. Would you rather learn a lot about a little or a little about a lot?

137. What would you like as the subject of an in-depth documentary if you had the opportunity?

138. What would you smell if you were constantly surrounded by one aroma, aside from your normal scent, that you and everyone else could smell?

139. Which two species would you choose if you could create a hybrid animal out of any two?

140. What would the sign on your door say if you were a consultant?

141. What would you say in one last text message to everyone on the planet?

142. What kind of dinosaurs would you clone if dinosaurs could be brought back to life?

143. Would you dare to give up true love for a million dollars?

144. Would you want to know if it turned out you were in a coma and your whole life had been a dream?

145. If you could be invisible but fart loudly every 30 seconds, how would you use that?

146. Why are there phone bills in a country of free speech?

147. Would you kill an animal for every piece of meat you ate?

148. Which plant would you like to be if you could be any?

149. You are driving alone in your car on a wild, stormy night, as it is raining heavily. Suddenly, you pass by a bus stop, and you see three people waiting for a bus, what would you do?

150. What would be the best choice for Planet Earth to showcase if it were in a science fair with other planets from all over the Universe?

151. Which color would you like to survive if humans lost their ability to see all colors except one?

152. What amount of money per month will you need to give up your cell phone for good?

153. Who would you want as a mentor if you had the opportunity, and why?

154. Who would you pick as a friend if you could choose anybody in the world?

155. Who would play the lead role in your life if it were a sitcom?

156. Would going out to eat or to see a movie by yourself make you feel uncomfortable?

157. Will it be considered a walk if you removed the wings of a fly?

158. Imagine waking up as a performer for a medieval king’s court. What would you do to entertain him?

159. Would you rather be a hidden dragon or a crouching tiger?

160. Would you rather be completely nude for the rest of your life or wear only underwear?

161. What language would you like to learn if you could speak some other language besides English?

162. Will you accept the opportunity to visit an alien planet if it meant being frozen for 20 years while the spaceship traveled there?

163. What would be your conspiracy theory if someone had one made up for them?

164. Which animal would you prefer if you could give wings to any species?

165. Which one would you rather be: an astronaut or a deep-sea diver?

166. What questions would you ask if you were the interviewer instead of the interviewee of a certain company?

167. Who would you call on the phone if you were about to be killed and could only say goodbye to one person? And what would you say to him or her?

168. Where would you like to live if someone left you a cottage in the countryside in their will?

169. What would you replace burping sounds with if you could replace the sounds your body makes with something else?

170. How do you think you might have responded to the question, “Where do you see yourself in 5 years?” five years ago? Are you satisfied with the changes if you aren’t where you are now?