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450 What If Questions to Ask – Your One-stop Guide

450 What If Questions to Ask – Your One-stop Guide

Updated on May 17, 2022 | Published on August 14, 2021
Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling), Life & Relationship Coach
450 What If Questions to Ask - Your One-stop Guide

What if questions are icebreakers and thought-provoking questions that can add humour, spice, and trigger so many emotions at once. What if questions can be asked to anyone including your kids, girlfriend, boyfriend, stranger, friends, and even to yourself. 

The questions will challenge you to go beyond the ordinary and come up with creative answers. There is no end to the list of what if questions, but here is the list of questions that will blow your mind and give you great discussion topics. 

450 What If Questions to Ask - Your One-stop Guide
450 What If Questions to Ask – Your One-stop Guide

Best What If Questions 

Adding some intriguing what if questions to your conversations will add some fun, creativity, and laughter to your daily talks. You can ask these questions to anyone and anywhere to start a friendly and fun conversation. 

1. If you were a scientist, what would you do?

2. Even if you had lots of friends, what would you do if they weren’t quality friends?

3. If you discovered that your sister or brother existed, but you didn’t know about them, how would you react? 

4. What if a fortune cookie told you something? Would you listen to it? 

5. Which scent would you miss the most if you were unable to smell again? 

6. Would you rather die or let someone else die instead? 

7.  If you were to donate to a charity, which one would you choose and why?

 8. What if you realized that you were just dreaming? Would you be glad or sad? 

9. What if you always succeeded? Would you be able to try everything that you wanted? 

10. What subject and what grade would you teach if you were a teacher? 

11.  If you could never lie, what would you do?

12. If your guys had sleepovers and pillow fights like your girls do, would you join them? 

13. Is there anything you would give up if you had to? 

14. Do you think you would run away if you committed a crime or would you surrender? 

15. Would it be better or worse if no one could make mistakes? 

16. Would you be scared if there were no rules in the world? 

17. If guys had to get their nails done at a salon, would they enjoy their time?

18. Would you like it if life was simple? 

19. What would happen if your deepest, darkest secrets were revealed? How embarrassed would you be? 

20. If you could freeze time, how could you move people out of their frozen positions? 

21. If you could read minds, what would you do? 

22. Would you use x-ray vision if you had it? 

23. What if you could ask any question to your friend and they had to tell the truth?

24. What if YOU were a poker player, would YOU utilize it to win at gambling? 

25. What if you could control people’s actions without their knowledge? Would you use such a power? 

26. What if you didn’t get sick, would you sleep all day or stay awake all night? 

27. If your body could flex like rubber, what would you do?

28. What if you were able to turn your head 360 degrees? 

29. Where would you go if you could fly? 

30. If you could alter who you were in a few seconds, would you? 

31. What if you could ask Superman a question? 

32. What if you were able to ask the Joker a question?

33. Imagine if a favourite superhero would answer a question you had? 

34. If Batman was asked, “What is your biggest fear,” what would he say?

35. If a celebrity you love started a trend, what would happen? Will you always follow that trend? 

36. If you were seen in public by a celebrity without makeup or wearing your worst clothing, how would you react? Is it more embarrassing or does it not matter to you?

37.  If you had the opportunity to ask the most famous person in history a question, what would you say?

38. If you could ask the richest person to ever live a question, what would it be?

39. What if you were allowed to ask one question to President Obama

40.  What if you had the opportunity to interview your favourite celebrity? Would you be nervous? 

41. If you were a celebrity, which one would you be?

42. How would you feel if you met someone from the past? 

43.  What if one of your friends became famous? How will you take advantage of it? 

Funny What If Questions

To add a little creativity and fun to your conversations, ask funny, what-if questions. It allows you to think outside the box and let your imagination run wild. Get ready to laugh heartily as well as discover your own unexplored thinking. 

44. What if every one of us had a talking donkey companion like in Shrek?

45. What if the ground “squeaked” beneath our feet every time we took a step?

46. If you only received money for the rest of your life in the form of gallons of Coca-Cola, how would you live?

47.  If dogs walked us, what would happen?

48.  What if you were only allowed to wear your sixth birthday outfit at your wedding?

49.  What if our house was surrounded by gardens, and sunflowers were our walls and vines were our roofs?

50.  What if we wore bathing suits as formal wear and formal wear as bathing suits?

51.  What if we could envision anything we wanted exactly as it is? Would you like blue hair? Do you want to have a giant butt?

52.  What if an animal wore false eyelashes instead of fur? 

53. What if aliens were our landlords and if we did not pay rent on time. They would abduct us to other planets where they would also have renters?

54. . What if skateboards lived and instead of pushing off against the ground, simply ran when you told it to stop?

55.  What if the stars were lights on cameras watching everything you did? And a person up in the sky watches our videos and laughs at everything we do. What would your reaction be?

56.  If humans were like horses and donkeys, we would get hoove-cures instead of pedicures, and instead of shoes, we would wear horseshoes.

57.  What if plants and trees communicated and discussed our outfits when walking through a forest and taking pictures? What if a tree posed like a girl on Instagram?

58.  What if we let songs that are stuck in our heads play loudly so everyone could hear them? Imagine, In a crowd, how insane would that sound? 

59. What if we turned to the computer instead of doing laundry, and when we changed clothing, it changed on us instantly, such as a video game?

60. What if, as the shutter clicked, we heard a woman screaming in the background. 

61.  Imagine if you could live for a thousand years, what dreams would you want

to fulfil? 

62.  If the people on the planet suddenly vanished, how would you feel? 

63. What if your fairytale comes true? 

64. If you lived in a luxury house, what is your must-have list? 

65. What if you have the opportunity to design your home without thinking of money, how would you style it? 

66. What if you have the offer to join any band for a day, which band would you choose and what instrument you would like to play.  

67. What if there was no drama? Would that be okay with you? 

68. What if you got the chance to visit one country for free, which would it be? 

69. How would you feel if you were able to work at Disneyland? 

What Would You Do If Questions

Many times you will find yourself curious about others’ reactions to certain situations. 

You can use this hypothetical question to learn about someone close and find out new things about them. Don’t forget to add a little punch of your own to these questions. 

70. What would you do if you are not able to eat anything for a week?  

71. How  would you react if you find out that someone is cheating  on you 

72. How would you feel if I did not accept your proposal?

73. How would you respond if you were confined in a box?

74. What would you do if I told you a lie about something important?

75. Imagine if we lived in helium balloon houses floating just beneath the clouds and we used other balloons attached to tracks to get around?

76. What would you do if I destroyed your official documents just because I was angry?

77. What would happen if the world ended tomorrow? 

78. Would you be able to handle a dragon stuck under your bed?

79. Would you accept my apology for never loving you?

80. What would be your reaction if a celebrity you do if a celebrity publicly gives you a shoutout on Instagram without asking?

81. What would you do if we were the only people on Earth?

82. What would you do if you have a crush on someone and you like them, too?

83. What would be your reaction if I kissed you?

84. What would you do if your favourite celebrity kissed you without your permission?

85. What would you do if you were the ugliest thing on earth?

86. What would you do if weekends weren’t part of the week?

87. What would you do if you could buy love from the market?

What If Game Questions

Games allow creativity to flow freely and increase the power of imagination, resulting in the healthy development of brain cells. 

These What-if questions are framed in a way that will encourage you to think outside the box and allow you to think creatively about your answers. 

88. What if (a famous novelist) had been a playwright?

89. What if everything we spoke was rhyming?

90.  If you could live wherever you wanted, where would you go? What city would you live in?

91. What If you discovered that snakes were living in your house, what would be your reaction? 

92. What if you had your own money tree in your yard?

93. What would it be like if you were able to write a bestselling novel? Is it going to be a romance, mystery, or factual account?

94. What if you excelled at a sport? Could you tell me which sport you would choose and why?

95. If you could do that one thing that will make you famous? What would you do?

96. If you had the choice of any job, what would you choose?

97. If you were able to come up with new food, what would it be? How would it taste?

98. If you married a famous person, what would your life be like?

99. What if you were limited to wearing only one colour all your life? What colour would you choose and why?

100. What will you do if you lose everything tomorrow? Who would you go to for comfort?

101. What if you didn’t have to work again?  What would you do?

102. If you have the power to send a message to all of humanity, what would you write?

103. What if you could rebuild your life from scratch? How would you do it differently?

104. If I showed you a movie about my life up until now, what would it be like? How would you feel about it?

105. If you were to speak to a friend as you speak to yourself, how would it be? Do you think that friend would stay your friend?

106. What if you could teach one thing to everyone, what would you teach?

107. What if you gave everything up in pursuit of your dreams?

108. If you had to choose between a wonderful romantic spouse with whom you would only be married for a short amount of time and a boring unromantic one your entire life, what would you choose? What is your choice and why?

109. What if you made the most of every minute of your life? 

110. If you had to choose between money and love, or no money what would you pick and why? 

111. If your sight or hearing were taken away, what would you do? If you had to choose, which would you pick and why?

112. What would you do differently if bank robbers broke in while you were inside, what would you do differently to save people. 

113.  If all animals were able to fly, what would it be like? 

114.  If dinosaurs still lived, what would it be like?

115. What if you asked your dog what he liked to do? 

116. What if we talked to each other like gorillas?

117. What if you had nine lives like a cat? Will you use them all that fast or will they last for a long time?

What If Questions for Kids

If you often find it difficult to spend time with your child or are unsure of how to begin the conversation. 

You can use these what-if questions to jumpstart the conversation and get it going. 

118. If you were invisible, what would you do?

119.  If you were president, what would you do?

120.  If you were given the chance to realize your dreams, what would you do?

121.  If everyone was happy what would you do differently? 

123. If you were a god what would you do differently? 

124.  If everyone vanished into thin air, how would you react?

125.  If you had the abilities of an adult, how would you live?

126.  What would you do if you were left alone for the whole week at home?

127.  If you have superpowers then how would you use them? What power would you like to have? 

128. If everyone in the world was confused and emotional except you, what would you do?

129.  If you were dismissed from school, how would you react?

130. If your class teacher catches you doing something contrary to the rules, what will you do? 

131. If one of your classmates is being jealous of you, how will you respond? 

132. What if every single thing in the world were made up of cheese? 

What If Questions for Couples

If you feel that the same old questions are boring you on these date nights, then you need to become a Love Wizard and inject some romance, love, and intrigue into your conversation. 

You can create a closer relationship with your partner by asking them interesting questions. 

133. If you have the choice of dating my best friend and or me dating your best friend, what would you choose? 

134. If someone asks you to end our relationship, knowing that I want to end it, what will you do? 

135. Would you prefer that I catch you cheating or that I find photos and videos of you doing it on your phone?

136. Would you rather befriend a strong and athletic guy, or a sweet, calm person with emaciated, skinny looks?

137. If you have to choose between two dates, one is older than you and the other younger than you, who would you choose? 

138. If you choose between a skinny partner and one who has more weight? Who would you prefer?

139. Would you prefer we love each other in private or we proclaim our love to everyone and risk the world tearing us apart?

140. If you want your parents to know about your relationship then how do you want them to find out? 

141. Which would you prefer if I found you kissing, or if you found me kissing someone else?

142. Would you prefer me to be in a video with someone else or simply photos?

143. If you were to date someone of another race, would you rather date someone like you?

144. If you could have a sexual encounter that lasted 3 minutes, or 3 hours non-stop, which one would you choose?

145. If you have the choice to dump someone or get dumped by someone. Which one would you choose?

146. Would you rather have your body photographed or have it taken of you?

147. Would you rather have an irresponsible partner who loves like no one else or a responsible one who doesn’t care about you much?

148. If you had the choice of seeing two men fighting for you or two women fighting for your men. Which one would you like to see?

149. What would you prefer, ice cubes or hot water?

150. Which would you prefer to do first? If you were playing right now, would you want to make out with someone playing this game or go on playing for hours?

151. If you outlive your partner, would you rather it be you or them?

152. Would you rather never have kids and never get married, or have kids and never get married?

153. Does it matter if your partner has lots of friends of the opposite gender or none at all?

154. What would you prefer to die with, having no regrets or many?

155. If you meet your life’s partner in high school or at 30, would you rather meet them then?

156. If your son was crying at home alone, what would you do?

157. If a child is afraid of a particular character, what should you do?

158. If you found out I didn’t have a penis/vagina, what would you do?

159. If you discovered that you are not the father/mother of your children, what would you do?

160. If you had the power to see into the future and the past, what would you do?

161. If you have to sacrifice your life for someone you love or if the person is willing to give up their life so that you can live. What will you do in that situation? 

162. If you woke up and found that your house is on fire.  What would you do?

Good What If Questions

To spend some quality time with your loved ones and to keep the conversation going, you can ask these interesting what-if questions. 

163. If given the option of receiving great wisdom or great wealth, what would you choose?

164. If you could have a second chance at birth, where would you like to be born?

165. If I gave you a second chance at life, what kind of person would you be?

166. If you were handed one million dollars, how would you spend it?

167. What if you could mould your partner however you wished? What kind of partner would you choose?

168. If you had the chance to make three wishes, what would you wish for?

169. If you had the power of God, how would you send out a message?

170. If you had to only take three things with you to a deserted island, what would they be?

171. If you and one other person were stranded on a desert island, how would you cope?

172. If you were invited to a tea party at the home of Queen Elizabeth II, what would you say?

173. What would you change if you were president of your country?

174. If you were in a car crash, what would you do first?

175. If you could choose a person to receive praise from, who would it be?

176. What would you like to hear from them? 

177. If Someone planned a surprise party for you, would you enjoy it or find it annoying? 

178.  If you had the chance to be a singer or dancer, what would you choose? 

179.  If you could choose a movie that symbolizes your life story,  which movie would it be?

180. What if we had personalized musicians who followed us wherever we went, and they played music based on the moment? 

What If Questions to Ask your Girlfriend

If you want to know your girl better, you should ask her those romantic and crazy questions that you’ve been longing to ask her for a long time. 

These questions can be asked by playing a game where you can mix your own questions with the what-if scenarios. The game will allow you to get answers to your questions while having fun and feeling close to each other. 

181. If tomorrow would be our last day together, what would you do to make it special?

182. If you received a pregnancy test right now, how would you react?

183. If you had the opportunity to star with me in a romantic movie, which one would you choose?

184. If we are in a public space surrounded by people, would you kiss me in front of everyone?

185. If I had to move halfway across the globe, would you join me?

186. What are three things you would save if your house were on fire?

187. What would you have as your only meal for the rest of your life?

188. If we were to win the lottery, how would we spend the money?

189. What if only one of [her favourite foods] remained? Would you share it with me?

190. If I had a different appearance, would you still love me?

191. If you could correct one of my faults, what would you change?

192. What if that first kiss you ever had was your only kiss for the rest of your life? 

What if Questions to Ask your Boyfriend

It does not matter if you have been dating each other for a long time or if you are just dating, these questions will help you to get closer to him and improve your relationship with a pinch of fun, love, and wildness. 

193. What’s something we haven’t done yet together with what you want us to do?

194. Would you consider long-distance if I had to move very far away for some reason? Do we remain together or do we separate?

195. If you had the opportunity to visit one place in the world for a month, which one would you choose? 

196. If you could ask me anything without being scared, what would it be?

197. If you realized that our relationship isn’t working out. Will you leave me or will you try to work it out? 

198. If we no longer had a relationship, what would you miss the most?

Best What If Questions

You can use these what-if questions to get your conversation started and enjoy discovering the possibilities of life. Let your imagination soar, don’t limit it. 

199. If the moon never formed, what would the world be like?

200.  What if humans had twice the intelligence?

201. If all cats died suddenly all at once, what would happen?

 202. What if we were closer to the edge of the Milky Way?

203. If you could be a bird and fly high in the sky for a day. Which bird would you pick?

204. If you could be a plant for a day, which one would you be?

205. If it were possible for you to be a superhero, which one would you be?

206. If you could live the life of another man or woman for a day, who would you choose?

207. If you could swap personalities with one person for a day, who would it be?  

208. If you have the chance to impact the world in any way, what would you do?

209. If you could decide how and when you wanted to die, what would you choose?

210. If you were given the choice of living on another planet, which would you choose?

211. If someone gave you a million dollars for changing your identity, would you? 

212. What would you design on Hallmark cards if you were to do so? Is there anything you want to say inside the greeting?

213.  Would you enjoy being a pilot if you became one? 

Crazy What If Questions

Sometimes people take life too seriously and miss out on the fun. Every person has a crazy side that people do not know about. 

With these questions, you’ll discover your wild side and come in touch with your inner crazy man. 

214. What if you could only be with one person forever?

215.  What If You Could Preserve One Memory of Us? Which would you choose?

216. If you were able to eat only one food for the rest of your life, what would it be and why?

217. What if we didn’t have gravity? 

218. What if we grew vines and flowers right out of our heads instead of hair? And the facial hair matched the body’s hair.

219.  What if your life were live-streamed 24/7 on the TV? Would people watch it? 

220. If a clown were to walk then how would he do? 

221. What if we lived among dragons? Wouldn’t it be amazing if coworkers and boyfriends/girlfriends were dragons as well?

222. If you can only work with your index fingers, how would you do it?

223.  If you could only eat with your toes only, what would be your reaction?

224.  If zombies existed, what would happen? 

225. Wouldn’t it be cool if you could get a Disney character’s view on being in a film? 

226. How would you feel if you were hypnotized? Would you choose one question or word to trigger hypnosis? 

227. What if tattoos were dry erase boards, and you could wipe them off whenever you didn’t want to have them, and then rub them in the opposite direction to reapply them?

228. What if there were mermaids in lakes and crazy creatures and they protected us when we went swimming from big and angry sea creatures that wanted to eat us? 

229.  What if you had the option to choose between having a butler or a personal chef for a week? 

230. If your parents left you something in their Will, what would it be? 

231. What if you told me everything you thought? 

232. What if children ruled the world? 

Deep What If Questions

Your mind may often wander to thoughts of life, death, success, and other elements of life. Having someone to discuss these topics with will allow you to gain a new perspective and find answers to some of your deep questions. 

By asking deep what if questions you will be able to start and sustain the conversation. 

233.  If there is no reason for living, what would you do?

234. If you don’t achieve your dreams, what would you do?

235. What if a fortune-teller told you your missions in life? Would you ever believe it?

236.  If this was your first life, who would you be next time?

237.  If you have to live the same day every day. What would that day entail? 

238. What if you won’t succeed every time, will you die of hopelessness?

239.  If you were given another chance on your deathbed, would you take it? 

240.  If you died today, what would most likely be remembered about you? 

241. What if you suddenly gained a new strength? Which strength would that be?

242.  If life were meaningless and there was no purpose in life, what then? 

243. If you were able to contact your past self, how would they tell you about their future lives?

244. What if there was an apocalypse, would you live? 

What If Questions about Life

Do you tend to reflect more on your future or on the mistakes you have made in the past? To engage in a deep conversation about life and its complexity, here are some interesting what-if questions. 

 245. What if you have to choose between living in the countryside or the city? 

246. What if you have to choose between being an officer and a firefighter?

247. What if your past could be rewritten, would you do it?

248. What if your current career didn’t suit you, would you change it or stay put?

249. If your future self interviewed you in 10 years, what would she say you have accomplished? 

250. What if you could predict the future for other people without knowing the outcome? Would you go ahead and tell them what happens? 

251. If you had to choose between cremation and burial after you died?

252. If you were to teach one valuable lesson to your children, what would it be? 253. What if you ran out of money and needed help from your family until you could support yourself again?

254. If you lived in a tiny house, would it save you most of your money?

255.  If you had the power to choose your children’s gender, would you do so? 

256. If your children could choose which characteristics they would have, what would they be like? 

257. If your children were left with one question to ask every person they met, what would it be? 

258. What would you do if you lost your job?

259. If you got a promotion at work, how would you feel? Can you ask for a raise if you don’t get one? 

260. If you won one million dollars, what would you do? Would you spend it in a clever way?

261. If you owned a business, how would you manage it? What kind of business would that be? 

262. What if success and happiness were to be weighed against each other? Which path would you choose if you had the choice? 

263. If you had the choice to choose any job, would you choose an interesting job with little pay or a boring one with great pay?

264. If your child looked just like you, would you be happy?

265. Imagine if you could predict the future? 

266. If you were able to ask your future self one question, what would it be? 

Great What If Questions

Your thoughts are the food for your mind. The most effective way to spur your creative juices and discover new things is to have great conversations. These conversations will help you think differently and expand your horizons. Here are a few great what-if questions to stimulate your creativity. 

267.  If you could climb trees and swing like a monkey, what would you do? 

268. If animals ruled the world, what would it be like? Which animal do you think would be at the top?

269. What if all animals spoke English? 

270. If you played an antagonist in a movie, what character would you be? 

271. What would you be if you were the leading character in a movie?

272. If you were to write a book, what would it be about? 

273.  What if the entire solar system was habitable?

 274.  If cars could fly, what would they look like? 

 275.  If you were interviewing for a job, would you appear calm and confident or nervous?

276.  If you saw the wrong question being asked by a colleague, would you speak up? 

277. What colour would you be if you were a colour, and why?

278. If you had to be a fruit for one day, which would you be? An apple or a banana? Why?

What if Questions to Ask Friends

With your friends, you can talk about anything you like, no matter how glib or complex. Here are some interesting what-if questions that will make you laugh, think, or even get excited about the outcome. 

279. If police tried to arrest you for no reason, how would you respond?

280.  What would be the reaction if you woke and realized you could not move your body?

281. What if your friend steals things from you?

282. What would you do if you suddenly received a $1 million gift?

283. If a stranger kicks you in the balls and runs away, how would you react?

284. If the government lets people commit crimes and they’re not punished, what will you do?

285. If you won the lottery, what would you do?

286. If someone found out your biggest secret, what would you do?

287.  If the electricity in the world stopped, what would you do?

288.  If you could have everything your heart desires for free but had to live without the internet?

289.  If you become a celebrity, what would you do?

290. What would you do differently if you only had five years to live?

291. If you weren’t afraid of anything in the world. What would you prefer to do and why?

292. If money didn’t matter. What would you do?

293. What if the Law of Attraction actually exists?

294. If the South won the Civil War, what would happen?

295. What would you do if all the seas dried up?

296. What if computers took control of the world?

297. What if you cannot buy happiness with money? Is it possible to be happy without money?

298. What if no one hears anything?

299. What will you do to ban plastic in the world? 

300. If you woke up tomorrow and suddenly couldn’t speak your native language – only a foreign language?

301. If you were mentioned in a story, would you like it? What kind of character would you be in your story?

302. What if happiness cannot exist without sadness?

303. If a cure could be found for a particular disease? If you could cure one disease, which would it be?

Cute What If Questions

Even a small gesture may have a lasting impact. In a relationship, it’s really important to keep that spark alive. Whether you are just starting a relationship or have been together for some time. This shows your partner that you care for them and are interested in finding out more about them. 

304. What if I keep your hand on your waist for the whole day?

305. Which would you prefer, watching sunsets or movies? 

306. If you have to choose between kissing on the cheeks or the forehead. Which one will you choose? 

307. If you have to choose between a kiss on the cheek and a peck on the lips. Which one would you prefer?

308. If you had to choose between cuddling under the stars and a blanket, which would you choose? 

309. What would you prefer to see me in a bathing suit or underclothes?

310. If you have to choose between wearing my t-shirt or one of my body-con cami tops?

311.What if we got stuck in the jungle for the whole night? 

312. What would you prefer, going to the photo booth or taking silly selfies?

313. What would you choose to prepare breakfast daily or have candlelight dinner together?

314. What if you have to choose between taking a shower with me or kissing me all the time?

315. If you had to choose, would you kiss on the first date or wait for a few dates?

316. What if we went on a night out with your friends and I proposed to you? What would your reaction be?  

317. If you had to choose between travelling the world or having a family, what would you do? 

318. What if you could explore outer space and the depths of the ocean? Which one would you prefer?

319. Which would you choose between a pedicure with me or a massage? 

320. If you could choose, would you prefer to receive a gift that was bought instead of made by yourself? 

321. If you could be a butterfly, what would you do? 

322. What if you had the opportunity to go on a fairy tale in real life? 

323. What if I made your hair every day caught for you? 

324. What if I hugged you every hour of the day and night for the rest of my life? 

325. If we wore the same colour dress for the rest of our lives, would we be bored? 

What If Dirty Questions 

Are you curious about your partner’s fantasies and secrets? These questions will help you uncover deeper aspects of your partner’s personality and build an intimate relationship with them. 

326. If I told you my dream romantic fantasy, what would you prefer to hear?

327. Would you rather be blindfolded or have me wear the blindfold?

328. If you could have sex at any location in the world which one would you choose?

329. If you could make me do anything you wanted. What would you prefer? 

330. If I kissed your entire body for a long time, what would happen?

331. What would you do if I caught you masturbating? Are you going to stop or will you finish? 

332. If I was out for dinner and asked you if I wanted sex right now, what would you do?

What If Sex Questions 

If your relationship lacks the spark and intimacy and your daily conversations are boring and lifeless. Try asking your partner some intimate questions if you want to create an intimate environment and bring you closer together.  

333. What if you have to choose between kissing on lips or your nipples? What will you want me to do? 

334. What if I screamed the name of my ex while having sex with you? How would you react? 

335. If you have to have to choose a sex position for the rest of your life which one would you choose and why? 

336. If you could have sex with one famous person, living or dead, who would it be?

337. What would you choose giving blowjobs or receiving? 

338. Would you consider pegging at some point?

339. If I’m with you, what part of my body do you want to lick first?

340. What would be your reaction if I told you that I can make your sexual fantasies come true? 

341. What would you do if allowed to experience sensory deprivation using both a blindfold and earplugs? 

342. What if we had sex while watching a pornographic show and it wasn’t planned? 

343. What would choose rough sex or gentle? 

344. If you could not use one sex position for the rest of your life, which one would you choose? 

345. If we had to integrate a food item into our sex, which one would we choose? 

346. If everything was up for grabs, what would you want me to do to you?

347. Would you choose to have the stimulation of only three erogenous zones in your body?

348. If there was only one sex toy you could use forever, which would it be?

349. Who would you invite to be our third guest if you could invite any celebrity? What do you think will happen?

350. What would you do if you could only use your hands on me?

351. If I could only taste you with my mouth, where would you like me to taste you?

352. Which outfit would you choose to dress me in if you could? You can do anything you want!

353. What does it feel like for you to orgasm?

354. What would you do if I were with you right now

355. What type of woman would you prefer, a dominatrix or a submissive?

356. If you were given the option to have sex with your ex, would you take it? 

357. If you had to pick one of mine to have sex with, which one would you choose? 

358. What would you choose right now if you had to choose what I had to do right now? 

Romantic What If Questions 

How about making your date night even more memorable? By asking romantic what-if questions, you can get to know your partner better and enhance the feeling of love and closeness. Get closer to each other by having some deep and romantic conversations. 

359. If you had to choose between cuddling and showering together, which would you choose? 

360. If you were alone with your partner, would you prefer them to dress sexily or formally?

361. If you had to choose between being romantic and kinky, which would you rather be?

362.  If you have to choose between posting a dirty tape of us online or have our friends anonymously watch it? Which one would you prefer? 

363. If you choose between having a hot partner who doesn’t really love you or one who loves and supports you unconditionally, which would you prefer?

364. If you had to choose between staying at home and walking with me, which would you choose and why? 

365. What if we were locked in the same room for two days. Then what will you do? 

366. What would you do if I had booked a one-month vacation without telling you? What would your reaction be? 

367. What if I lost my ability to move because of an accident? Would you love me if I lost that? 

368. What would you do if a girl tried to seduce you? Are you tempted to fall in love with her? 

369. What would you say if you had only three words to express yourself. How would you go about it? 

370. What if my boss asks me to have sex. How will you feel about it?

371. If you see me talking with another girl/boy will you get jealous? What will you do? 

372. If you could change one thing about our relationship, what would you do? 

373. What if I didn’t talk to you for a week? How will you reach out to me? 

374. If you had to choose between day and night for intimacy, which would you prefer? 

375. What if I told you that I have designed a dress for you? What would your reaction be? 

376. If you were asked to read me a romantic novel, which one would you pick? 

377. If you are forced to pick between cuddling and making out. What would you choose? 

378. If you were to give me a rose or handwritten note, which would you prefer? 

379. If you were able to choose the activities that would make a perfect day, which would you choose?

380.  If you have to tell me what quality of me that you like the most? 

381.  What was the first thing that caught your eye when you first saw me? 

382. If we had kids in the future what would you name them? 

383.  What makes you feel loved the most? 

384. What if we have the opportunity to get married again? How would you like it to be? 

385.  What would you choose to eat at a restaurant or the food made by me? 

386.  If you could go back in time, what age would you be again?

387. If you could see into the future, what would you want to know?

388.  If money didn’t matter, what would you want to do for a living?

389. Which is your favourite activity for a date night?

390.  Is there any food you remember me by? 

391. What is one of your romantic fantasies?

392. What if I suddenly asked you to move in with me? What would your reaction be?  

393. What are your goals for the relationship?

394. If we can make each other better. How will you do that on your part? 

395. If you have the option to live anywhere in the world with me, where would you live? 

Scary What If Questions 

If you want to have some fun, ask your friends, partners, or colleagues scary what-if questions. The experience will allow you to let your guard down and take a break from everyday life for a while. 

396. What if the scary dream you had last night came true? 

397. If you could change the colour of your eyes. Which colour would you pick?  

398. What if you knew you were going to die in a few minutes? 

399. What if you see a ghost and suddenly you can’t speak? How would you react?  

400. What if you spotted an alien and talked to him? 

401. What if you are looking in a dark room with a horror movie playing on Tv. What will you do?  

402. If you were to die today, what regrets would you have about the life you lived?

403. If you were able to take one thing with you after death, what would it be? Why?

404.  If you could spend a day with a famous person, alive or dead, who would it be?

405. If you died today, how would people remember you?

406.  What if you have to spend a night in the forest alone?

407. If you knew that you’d die suddenly, would you change anything about the way you are? If so, what?

408. If you were given an envelope with the time and date of your death inside, would you open it?

409. What if you have the chance to achieve things before you die, would you like to do it? 

410. What if a guy about to die in the electric chair suffered a heart attack?

411. If ghosts are able to go through walls, why don’t they fall through floors?

412. If you were to commit a murder, how would you go about it?

413. If you have to spend a night at a haunted place in exchange for money. Will I do it? 

414. If you have to choose one scary character from any horror movie. Which one it would be. 

415. What if you have to sleep in a coffin for a night. 

 416. If you had to chop off a piece of your body, which would you choose?

417. What if you bought a doll that you later came to know is possessed? 

418. If you have to watch a horror movie all alone. Will you watch it?

419. If you had to choose between being bitten by zombies or vampires, which one would you choose? 

420. If you have to walk through a graveyard at night, do you have the guts to do it? 

421. If you encountered Bloody Mary in your bedroom at midnight, what would you do? 

423. If you witnessed a murder, would you go to the cops or keep your mouth shut?

424. If you came back as a ghost, whose life would you make a living hell? 

425. If you could ask the devil a question, what would it be?

426. If there’s hell, do you think you’re going there?

427. If you were trapped on an island, would you rather resort to cannibalism or die of starvation?

428. What if someone whispered in your ear something at midnight? 

429. What if you knew you were about to die. If you had one last meal, what would it be?

430. What if you spotted a person staring at you from your room window and trying to enter your room? 

431. If a dolphin turns into a shark while you’re playing with them, what would happen? 

432. What if you woke up one morning with four broken teeth? 

433. If you are afraid of heights and one day find yourself on the edge of 150 floors, what would you do? 

434. What would you do if the plane crashed while you were returning home? 

435. What if the plane you were taking was hijacked? 

436. What if spiders crawl all over you? 

437. What if you received the money in exchange for having snakes all over you? 

438. Wouldn’t it be scary if you were walking with your friends on a nearby hill and it started raining and thundering and one of your friends got burned by lightning? 

439. What if someone pranked you by lashing out their dogs behind you, and the dogs bit you?

440. Imagine you passed away in your dream? 

441. What if you found out that one of your friends is a ghost? 

442. What’s the scariest event you’ve ever experienced? 

443. If you have a near-death experience, what should you do? 

444. What if you had to taste blood? 

445. If you needed to consume human flesh to save your life, would you do it? 

446. What is the deadliest monster you are scared of? 

447. What would you do if you discovered that the house you lived in was haunted? 

448. If you could eat a chunk of a human heart, which would you choose?

449. What if you come back to life as a ghost? How would you wreak havoc on someone’s life?

450. If you had to choose, would you rather lose an arm or a leg?

Over to you…

Your conversation will start and progress much more quickly when you use the list. Sometimes it’s hard to come up with questions or topics that will pique people’s interest, and even more difficult to get them going. These questions will be your saving grace in many ways. 

Also, be careful not to hurt someone’s feelings or harshly oppose their opinion. Using these questions, you get to know people better and expand your thinking by spending more time with them. 

Fun and meaningful connections await you!