Real-time conversations have become increasingly rare in the world of the internet, where everything can be accessed in a matter of seconds.
Even while meeting face-to-face, people are found on their phones chatting online. Asking hypothetical questions can add a lot of flavors and spark to your conversation.
You’re free to ask any kind of hypothetical question, whether funny, romantic, personal, or stupid.
This type of question is a great way to begin a meaningful and entertaining conversation. Asking a What If or a situational question requires imagination and is a great way to initiate a conversation with loved ones or a new acquaintance.
Summary in Infographics
What are Hypothetical Questions?
Hypothetical questions are based on assumptions, not facts. The one who asks the questions sets the parameters and conditions for the participants.
Hypothetical questions are used to stimulate discussion and elicit opinions. Rather than being based on facts, the question is based on an imagined scenario. Hypothetical questions are asked on the basis of events or the possibility of happening an event.
It allows the respondent to imagine the scenario and think about how well they respond to certain situations in life when confronted. Whoever asks the questions sets the parameters and conditions for respondents.
Funny Hypothetical Questions
Asking personal and romantic questions are good but adding a pinch of humor into the conversation is a great way to add happiness and make people laugh.
1. Is there a purpose to driving on parkways and parking in driveways?
2. If a fly doesn’t have wings, would it be considered a walk?
3. It’s not clear why there aren’t B batteries
4. How would you react if God sneezes?
5. What if a child doesn’t sleep during nap time? Are they guilty of resisting rest?
6. When a group of cats jumps on each other, is it still called a dog pile?
7. If you were told that there were 1 billion stars in the universe, you would believe them, but if you were told there was wet paint on a wall, you would have to touch it to be sure?
8. Are you interested in visiting Jurassic Park if it were real?
9. Which pirate name would you choose if you were one?
10. In your opinion, which tree type would you be, and why?
11. If you could have a drink at a fictional bar, where would you choose to go?
12. Do you have a fantasy creature you’d like to see come to life?
13. Who would you pick if you had to have sex with a cartoon character
15. Which animal would be the cutest if it was the size of a hamster?
16. Imagine you are the opposite sex for a day. How do you spend your time?
17. In the case of transformer reincarnation, what type of vehicle would you become?
18. As a vampire, how would you style your hair if you did not have a reflection?
19. What would you change about an embarrassing moment if you could go back in time?
20. Are you reincarnated into an animal with a personality similar to yours? What species are you?
21. If every time you entered a room, you had entrance music. What song would you pick?
22. You’re a mad scientist. Which experiment would you conduct if money and ethics weren’t a factor?
23. If you could make a fragrance of your own, what scent would you choose? What name would you give it?
24. Which of the seven dwarves would you be? Are you sleepy, grumpier, happier, sneezy, dopey, bashful, or doggone?
25. What would you buy your girlfriend as an apology if she were a florist and chocolate did not exist?
26. There you are, out with a bunch of people and the discussion bores you. How would you change it?
27. A witches’ spell has turned you into an inanimate, non-electric object. You have been turned into a non-electric inanimate object by a witch’s spell. If you needed a hundred people to touch you to break the spell, what would you be?
28. There are three celebrities you can kiss, one to marry, and one to murder. Who are they?
29. Would you replace burping sounds with another sound if you could change the sounds your body makes?
30. Is it possible to tell whether it is partly cloudy or partly sunny?
31. If you had to wear a mask for the rest of your life, what type of mask would you choose?
32. Could you imagine yourself as one of these animated characters, and which would it be?
33. If you were offered a pill that would enhance your intelligence while also taking off all your hair, would you take it?
34. How would you design an abomination if you were responsible for product development for a large fast-food chain?
35. How will you gain the trust of animals if you know they are plotting against you? Which animal would be your first choice?
37. In a scenario where you had to be haunted by a ghost for the rest of your life, which one would you choose?
38. What causes our feet to smell and our noses to run?
39. If you have to choose an animal one of the size of a chihuahua, which animal would like to choose?
40. Would you use the ability to be invisible but fart loudly every few minutes in some way?
41. If zombies were to affect human civilization, what weapon would you choose?
42. Imagine that you are a superhero, who would be your sidekick, and what powers will you choose to have?
43. What would a prison planet look like for crooked politicians if you could design it?
44.. Who do you think would be the first animal to fly if wings were attached to it?
45. What design would you choose for a full-body tattoo if you were forced to get it by law?
Good Hypothetical Questions
You can add some amazing imaginary questions to your conversation with some good hypothetical questions to make your conversation lighter and more engaging.
46. What would the world be like if the land was all connected?
47. Is it possible for you to survive if food shipments completely ceased?
48. What skill would you learn instantly if you could choose any in the world?
49. What if you had the possibility of raising one aspect of yourself (beauty, intelligence, confidence) but had to lower another aspect despite the same degree?
50. You are offered $1 million by a distant relative if you can use up $100K in one week. When you can’t donate or spend the money all at once, how would you spend it?
51. Which major corporation would you choose to run if you were CEO for a year and what changes would you initiate?
52. Which age would you choose to go back to if you could go back in time for a month?
53. What would you do differently if you could start this year over?
54. How would you spend your first day as president if you were to be elected?
55. Which name would you use for your bar or coffee shop, and how would it stand out from other competitors?
56. It’s Comic-Con, and you have a cosplay that looks so real, you freak everyone out. What do people call you?
Hypothetical Interview Questions
Hypothetical questions are commonly asked in job interviews. You may use them while interviewing someone or while preparing for the one. Also, you can practice these questions to sharpen your answering skills. It’s a great way to learn something new and valuable.
57. What would be your reaction if your boss informed you that you failed?
58. When you are a leader of a team, what would you do to boost morale if the team members are feeling low?
59. Which professional would you like to be mentored by and why?
60. How would you react if you discovered that a colleague was stealing office stationery?
61. You disagree with your boss’s decision. In such a situation, what would you do?
62. Can you imagine what would happen if you found out that your manager was hiding information from you?
63. You are working with a team, and there are frequent arguments between two team members. How would you react?
64. What would be your reaction if an unhappy customer calls and behaves aggressively towards you. In what way do you react?
65. You’ve been with this company for three years, what will be different about you next year compared to now?
66. Imagine it’s a bad day and you have a tight deadline looming. A colleague has been late three times this week. How would you react?
67. There’s a disagreement at work over project direction. Can you tell me how you would persuade them?
68. You have an idea you think will work. In spite of your enthusiasm, your team declines the idea. How would you react?
69. The colleague you work with is taking a long week. And they tell you that they plan to take the day off, calling it a sick day. What would you do and why?
70. A mistake in your work goes unnoticed by others. Are you willing to address the problem even if it slows down the project, or do you prefer to ignore it to move forward?
Best Hypothetical Questions
The best hypothetical questions will elevate your conversation by giving you a small push to get your thoughts going and by allowing you to get to know your companion better.
71. Which subject would you teach if you become a high school teacher?
72. If you have the power to choose your age and could stay that age forever. What would you choose?
73. What would you prefer to do if you were on death row but you could choose any execution method as long as it was quick?
74. If you had full knowledge of any five things, what would it be?
75. Do you prefer to know a lot about little or a little about a lot?
76. What would you dream about tonight if you were the one in charge of your dreams?
77. What would you do if you had the power to increase your lifespan by twenty years by leaving a stranger to die?
78. Which name and identity would you choose if you were a WWE wrestler?
79. Are you willing to risk your life to save a stranger’s life?
80. What disaster would you choose to face if you had to face a massive natural disaster?
81. If you could only own one luxury item that you could never sell, what would it be?
82. If you could choose your gender, which would you choose?
83. Suppose you went deaf, what would be the one sound you would miss most?
84. In your ideal world, where would you like to live?
85. How would you change the country if you were president today?
86. One last time, if you could only say something to one person, what would it be and to whom?
87. Can humans defeat aliens?
88. What question would you ask from your future self from 2040?
89. Do you think you would accept $100K to spend one week without food or sleep in a dark room – with one other person?
90. Every day, you see ten new things in your backyard. Which letter would you prefer if all of them began with the same one?
91. Which city would you live in and what would you do if you were guaranteed a living wage?
92. What is the first thing you would say to your parents if you could time travel and meet them before they were born?
93. What would happen to the world if people couldn’t lie?
94. If you had the power to erase one thing from existence forever along with all your memories of it, what would you pick?
95. What musical instrument would you prefer to play beautifully if you could choose anyone?
96. If you could make one thing legal and one thing illegal, what would you do?
97. If you could take a sci-fi novel or movie and turn it into a reality, what would it look like?
98. Imagine having your own reality TV show. Then how would it feel?
99. What show or event would you attend if you could have tickets for you and as many guests as you like?
100. In a perfect world, what would you do differently and how would it change things?
101. What would you choose if you could have a chef, a housekeeper, or a chauffeur for a year?
102. If you knew you’d be happy in a third-world country, would you give up your first-world perks?
103. What if something were offered to you which would erase your body’s need for sleep?
104. If you lived to 500 years old, how would your life be different?
105 What would you say if you could send yourself a ten-second message from ten years ago?
106. Is there anything you would do differently if you knew no one would judge you?
Hypothetical Relationship Questions
When your relationship lacks that spark or newness, then you can add some spice to your conversation and engage in a wonderful discussion. If you ask your partner these hypothetical questions, you will learn a little more about them and discover new things about each other.
107. Think about how much you love your partner but the sex isn’t enough for you. Would you mind telling them?
108. Think about what could happen if you cheated on your partner. Afterward, you felt extremely terrible and were sure you would never do it again. Do you think you would confess your secret to your partner anyhow?
109. Think about the scenario where you fall in love with your partner’s best friend. How would you break it to them?
110. Think about what it’s like to have sex with your partner. You accidentally call them by another name. What would you do to fix things?
111. Suppose your partner had murdered someone. What would you do if they were going to be put behind bars?
112. Would you go to jail if you had the option to so that your partner could continue living their lives?
113. When you have a very busy schedule, how do you manage your sexual life?
114. If you could save your partner’s life by killing ten innocent people, would you do it?
Flirty Hypothetical Questions
Do you want to learn more about that person that you are dating? By using these flirty hypothetical questions, you can get to know your date better and have fun too.
115. Would you pick me up if I called you late at night?
116. What is your favorite song to dedicate to your loved ones, and why?
117. Which are 3 things that you’d do if you had all the time and money in the world?
118. If you loved someone, but they didn’t like you back, what would you do?
119. What would you rather have, finding your beloved or becoming a millionaire?
120. If you had to choose between pulling your hair and smacking your butt, which would you prefer?
121. What would you prefer to receive as a good-bye text or a good-night text?
122. How would you prefer to be said goodbye through a kiss or leaving you to sleep?
123. Imagine going to the shower with your boy crush from high school. What would you do?
124. Would you rather grant romantic wishes yourself or be granted them by someone else?
Crazy Hypothetical Questions
Being crazy gives you an opportunity to demonstrate a side of your personality that you may not normally exhibit. Ask questions to uncover it.
125. During the zombie apocalypse, you can choose three companions. What would be their occupations?
126. What if you became invisible for a day. Where would you like to go?
127. If you were given the opportunity, would you go cryogenically frozen?
128. If you could bring back one person to life, who would it be?
129. What would you teach your pet if it could speak? Which phrase would you like to see it say?
130. If you were in prison, would you focus on exercising or reading books?
131. What TV show would you pick if you had to live there for one week?
132. Which item would you stockpile if you found out they were going to stop selling it?
133. How would you wield your power as a superhero?
134. What kind of power would you invent that no superhero has ever used?
135. You have gone missing and now your family and friends realize that you have joined a cult. What kind of cult is it?
136. It’s 1500 and you don’t own anything and are without clothes. What do you do to prove you’re from the future?
137. What eccentricities would you indulge in if you were wealthy beyond your wildest dreams?
138. You’re standing outside of a bank when an armed robber runs past. To keep you quiet, he gives you $10,000. It won’t affect you. Would you like to keep it?
Hypothetical Questions for Couples
Bring some spark to your conversation by asking thoughtful and intriguing questions to your partner. These hypothetical questions are specifically framed for couples to ignite fun and a lively discussion.
139. Are you interested in getting married in the future?
140. If you were to rate your kissing skills, how would you rate them?
141. In your opinion, what is the key to a happy marriage?
142. How many times do you have sex each week?
143. Are you planning on having children? If so, how many would you like?
144. What do you think about roleplaying?
145. Do you think physical chemistry matters in a relationship? If so, what is your opinion of it?
146. Do you intend to raise your kids religiously?
147. What is the best way to discipline a child?
148. What kind of environment do you want for your family? Urban or rural?
149. How good is the sex? Rate it from one to ten.
150. Imagine you had sex with your partner’s sibling. How would you handle the situation?
151. Imagine your parents walk in on you while you’re having sex with your partner. What would you do? How would you tell them?
152. The night before your wedding, you learn your partner is cheating on you. How would you react?
153. Assume that you told your partner you would stay indoors and then crashed into them at a party. How would you react?
154. If you and your partner are on vacation, and their sister surprises you. What would you do?
155. If you drunk call your ex and he hears the entire conversation, your current partner will certainly hear everything. What do you do about the mess?
156. If you could go back in time, you might be able to meet your partner again. How would you do things differently?
157. You have the power to change anything about your partner. Then, what would it be?
158. Consider the possibility that you and your partner are married. You’re robbed one day, and you lose all your money. Do you still want to be together?
159. Which social media app of your partner would you use if you could access it without them knowing?
160. How would you spend the day if you could trade places with your partner?
161. Who would you permanently remove from your partner’s life if you could and why?
162. If your celebrity crush asked you out, would you dump your partner?
163. What if someone offered you Rs 100 crore? Would you break up with your partner?
164. Will you still be with that partner if he/she were unable to have sex with you due to some medical condition?
165. What if your partner gets amnesia? Would you still be with them if they let you go?
166. If your partner were allergic to your pet, would you give it up for them?
167. Imagine you and your partner were stranded on a deserted island together with a single slice of pizza remaining. Would you give it to them or eat it secretly?
168. Imagine you were given superpowers and swore to keep them secret from everyone. Would you still tell your partner about it?
169. What if you could read your partner’s mind without their consent?
170. What would you do if your partner begged you to get a strange tattoo of their face on your arm?
171. What would you do if your partner had the chance to kiss their favorite singer? Will you give the concert pass to him/her?
Weird Hypothetical Questions
Weird things happen to everyone, so here are some weird questions to uncover the weirdness within your conversation partner.
172. If you could normalize anything weird, what would you do?
173. If you discovered that you were actually a hybrid of humans and aliens, what abilities would you like to have?
174. What would you want to be associated with if everyone knew you by a particular scent?
175. What would you do first if you suddenly found yourself homeless, broke, but invisible?
176. If you could cook one meal flawlessly, and everything else was garbage, what one meal would you pick?
177. Having won the lottery, you will be able to eat whatever you want for the rest of your life. What is it?
178. What kind of monster would you want to be if you had to be one night a month?
179. How would you describe yourself if you were a food?
180. What would you do if you woke up one morning with wings?
181 What would you like to see growing on trees?
182. Your roommate hung a giant U.S. flag on the wall that occupies the most space in the living room. What will you do?
183. Which two limbs would you rather lose if you had to lose two?
184. If you could choose any historical figure to haunt a current world leader, who would you choose?
185. Who would you listen to as a constant companion throughout your entire life?
186. If someone paid you a certain amount each month to give up your mobile phone, would you give it up?
187. Would you force the marriage of a princess of one kingdom to the prince of another’s stop a disastrous war between kingdoms?
188. Would you change how you live your life if you could re-spawn at home after dying (like in a video game)?
189. As you read your favorite sci-fi movie or novel, how much better would the world be if technology were as it was 200 years ago?
190. Do you think that you’d stitch something together by hand if you didn’t have a sewing machine, or do you think you’d wear a robe made from curtains?
Dumb Hypothetical Questions
Dumb questions are the best because they don’t need to be logical. Also, it doesn’t require much thought. It is all about having fun and laughing out loud.
191. Are you more interested in being ugly or dumb?
192. If everyone on Earth jumped at once, what would happen?
193. What part of a car would you be if you were one?
194. What would you rather plunge into, a swimming pool full of piranhas, or a shark-filled pool?
195. Imagine if there were no women in the world for 24 hours. How would you react?
196. Would you rather talk all the time or not at all?
197. A gun is held against you and you’re asked what is for not pulling the trigger. What will you say?
198. Earth has been taken over by aliens, and humans have been put in zoos. How would you like your zoo enclosure to look?
199. Humanity is at war with AI robots. It’s suspected that you’re a robot. What would you say if you had to prove that you are human?
Hypothetical Questions to Ask your Girlfriend
There is always room to get to know your partner better and to become closer. These Situation-Based questions will help you discover the deep-seated desires and thoughts of your girlfriend.
200. If you were turned into your boyfriend for a day, what would you do?
201. If you could give a nickname to your partner for one month. What would it be?
202. Would you be able to manage multiple boyfriends simultaneously?
203. If you had cheated on your partner and felt terrible about it and knew you wouldn’t do it again, would you confess?
204. Wouldn’t it be nice if you could relive one day in your life? Which one and why?
205. Could we still be together if we had only one day left? What should we do?
206. If you could read my mind, what would you do? How would you use it? Good or evil?
207. Would you break up with me if you were offered $10 million? Can you accept it? Is there a specific amount you would accept if not?
208. If we were stranded together on a desert island, what would we do?
Hypothetical Questions about Life
You can use these questions to let your mind wander and explore different topics about life and all that you have been curious about. Let your imagination run wild with these questions.
209. How would you obtain extra lives if they were real?
210. Would you live 100 more years if you could?
211. Do you want to live to be 100 and remember nothing, or do you want to die sooner and retain your memories?
212. If you could celebrate only one holiday every year, what would it be?
213. Would you rather spend time alone or with your family?
214. If the weather is good, would you rather do indoor or outdoor activities?
215. Would you like to attend any of these events? (Ex. Lollapalooza, Macy’s Thanksgiving Day Parade, etc.)
216. Do you remember when, where, and how long you enjoyed your best road trip?
217. What would you prefer to do in a week in New York City or Los Angeles?
218. Have you ever gone camping? What was the most enjoyable part?
Hypothetical Questions about Love
The hypothetical questions allow you to explore various aspects that you may have overlooked. You would have had these conversations before, but the hypothetical questions will allow you to make your conversation interesting and cozy. Perhaps you will learn something new about your partner.
219. What’s the difference between loving somebody and being in love with them?
220. What has your past love life been like? Do you think it was true love, puppy love, or lust?
221. Do you regret anything you did or didn’t do in your last relationship?
222. Are there multiple people for each of us out there, or do you believe in soulmates?
223. Are you a believer in fate or destiny?
224. Do you ever think of opening up our relationship? How do you feel about this?
225. In a romantic relationship, what is the one thing that you must have (trust, affection, honesty, financial stability, etc.)?
226. What language would you use to express your love?
227. If you were featured on a dating show, how would you ask questions?
228. What would you prefer to stay in, a penthouse or private beach?
229. Is it better to hold your hand for four hours continuously every single day than to never touch it again?
230. If you could choose between flowers every week and diamonds every two years, which would you choose?
231. If you had to choose, would you rather support your partner’s dream of being an influencer, or would you rather your partner be unemployed?
232. Would you rather have all our arguments live on Instagram, or use the Internet never again?
233. If you had to choose between marrying someone who never did the dishes the way you liked it or not marrying at all, which would you choose?
Hypothetical Questions for Adults
Do you want to have a more intimate conversation with your partner? Here are some sexually stimulating questions that will make you more intimate with your partner.
234. Would you prefer to sleep naked?
235. Where are the craziest places you have had sex?
236. Is there anything about sex that makes you uncomfortable? If so, then what is it?
237. Watching 50 Shades Of Grey is more entertaining or reading 50 Shades Of Grey?
238. What would you rather be called, overly emotional or cold?
239. What would you like better, the lights on or the lights off?
240. If you sneezed when you orgasmed or sneezed when you orgasmed, which would you prefer?
241. Would you rather spank someone or spank yourself?
242. If you could never wear sweatpants again, would you rather wear sequins forever?
243. Would you prefer to go back in time so you could know me better or would you prefer to spend more time with me in the future?
244. Would you rather give or receive a lap dance?
245. What would you prefer to be kissed on the lips or all over the body?
246. If you were restrained, would you rather do it or be restrained?
247. Is it better to dress up and have a sexy night on the town, or stay at home in sweats and cuddles?
248. What would be more romantic? A make-out session in an elevator or a taxicab?
249. Would you prefer to hold hands with someone or have a hand placed on your back?
250. Is there a specific Spotify playlist you prefer? Or would you rather turn up to your high school make-out mix?
251. What would you prefer, getting matching tattoos or getting a tattoo with my name in a secret spot?
252. What do you prefer, knowing my romantic fantasy or telling yours?
253. What would you prefer, being blindfolded or me wearing a blindfold?
254. Which would you prefer, a committed relationship or friendship with benefits?
255. If you had to choose, would you rather be with a stranger or with your platonic best friend?
256. If you were to have sex anywhere, would you prefer that it be “in public” or secret?
257. Would you prefer a lackluster proposal to none at all?
258. Would you rather accidentally share nudes with your parents or a stranger?
259. If you were to make out with someone at a funeral or a nightclub, what would you choose?
260. What would you prefer, walking around the house in underwear or without it?
Hypothetical Questions for Kids
When you are looking for more time to spend with your kid, these questions are perfect to let them dream, imagine, and have fun. It’s a fun way to interact with kids while enjoying the conversation.
261. Imagine that you had the option of eating either ice cream or pizza for an entire year. If so, what would it be?
262. If you could have either the ability to fly or disappear, which would you choose?
263. Do you wish to be a great dancer or singer?
264. How would you feel if you got to choose between a shark’s head and a human body?
265. Would you prefer to slide down the slide or jump on the trampoline?
266. Which would you prefer to protect, an alien or an endangered species?
267. What would be your first choice, to have three eyes or three ears?
268. If you could be either math or musical genius, which would you prefer?
269. Would you prefer to slide down the slide or jump on the trampoline?
270. Which would you prefer to read, yourself or someone else?
271. Which would you prefer to ride, a camel or a horse?
272. Is it more fun to play video games on your phone or video games on your computer?
273. Which would be more fun, putting up Christmas decorations or preparing dinner?
274. If you could see either a dinosaur or a dragon, what would you prefer to see?
275. What would you prefer, a shooting star or a rainbow?
276. Would you rather take a hot shower or a cold shower?
277. If you have the choice to transport one furious elephant anywhere in history, where would you place it?
278. If you could sleep beside either a skunk or a pig, which would you choose?
279. How would you feel if you slept in a dirty or noisy room?
280. What would you prefer to sleep in a pitch-black room or with some nightlight?
281. Which room would you prefer for sleeping in your room or your parent’s room?
282. If you were to sleep next to someone who snores or farts in their sleep, what would you prefer to be?
283. How about sleeping next to someone who rolls over a lot in their sleep or someone who talks in their sleep?
284. Where would you prefer to sleep, sofa or hard bed?
285. Which side of the bed would you prefer?
286. What would you prefer, wear socks or not?
287. What is more comfortable for you, sleeping with the lights on or off?
288. Which would you prefer to spill on your clothing, a drink, or food?
289. If you could decide between staying up late and going to bed early, what would be your preference?
290. Which would you prefer to visit, the Eiffel Tower or Buckingham Palace?
291. Which would you prefer to visit, a beach or a national park?
292. Is a museum more exciting or would you rather go to a lost city?
293. Which would you prefer to visit, an amusement park or a fish aquarium?
294. Would you rather hike or swim?
295. Would you rather visit Hawaii Volcano National Park or Glacier National Park?
296. If you had to choose between Millennium Park and Glacier National Park, which would you choose?
297. What would you do if Jurassic Park actually existed?
298. Which would be more comfortable for you, shorts or trousers?
299. If you have the choice between wearing SpongeBob pajamas or Dora the Explorer pajamas?
300. Which is worse, ugly shoes that are too big for your feet or shoes that are ugly?
Over to you…
The right type of conversation can brighten up a room whereas a partner that does not engage can make it tense. Ask these questions to make it more interesting and lively.
Additionally, it is important to know when to ask a particular question. Timing plays a huge role. Make a mental note of what you found most interesting and striking that will lead to an interesting and enjoyable conversation.
Navya is a freelance writer, avid reader, and traveler. She loves writing about personal development, spirituality, self-help, travel, and lifestyle. An ambivert and believer in miracles. She finds reading and writing very therapeutic. Her philosophy in life is to live life fearlessly and open up to the endless possibilities of life. Navya aspires to bring change by adding value, happiness, and awareness through her content on ThePleasantConversation.