Open-ended questions are the best for getting to know someone. They can range from relatively harmless ones like funny stories to the weird and awesome like how to get out of being imprisoned forever.
Below, we’ve compiled a huge assortment of questions you can ask to get to know someone better. But let us warn you that these questions might open up someone’s deepest, darkest desires. So unless you’re ready for that, reconsider opening this can of worms!
Cute little anecdotes that give you a glimpse into someone’s childhood – from the strange to the hilarious.
1. What is your most embarrassing moment when you were in school?
2. What is the dumbest thing you ever said out loud?
3. What is the silliest thing you believed as a child?
4. Who was your childhood best friend and how did you become such good friends?
5. What adventures did you have with your childhood best friend?
6. Who was your childhood hero and what did you like the most about them
7. What was your secret base with your friends and what sort of fun activities did you do there?
8. Who was your worst enemy in grade school and how did you overcome it?
9. Were you the one bullied or the one who bullied? Why?
10. What was the best Halloween costume you ever had? Do you have photos of this?
11. What was the best field trip you went on and what silly stories do you have about those trips?
12. Who was your favorite teacher in grade school and why did you like this teacher?
13. What is your funniest story about your siblings?
14. Have you ever gotten into trouble when you were a kid? What did your parents say?
15. What was the thing that scared you the most as a kid and why?
16. What was your favorite game to play? Were you any good at it?
17. Can you remember all the friends you had when you were a kid?
18. Have you ever gotten into kitchen mishaps when you were a kid?
19. What TV show or movie did you always want to watch when you were younger?
20. What was your most memorable camping experience?
21. What was the scariest ghost story you ever heard as a child?
22. What was your town’s most famous urban legend? Did you prove it to be true?
23. What was your happiest memory with your family?
24. What was the best thing that ever happened to you in school?
25. Who was your childhood sweetheart?
Love Life Tales
When you like someone, you want to know about what they’re like when they’re in a relationship, right? These are the questions to ask!
26. Who was your very first crush and what did you like about him/her?
27. What did you do to try to tell your crush you had a crush on them?
28. Has anyone ever had a crush on you when you were younger? What did you do when you found out?
29. What was the silliest thing you ever did to make your crush notice you?
30. Who was the kid that everyone had a crush on back when you were younger? Did you like them too? Why or why not?
32. What is the most embarrassing thing you ever did in front of your crush?
33. Who did you have a crush on when you were in high school or college?
34. Have you ever had a crush on your teacher?
35. What is the funniest story you have about trying to impress someone?
36. What is your go-to no-fail pickup line?
37. What is the dumbest pickup line you’ve ever heard?
38. What is the smoothest pickup line you ever heard?
39. Was there ever a time when you were completely oblivious to the fact that someone liked you?
40. Which of your friends had the smoothest moves when it came to attracting people they like?
41. Where did you go on your first real date?
42. What was your puppy love story?
42. When did you realize you were finally in love with someone?
43. What did someone do to make you fall in love with them?
44. Who is your craziest ex? What did they do to make you think they were crazy?
45. Which of your exes do you think still has a thing for you?
46. Have you ever had to “fight” for a relationship?
47. What is the dumbest thing you ever fought about with a significant other?
48. What is your experience with long distance relationships?
49. Have any of your significant others ever said something so out of touch with reality that you started to question their sanity?
50. If you could take back dating someone from your past, who would it be and why?
These are just getting-to-know you questions that may reveal things about your crush that you wouldn’t otherwise learn.
51. Who do you think is the most attractive woman in the world?
52. Who do you think is the most attractive man in the world?
53. If you could borrow a singer’s voice for an entire day, whose voice would you borrow?
54. If you could have an artist’s skill for one day, what would you paint?
55. What superpower do you want to have?
56. Would you prefer a weekend getaway at the beach or a staycation in a fancy hotel?
57. What movie can you watch over and over and over again?
58. What TV show or movie do you regret watching and wish was never made?
59. After a hearty dinner, do you want ice cream or cake?
60. How do you like your coffee?
61. What kind of pet do you want to have?
62. What do you think is the most well-made electronic device?
63. What skill do you wish you could master?
64. Would you prefer to go to a freezing cold country or one that is hot and humid?
65. Do you want a small, cozy house in the city or a big, spacious one in the suburbs?
66. Would you rather write a book, act in a play, or draw a landscape?
67. When it comes to desserts, do you want it rich and chocolatey or light and fruity?
68. Would you rather cook a full-course meal or clean the entire house?
69. Would you rather eat something extremely spicy or extremely sour?
70. Would you rather listen to your favorite album over and over again or a playlist with random songs that never repeat?
71. Would you rather wear formal leather shoes or socks with sandals?
72. What is the worst fashion crime a person could ever commit?
73. What is your worst pet peeve?
74. Would you rather socialize at a big party or spend hours alone with a book?
75. Would you rather take a long drive to a scenic spot or take public transport to a busy and bustling city?
76. Would you rather have the worst hangover in your entire life for just one day or continuously stub your toe against furniture three times a day for three days?
77. Would you rather play at the swings or the monkey bars?
78. Would you rather babysit 5 sleepy toddlers or three rebellious teenagers?
79. What is the worst chore that you want your worst enemy to do?
80. What is one thing you can’t leave the house without?
81. Would you rather eat raw fish or unripe fruit?
82. What is the weirdest food you actually want to try?
83. Would you rather live in a fancy high-rise condo or in a cozy little cabin in the middle of the woods?
84. If you could have one director create the movie of your life, which director would you choose?
85. Which actor do you think should play you in a movie?
86. If there was one artist or band who would play the soundtrack of your life, who would it be?
87. If you could have only one condiment for the rest of your life, would you choose ketchup or mayonnaise?
88. Which country do you think has the best food?
89. Which historical figure would you like to interview to clear up some false history facts?
90. Which Disney princess do you think would win in a fistfight?
91. Who is the most menacing villain on TV?
92. Which superhero do you want on your side when you get into a fight?
93. Which superhero do you think has the weirdest backstory and why?
94. Which superhero do you not want to get into an argument with?
95. Would you rather have Superman sucker punch you in the gut for a million dollars or have Batman kick your shin for a thousand dollars?
96. Which of the Greek gods do you want to be your ultimate bestie?
97. Would you rather give up all carbs (rice, pasta, potatoes, sugar, etc.) or red meat for the rest of your life?
98. Which job do you think you’d be able to do better: a spokesperson for a small company or a computer technician?
99. Would you rather go skydiving or bungee jumping?
100. What scary stunt will you never ever try?
101. What’s the most thrilling thing you could ever do?
102. Would you rather have a job that requires you to sit for 8 hours straight or a job that requires you to stand for just four hours straight?
103. What is your most comfortable pair of shoes?
104. What is your ultimate go-to outfit for a special event in your life?
105. Who do you think is the smartest living person and what would you ask them?
106. What would you ask an oracle if you met one?
107. What’s worse being stuck in traffic that goes on for miles while you have explosive diarrhea or wading through a bunch of trash looking for something you accidentally threw out?
108. What’s the creepiest looking building you’ve ever seen?
109. If paranormal entities were real, which of them do you think you could actually be friends with?
110. Which would you prefer: a TV that can only ever play shows from 3 channels or a TV with all the channels but they’re all in black and white?
111. If you could declare one person to be the President of the United States for a single day, which one would you choose to create the most chaos?
112. What do you think is the most useless invention in the entire world?
113. What diet do you think is actually a conspiracy by the government?
114. What conspiracy is so outrageous it might actually be true?
115. What is the best website or app to get on when you’re bored?
Now on to the fun stuff! Here are all the weird and wonderful questions to have a long-winding conversation!
116. You have a million dollars that you have to spend in under 5 minutes. What do you buy?
117. You have a million dollars that you have to fish out of the sewer with no gear. Would you do it?
118. You can get a million dollars for eating a single Carolina Reaper pepper. Would you do it?
119. You get a million dollars for punching your best friend in the face. Would you do it?
120. You get to pick a fruit that you need to eat for a whole week with no other food. What fruit would you pick?
121. You’re stick in a desert island. However, you need to forego one of the following: a working toilet, electronics, or water. Which would you give up?
122. All the people you have ever dated suddenly appear in one room with you without knowing why they’re there. What would you say to each and every one of them?
123. You have a genie that will grant you one wish, but your significant other gets the complete opposite. What would you wish for to create the best deal for both of you?
124. You are about to die within one hour. What’s one thing you want to check off your bucket list?
125. You suddenly wake up in the body of the most influential person in your country. Without arousing suspicion from the people around you, what would you do to make your country a better place?
126. You have one week to learn a new language or be imprisoned for life. What media would you consume to accomplish this is the most efficient way possible?
127. You are taken hostage by terrorists. They will set you free after telling them a joke that would make all of them laugh. What joke would you tell to secure your freedom?
128. You have 24 hours to find a person who can answer any question asked about you. Who would you pick and why?
129. You have a gun to your head. You need to sing a song with complete lyrics or you will get shot. What song, aside from nursery rhymes, would you sing?
130. You suddenly have the power to erase one person from existence. Who would you erase?
131. You have a time machine that can take you back to any point in time. However, this time machine can only send you one way. Which time period would you go to?
132. You have the power to go back in time to a period before the industrial age (pre-1890s). You can go to any country or to any century you wish. What skill or piece of technology would you introduce to that civilization without getting them to kill you for being a sorcerer?
135. You have magical healing powers that can cure only one disease. Which disease would you choose and why?
136. A useless object is suddenly deemed precious and expensive. What useless object do you want it to be so you’ll become rich?
137. You can inhabit the body of any person in the world for just one day. Which person do you want to possess and what would you do within that timeframe?
138. You are suddenly the ruler of an entire nation with a population of one million people. This nation is not rich, but there are no corrupt people in your retinue. What would you do with your reign to ensure that your country bests all the other rich countries in the world?
139. You have to invest all your money into something, but you only have one minute and no internet to think about it. What would you invest in and why?
140. You suddenly have the power to speak to all domesticated animals. What message would you tell them?
141. You get to choose a skill you can be the best at. However, instead of you actually getting better at it, everyone just gets worse. What skill would you choose?
142. You get the ability to become immortal as long as you never allow another person to touch you. Would you do it?
143. Someone will give one dollar for every day you don’t interact with another human. That includes social media, phone calls, or even making eye contact from across a room. How many dollars do you think you could make?
145. You become the proud owner of a worldwide business that allows people to erase certain parts of their memory, such as in The Eternal Sunshine of the Spotless Mind. What’s the one memory you would never allow anyone to erase?
146. One inanimate object will disappear from the world forever and never come back. What object do you want it to be?
145. If you could clear up one huge historical or scientific misconception once and for all, what would it be?
146. What would you do if the Queen of England suddenly knocked on your door and told you that she would be staying at your place for one week?
147. You are a chef at a fancy restaurant in the richest part of New York. A country bumpkin who just won the lottery walks in through the door and asks for a personalized meal from you. What meal would you prepare to make him feel at home and fancy at the same time?
148. If you woke up to find that you were still 15 years old and was just dreaming of what adult life is like, what is the first thing you would do?
149. You are on your first date with someone you’ve had a crush on for years. Who is the one person you wish would come up to you and casually say hello like they’re your oldest pal?
150. You are a mystic divorce lawyer who can immediately see through a couple’s lies. You are tasked to pick out one couple that’s sure to divorce so that you can reveal what they’ve been doing all along. Which celebrity or high-profile couple would you chose to out?
151. You are cursed to eat only one type of food for the rest of your life. Luckily, you get to choose what type of food. What would you choose?
152. You are granted an extremely mundane superpower that can neither grant you strength, power, or money – like the ability to help grass grow just a little faster or to change water’s temperature by a few degrees. What superpower would you take?
153. You are having a conversation with the god of death. He asks what fatal thing you want to turn into something non-fatal. Like a gunshot wound or internal bleeding becoming suddenly non-fatal. What would you choose?
154. You can speed up or slow down the time one minute at a time. What part of your day would you like to speed up or slow down?
155. You meet a vampire who has been alive for a thousand years. What’s one thing you would ask?
156. You are able to communicate with one type of animal for 24 hours. What animal do you want to communicate with?
157. You are granted access to the confidential files of the FBI to find the truth about one thing. What FBI dossier would you like to take a peek at.
158. You meet an alien with an advanced mind and technology. He asks you for one thing that would describe the entire human race, but you only have 5 minutes to explain it to him. What artifact would you present to the alien?
159. If you could be the world’s best undercover detective for a span of 3 days, who would you investigate and why?
160. You get one opportunity to teach all parents a valuable parenting technique. What would you teach them that could change an entire generation of children?
161. If you could change your name into something else, what name would you pick?
162. You have inevitably messed up big time at work, and have 24 hours to come up with an alibi. Which friend would be able to give you that alibi?
163. You are suddenly the CEO of McDonald’s. What item would you add to the menu?
164. You find an abandoned house that’s fully furnished with modern technology, but clearly no one has been there for years. What do you do?
165. You suddenly find that your bank has tripled your bank account balance. Are you suddenly rich or did you just gain a couple of dollars?
166. You are engaged in a non-swearing insult contest with the person you hate the most in the world. What is your most creative insult that’s sure to make you win?
167. You need to make a bunch of preschoolers laugh with just one joke. What joke do you go with?
168. You have one hour to create an awesome meal fit for Gordon Ramsay from the items you have in your kitchen. What creative insults do you imagine would come your way?
169. If there was one band you could immediately disband to bar them from ever attempting to make music again, what band would it be?
170. You are the smartest person in a group of survivors on a deserted island. How bad are things going to get?
171. Are you willing to lose one ability to supercharge another?
172. What’s the first thing you would say to an alien who’s curious about humanity?
173. You have unlimited money for a one-week vacation. Where would you go?
174. You have unlimited money to spend on a trip to the dollar store, but you can only fill one cart. What do you get?
175. You can read the mind of only one person. Whose mind would you choose to read?
176. You switch bodies with your pet cat who loves to wander outside. What cat adventures would you go on?
177. Your phone is suddenly hacked and people keep calling you to ask for love advice. What advice would you give?
178. You find out you have an identical twin who is the exact opposite of you. Would you dare to meet up?
179. Your parents confess that you were secretly born to lead the nation into a war against supernatural beings. Who would you turn to for advice?
180. Death is literally knocking on your door. What do you say to buy yourself some time?
Don’t you wish you could answer all these questions yourself too?