Would you rather talk about the weather or ask questions that get someone in instantly? Nothing wrong if you choose the former.
But if you’re in the latter, and most likely you are, then this list of ‘hard would you rather questions’ would surely help you.
As you might have already guessed, these questions are hard. So it would always be a call to make a tough choice. This makes it more exciting, engaging, and the perfect prompt to connect to someone effortlessly.
Sounds good? Here we go!
Hard Would You Rather Questions
“Life is a matter of choices, and every choice you make makes you.”– John C. Maxwell
Choices coming with these questions might not make your life but surely make a good conversation. It’s so versatile that you can use these easily in apparently any situation.
Be it breaking the ice, making someone laugh, teasing that person, or just bonding over a few questions, you can always steer the conversation accordingly.
Besides, asking ‘would you rather questions‘ is a classic timepass. So you can totally try this game next time when everyone is waiting for something fun. Here’s a quick guide to the game, in case you need it –
Would You Rather Questions Game
Games are fun. Especially on long drives, a get-together, a date, or any random situation where there are more than two ears and one mouth.
Bonus is – since one has to choose between two options only, it doesn’t take half of your life waiting for the response.
How to Play?
It’s pretty easy with almost no rules. Just ask questions one by one. Everyone needs to answer it in their turn. Or, you can choose to choose a questionnaire while others answer and vice versa. Importantly, the questions need to create a dilemma between two choices.
Pretty easy, right?
So, let’s jump to it without wasting another moment!
Really Hard Would You Rather Questions
These are the types that can keep all of you up in a boring afternoon, turning it into a heated debate.
Don’t worry the debate would be only about convincing you why your choice is the right one. Craving something interestingly hard? Here we go.
1. Would you rather look dumb and be smart or look smart but be dumb?
2. Be a part of utopian fiction or dystopian reality – what would you choose?
3. Would you rather lose the ability to express yourself or lose the ability to understand others?
4. If you had to abandon one for life, would you choose to leave using any kind of cell phone or using any kind of automobile?
5. Would you live in a world where no one has the ability to love or in a world where no one is allowed to love?
6. 20 minutes of extreme pain but then no pain for life or minute pain all your life – what would you choose?
7. Would you rather live for 100 years but in poverty or live for ten years as a rich person?
8. Stay all your life locked in a room with all comforts and luxuries or never get a good home but have freedom?
9. Would you rather stay friends with your crush for a year or lose them entirely after dating for a week?
10. If from now onwards, you’re either only able to watch a movie, that too without subtitles, or listen to it without visuals, what would you choose?
11. Would you rather sleep half a day for the rest of your life or never be able to sleep in life again?
12. If you had to choose one, would you rather spend a day in an unknown place with your ex or completely alone among strangers?
13. Would you rather date your long-term friend or be friends with your long-term romantic partner?
14. Give up your real social life for a month or give up social media for a year?
15. Would you rather have free wifi for life or free books for life?
16. Meet your favorite person at the wrong place or the person you hate most at the place you are looking for any known person?
17. Would you rather become the president of the United States or king of an unknown country?
18. Read people’s minds or listen to their true feelings about you when you meet them for the first time?
19. Would you rather be the worst player in the best team or vice versa?
20. If you had to choose one – would you rather be a talentless popular person or a talented person no one knows about?
Hard Would You Rather Questions for Adults
All of you are here, waiting for prompts to ignite a discussion. So, all you need is a list of questions that make everyone give a thought about their choices.
Plus, these questions are specially curated for grown-ups to make it super fun and hard.
21. Would you rather give up good sex or good food?
22. Share your browsing history to your company mail or visit your office in pajamas?
23. Only get to have a nightstand once a year with your partner or have a threesome with a stranger whenever you want?
24. Would you have your parents walk in on you when you’re doing it? Or, would you rather walk in on your parents?
25. Be a prisoner for life or a homeless person for life?
26. Would you rather witness a murder or find a dead body under your bed?
27. Kill someone innocent who is going to die anyway or kill 2 violent criminals who might commit a murder?
28. Would you rather never ask your crush for a date or ask them out but get rejected?
29. Have a stable life with no change at all or an unpredictable dynamic life?
30. Would you rather have your loved ones disappointed in you or be disappointed by yourself?
31. Marry someone you find attractive while they don’t find you the same or marry someone unattractive while they find you attractive?
32. Would you rather have your every dream come true, including the bad ones, or get you every thought ever read by a stranger?
33. Get visibly nervous every time someone greets you or make everyone nervous every time you greet someone?
34. Would you rather always have dripping sweaty underarms or uncontrollable laughing every time you are with your crush?
35. Be in your 20s all your life while your spouse is growing or let your spouse be in their 20s while you are growing?
36. Would you rather get a promotion now knowing you don’t deserve it or take a promotion after 5 years when you deserve it?
37. Have the ability to pause anything in life or the ability to go back in the past?
38. Would you rather always look too dressed for the occasion or always underdressed for any great day?
39. Never have enough battery in your phone or never have enough fuel in your car?
40. Would you rather be obsessed over something or have someone obsessed over you?
Hard Would You Rather Questions for Couples
Spending some quality time together is the best thing you can do for your relationship.
These questions are designed for you to have such a fun yet meaningful conversation with your partner. Bonus, you can take it as a good couple’s communication exercise.
41. Would you rather watch a romantic movie with me or a horror movie with me?
42. Look at your partner’s search history or know about all their past relationships?
43. Would you rather cheat on your partner or get cheated by them?
44. Have a healthy relationship but long distance or a stressful relationship but living together?
45. Would you rather share each and every detail of your daily life with your partner or never share anything with them?
46. Have the smartest kid in the world or have the happiest kid in the world?
47. Would you rather have great emotional compatibility or a great sexual life with your partner?
48. Meet your partner’s ex or make your partner meet your ex?
49. Would you have your partner always nag or never share anything with you?
50. Forget every good thing your spouse did for you or always remember in detail when your spouse disappointed you?
51. Would you rather disappoint your spouse or be hated by your spouse’s family and friends?
52. Rather be held high by your spouse or find your spouse the best person in the world?
53. Would you rather always cry only in front of your spouse or always laugh only in front of them?
54. Be better than your spouse in everything or have your spouse better in everything than you?
55. If given a chance, would you rather date someone else or date your partner again this time?
56. Would you rather have a date night every week or a quality conversation with your partner every day?
57. If you had to choose one, would you rather kiss every day or cuddle every day?
58. Would you rather have a hot quarrel with each other or don’t talk to each other?
59. Have your partner tell you a painful truth or tell you a lie to not hurt you?
60. Would you rather like your partner to be too clingy or too indifferent?
Fun is for all. So if your kids are getting ‘bored’ or you have to keep a herd of them busy, these questions are the ultimate rescue.
This lets them think hard, giggle, get excited, or even confused. All in all, the game keeps them happily busy while you can bond with them. Happy play!
61. Be the president for a week or have breakfast with your favorite celebrity for a year?
62. Would you rather choose to be able to talk to animals or understand any language in the world?
63. If you could get anyone power – would you choose to read minds or to see the future?
64. Would you rather play video games or listen to stories all night?
65. Travel the whole world by boat or by hot air balloon – what sounds more fun?
66. Would you rather visit all the amusement parks in the world or taste all the ice cream flavors in the world?
67. Get to rewatch your favorite movies like the first time or reread your favorite stories like the first time?
68. Would you rather have the ability to fly like a bird or the ability to run like a cheetah?
69. Eat a raw onion with your every meal or give up chocolates for a month?
70. Would you rather have a new puppy pet or a new bike?
71. Never have to clean your room or never have to do your homework?
72. Would you rather have your favorite superhero as your friend or have your favorite superpower in you?
73. Eat a whole stick of butter or a whole spoon of salt?
74. Would you rather be incredibly smart or incredibly strong?
75. Have a bug as your pet or share your room with a dragon?
76. Would you rather have broccoli in every meal or always receive a lawnmower as a birthday gift?
77. No homework for a year or no playtime for a year?
78. Would you rather learn to play a musical instrument or to speak a new language?
79. Share your room with a monkey or your dinner with a spider?
80. Would you rather be the richest person or the happiest person in the world?
Crazy Hard Would You Rather Questions
How about some ‘would you rather questions that sound simple but drive you crazy while making a choice? Yes, please! These questions are insanely quirky so you might need to repeat them twice before the person answers them.
Good for a giggle and some intense thoughts, these questions pretty much make a great conversation.
81. Live an average life that is stable or an adventurous life which is unpredictable?
82. Would you rather date the funniest person in the room or be the funniest person in the room?
83. If you had a choice between sharing your browsing history with everyone you know or going topless for an hour in a place where no one knows you, what would you choose?
84. Would you rather live in an era 200 years ago or in a time after 200 years?
85. Never brush your teeth or give up bathing entirely – what would you go for?
86. Would you rather have spicy food or bland food for all your meals?
87. Play the character you dislike most in your favorite tv show or the best character in your most hated tv show?
88. Would you rather have cat food or dog food once every day?
89. Know the exact time of your death or the exact way of how you would die?
90. Would you rather lose all your precious materials or all your precious memories?
91. Skip red lights or skip annoying calls from random companies for the rest of your life?
92. If you knew there was an invisible person in the room at a sleepover but no one would believe you, would you rather stay silent or would you tell everyone?
93. Would you rather date your best friend or date a stranger?
94. Overwork yourself and get paid double of what you worked for it or underwork and get paid half of what you deserve?
95. Would you rather clean your house twice or do the dishes 5 times every day?
96. Be trapped in your favorite story with your enemies in it or be a part of a horror story with your friends in it?
97. Would you rather have diarrhea or constipation for a month?
98. Have delicious but unhealthy food or healthy food that tastes awful in all your meals?
99. Would you rather die of eating poisonous food or of starvation?
100. Have a sense of humor better than your partner or date someone who has a better sense of humor than you?
Extremely Hard Would You Rather Questions
Impossible questions that make you scratch your head or think too hard. Yes, these are the ones you won’t want to come across in real life ever.
Plus, these are not offensive yet difficult to answer. So, you can throw the random ones freely when you want to see the intense expressions on everyone’s faces.
101. Would you rather witness an unsettling truth that no one is going to believe in or believe in a lie like everyone else?
102. If you had to choose one between the ability to speak or the ability to see, what would you choose?
103. Would you always have terribly slow internet or very fast internet just for 15 minutes a day?
104. Ten years living without any kind of technology or ten days living without any food?
105. If you had to abandon anyone for life, what would you leave – ice cream or coffee?
106. Would you rather always seem arrogant to others or always seem too easy?
107. Live in a world with absolute freedom or a world with absolute order? Remember, the former brings crimes, later brings exploitation.
108. Would you rather give up chocolates or give up cheese entirely?
109. Be infamous in history after your death or be unknown – what would you choose?
110. Win useless stuff in a lottery or let your neighbor win something amazing?
111. Have a full-body tattoo or no tattoo at all?
112. Would you rather be taken to a dentist or a doctor while you were pretending to be sick?
113. Forget all the adjectives or all the adverbs?
114. Would you rather always sound uninterested or always sound clingy?
115. Live alone on an island with all the luxury or live with your friends in a horrible city?
116. Would you rather have the story of your life written by a horror story writer or by a melodrama filmmaker?
117. Express your anger only through songs or your happiness through cursing?
118. Be a comedian who can’t make people laugh or a chef who makes horrible food?
119. Would you like to be world-famous for all the wrong reasons or stay unknown to the world?
120. Rather live a rural life without the luxury of nature or an urban life without technology?
Hard Would You Rather Questions Relationships
Relationships are part and parcel of our lives. Why skip it in our conversations? These questions open new perspectives about relationships, letting you make some tough choices.
Good thing is, these would let you understand what matters in a relationship for you. Thus, new perspectives, insights, and realizations await you in this conversation.
121. Be together and always fight or stay away but all in love?
122. Would you rather have one true love but lose it or have a relationship without love for life?
123. Be with someone who is just like you or someone who compliments you?
124. Would you rather date someone who is hot or one who is smart?
125. Propose your friend with a risk of losing the friendship too or never confess and stay friends?
126. Would you rather make new friends everywhere you go or be with your old ones?
127. Outlive your partner or have your partner outlive you?
128. Would you rather spend more time with your family or with your friends?
129. Have kids though you can’t afford a good life for them or be financially sound but without kids?
130. Would you be rather married without kids or have kids without marriage?
131. Have a great relationship with your parents or with your friends?
132. Would you still be there with your friends if your parents don’t like them or would you rather choose your friends?
133. Have a large warm family with everyone living together or a small family with cold privacy?
134. Would you date someone you trust but don’t like or someone you like but don’t trust?
135. Do you want to date someone who is exactly like you or someone who is completely opposite to you?
136. Would you rather be in a bad relationship or don’t have a relationship at all?
137. Sacrifice your morals for your loved ones or stick to it even if it might harm your dear ones?
138. Would you like someone just because they are related to you or would you choose to be with only those whom you like?
139. A relationship in which there is love but no respect or there is respect but not love?
140. Would you rather have a relationship without any conflict o
Super Hard Would You Rather Questions that Seem Easy
Questions that seem easy in the first gaze but quite hard when you actually think. Yes, these easy seeming super hard questions won’t intimidate someone instantly but won’t be a piece of cake either.
Perfect for a fun and thrilling talk, right? So, let’s dive deeper –
141. Would you rather have a paper cut or a needle prick?
142. Time travel to revisit your past or to explore your future?
143. Would you choose to live like 20 years old when you are 40 or 40 years old when you are 20?
144. Eat only your favorite food every day, for every meal for the rest of your life, or would you never eat it again in life?
145. Would you rather only be able to eat hot dogs for a month or give it up for a year?
146. Talking funny, would you rather eat pizza-flavored ice cream or ice cream-flavored pizza – what would you choose?
147. Would you rather wear pajamas all your life or never wear them again?
148. If you get a chance, would you leave earth for a healthier planet or live here with all the pollution and climate change?
149. Would you be a smart jerk or a sweet dumb?
150. Be any of Marvel’s villains or get trapped in the Matrix?
151. Would you date a boring famous person or an interesting ordinary one?
152. Lose the ability to pretend to be happy or never be able to show it when you are sad?
153. Would you rather buy something cheap that no one could ever use or buy something costly that your neighbor can use well?
154. If you had to confess your love, would you rather do it publicly or in private?
155. Would you rather bite your lips or get your hair pulled?
156. Go everywhere for a month with a haircut done by a horrible stylist or eat meals made by a horrible cook for a month?
157. Would you rather meet your favorite celebrity for once or be neighbors with your crush?
158. Date someone who is too punctual or someone who is never on time?
159. Would you rather binge-watch Netflix all day or read your favorite books all night?
160. Spend your next 10 years single or next 1 year dating your ex?
Hard Would You Rather Questions Clean
No need to worry about too outlandish questions when you clearly don’t want to. These ‘clean hard would you rather questions are difficult yet not offensive, dirty, weird, or disturbing.
Plain and super engaging when you want to play safe but not boring. Here we go.
161. Would you be always alone or never be alone?
162. Be a horse with a horn or a rhinoceros without a horn?
163. Would you rather have nails on your head instead of hair or hair on your fingers instead of nails?
164. Always go without a shower but smelling good or with a shower but smelling bad?
165. Would you rather be an ugly chair none was to sit on or a cool one so that everyone wants you to try?
166. Either give up candies altogether or give up cold drinks completely?
167. Would you rather have the ability to be confident in yourself in every situation or be able to trust others when you want to?
168. Get awkward in every conversation or make others feel awkward every time they talk to you?
169. Would you rather be every child’s favorite or every oldsters’ favorite?
170. Date a psychopath who is genuinely good to you or someone who is normal but treats you badly?
171. Would you rather exchange your life with a pet dog or a pet cat?
172. Never use social media again or never read a book?
173. Would you rather look good in every picture or take amazing photos?
174. As a stand-up comedian, would you rather crack jokes on yourself or on others?
175. Would you rather relive your childhood or skip your old age?
176. Be friends with your parents or have your friends as your relatives?
177. Would you eat pizza without cheese or brownie without chocolate?
178. Always look too perfect or a bit messy?
179. Would you rather sound arrogant or dumb?
180. Act weird in front of your crush or act dumb in front of your teacher?
Insanely Hard Would You Rather Questions for Girls
Want to make her laugh or let her think insanely about this and that? These questions to ask a girl got your back. Not too cheesy, uncomfortable, or nosy yet hard enough to engage her instantly, what else do you need?
Be it a fab female friend, your crush, girlfriend, or just someone you want to know – these are the get-to-go prompts to make things fun.
181. Would you rather always have to explain your point twice or listen to others’ points twice to get it?
182. Marry your loved one now because they want to or wait till you are well-off financially?
183. Would you rather date someone good at expressing themselves but bad at understanding you or the one good at understanding you but bad at expressing?
184. Have a non-stop period for one month straight in a year with the rest eleven months free or bleed for one week every month?
185. Would you rather always intimidate everyone with your presence or never get noticed specifically?
186. Never have period cramps again or never get stains on your clothes?
187. Would you rather always feel a slight itch or never smell at all?
188. Have an adventurous day or a relaxed one?
189. Would you rather be great at money matters or amazing at creative things?
190. Always look like a fashion diva or never feel underconfident?
191. Would you rather get a Nobel prize for inventing something or for doing something artistic?
192. Look weak but be strong or be strong and seem weak – what is your choice?
193. Would you rather never feel tired or never get frustrated?
194. Rather be known as a compassionate person or as a very strong person?
195. Would you rather win a wrestling match or binge-eating marathon?
196. Be wise and loved or be famous and wealthy?
197. Would you rather eat delicious junk food or boring healthy food?
198. Get amazing skin or have great hair?
199. Would you rather always be loud or never get heard?
200. Go on your dream holiday or land your favorite job?
Hard Would You Rather Questions for Guys
Guys got to have fun. And these awesome questions hit home exactly that way. These are so versatile that on one hand might show his brainy side and on the other his crazy one.
So, if you want to have some fun time with him, these questions are great to get to go. Here we go.
201. Would you rather cry in front of your girlfriend or in front of your friends?
202. Have a perfect body or a perfect face?
203. Would you rather spend your weekend chilling with your friends or dating your girlfriend?
204. Give up your dream job or your soul mate?
205. Would you rather have a tough interesting job or an easy boring job?
206. Be the first person to land a new planet or the last person to leave the earth?
207. Would you rather play a terribly great villain or a not so likable hero in a movie if given a chance?
208. Rather seem strong but be clever or look clever but be strong?
209. Would you rather own a luxury car of your choice or unlimited books of your choice?
210. Either give up playing video games or give up watching movies – what would you do?
211. Would you rather get trapped in a rom-com or in a thriller?
212. Have a superpower of your choice or be the center of attention wherever you go?
213. Would you like to try knowing you won’t succeed or accept defeat without even trying?
214. Have perfect abs or hidden talent?
215. Would you rather try skydiving or bungee jumping?
216. Be the main lead of a flop movie or a side lead of a hit movie?
217. Would you rather know too much to be happy or too little to be sad?
218. Never know how it feels like loving someone or never know how it feels when you love someone?
219. Would you rather have a great marriage with someone ordinary or a great affair with someone too attractive?
220. Be invincible in anything physical or anything mental?
Most Hard Would You Rather Questions
Are you looking for questions that sound almost impossible? Like, seriously.
These hardest would you rather questions aren’t something too unconventional or deep but just at the sweet spot that makes it super interesting. Sounds good? Give it a try here.
221. Be an ordinary person in a utopian world or the ultimate powerful person in a dystopian world?
222. Would you rather always do dishes or never eat on dishes?
223. Witness the death of someone you know or get to know after they died?
224. Would you rather be too emotional or feel nothing?
225. Overdo and regret or underdo and regret?
226. Would you rather believe in miracles or believe in logic when you desperately need a miracle?
227. Be stuck for a year with someone who talks too little or with someone who talks just too much?
228. Would you rather play a luck game or a skill game?
229. Live at a place that always has morning or at a place that always has night?
230. If you have a chance to make a wish, would you let your past self do it or let your future self do it?
231. Would you rather go vegan for life or give up alcohol for life?
232. Give bad advice to your best friend or take bad advice from them?
233. Would you rather visibly blush every time you meet someone or burp every time you are about to kiss?
234. Kill someone innocent or be killed by someone else?
235. Would you rather be homeless or insane?
236. Stay away from trouble and let wrong happen or stand for the right and step the axe?
237. Would you rather die now or would you be immortal, seeing everyone dying one by one?
238. Be a part of an interesting rumor or start a rumor?
239. Would you rather apologize for something you haven’t done to sort out things or get punished severely for something you haven’t done?
240. Always feel overwhelmed or always be uninterested?
Difficult Would You Rather Questions about Career and Money
Money and career are some of the most crucial things for ordinary people. Because no matter what we do, we need to survive.
At the same time, everyone can have different perspectives on the very same thing. These hard questions give you difficult choices that would show your perspective about the same. Let’s explore –
241. Get an opportunity to do your dream job all your life or compulsorily no need to work at all for your living?
242. Would you spend all your youth working overtime or spend the rest of your life working normally?
243. 10 million dollars in your account but a life of 10 more years only or a normal life with a long life span – what would you choose?
244. Would you rather do your dream job for just a basic income or earn a lot doing a job you hate?
245. Have a horrible first impression that turns good with time or a great first impression but seems average later on?
246. Would you rather work hard for good money but without credit or for modest money but with the credit you deserve?
247. Be a specialist in one field or a jack of all trades?
248. Would you rather have the ability of multitasking or would you be double productive of what you are at present?/
249. Be close to your co-workers and have an okay relationship with your boss or a good relationship with your boss but a terrible equation with your co-workers?
250. Would you rather work 16 hours a day on your hustle or 10 hours a day on someone else’s?
251. Always be 20 minutes late at work or be 2 hours early?
252. Would you rather go to jail for 5 years and receive 1 billion dollars or lead a normal life without money?
253. Have to pay back your student loan or your credit card debt – what would you choose?
254. Would you rather spend much more than you should or save a lot and lead a below-average life?
255. Rather invest your money in your friend’s venture or invest it in bitcoin?
256. Would you rather do the same job for the rest of your career or necessarily change jobs every few months?
257. Have a lot of free time with a modest income or have a lot of money with no free time?
258. Would you manage all your finances by yourself or let Warren Buffet do it for you but without sharing any detail with you?
259. Go over your budget to make your family happy or stick to your budget no matter what for everyone’s financial safety?
260. Suppose your friend comes to you for significant financial help. You have the money invested in various forms. Would you rather take out your money from all investments or refuse your friend?
A little fun is always better. Especially, when things are already spicy with these hard questions, the funny ones are like adding a spoonful of butter to it.
So expect a lot of giggles, smirks, cringe, and facepalm moments. Are you up for some fun? Let’s dive into it!
261. Would you rather have one fingerless or 5 toes more?
262. Eat a cup of raw garlic paste or feed your boss something awful?
263. Would you rather mistake your neighbor for a criminal or mistake a criminal for your neighbor?
264. Be in superhero attire anywhere you go for a year or dress like a clown on every date for your life?
265. Would you always talk in tongue twisters or swear once in every conversation?
266. Dance every time you feel happy or sing every time you are sad, no matter where you are?
267. Would you rather spend a weekend with a nosy coworker or a rude relative?
268. Announce every time you feel bored in a meeting or doze off every time it’s your turn to speak?
269. Would you rather act like a baby in front of your crush or act like a flirt in front of your family members?
270. Never get anything free or always buy only from the thrift market?
271. Would you rather have everyone gossip about you or be someone no one ever notices?
272. Never be able to share yourself or always overshare?
273. Would you rather always wear clothes that were trendy 50 years ago or ones that would be trendy in the next 50 years?
274. Always have terrible haircuts or go bald instead?
275. Would you rather sound dumb or be dumb in real life?
276. Have a sandwich made with ingredients that taste terrible together or with the right ingredients but made by someone who can make anything taste terrible?
277. Would you rather have only one eyebrow or mustache only on one side? Okay, this is gender-neutral, to inform you.
278. Have a great body or free food?
279. Would you rather always wear wet socks or always wear wet gloves?
280. Always get lost on your way home or share your room with a ‘Karen’?
Can you play dirty? Like, spicy kind of dirty. Well, it’s a great time to learn it, if not. Because dirty banter is super fun, quite engaging, and a perfect call for a great time.
Of course, you need to make sure that you’re asking these depending on the situation and not throwing it on the faces of someone you barely know. That check, let’s explore!
281. Spending the whole day with your crush or the whole night?
282. Would you rather never get drunk or never feel orgasm?
283. Send your nudes to the company email or have a night-stand with your boss?
284. Would you rather wake up in your ex’s bed or in your neighbor’s?
285. Sleep in the middle of sex or burp in the middle of a kiss every time?
286. Would you rather have a limited number of kisses allowed in a year or a limited time of sex in the year?
287. Give up cursing forever or give up porn forever – what would you choose?
288. Would you rather have a passionate kiss with someone not interested in you or with someone you are not interested in?
289. Go to your workplace with a visible hickey or kiss your partner in front of all your coworkers?
290. Always sneeze before a kiss or always fart before a hug?
291. Would you rather get tired visiting a faraway exotic location to have your honeymoon or would you do it relaxed in a motel?
292. Always wear torn outfits or always be in dirty clothes?
293. Would you rather have an okay long-term relationship or a steamy short affair?
294. Kiss your crush for 1 dollar or kiss a stranger for 100?
295. Would you rather make out with a new stranger every day or never make out?
296. Have fingers in the place of nipples or nipples in the place of fingers?
297. Would you rather mistakenly send a sexy joke to your colleague or kiss your friend by mistake?
298. Receive a sexy cute message from a stranger or go on a date with your neighbor?
299. Would you rather eat oranges that taste like mud than mud that tastes like oranges?
300. Work at a strip club or go to your work dressed like a worker in a strip club?
Deep Would You Rather Questions
No matter what we say, secretly we all crave some deep moments. Like, an ease in conversation and topics w
301. Would you rather spend all your life surrounded and influenced by too many people or be alone and practice solitude all your life?
302. Take one leap of faith to risk everything now or regret all your life – what’s your choice?
303. Would you rather lose the ability to cry or lose the ability to smile? Let’s take a moment.
304. Understand others’ emotions but not able to show that you understood or not able to understand them but seem like you do?
305. Would you rather live in a world without any politics or live in a world full of politics where you are a successful politician?
306. Be poor yet happy or rich but unhappy?
307. Would you rather have less money but more love or love more but less money?
308. Be the predator or be the victim – what would you choose? Rather dark, indeed.
309. Would you rather live in a world where there are no arts or one without science?
310. Have the ability to make anyone smile or to make anyone cry?
311. Would you rather be completely open emotionally to someone and be vulnerable or never open to anyone at all?
312. Always daydream or never able to imagine things – what would you choose?
313. Would you rather misunderstand someone very close to you or be misunderstood by them?
314. Know everything about the outer world or know everything about your inner self?
315. Would you rather always sleep under a starry sky or always spend your evenings on the beach?
316. Be a hero who is considered a villain by everyone or a villain who is considered a hero by everyone?
317. Would you rather have a drunk talk with a close friend or a late-night talk with a stranger?
318. Have a successful life or a meaningful life?
319. Would you rather lose the ability to empathize or never be able to win an argument?
320. Have a conversation dumb to the verge of frustrating or too intellectual for you to understand?
Weird Hard Would You Rather Questions
How quirky are you? Well, we all have our quirky sides. If yours is yet to be explored, these cool hard weird questions are the perfect prompt.
And if you’re already into weird things, you’ll love these questions. Quick tip – be ready to receive some weird expressions while you ask these questions.
321. Be an attractive jerk or an unattractive good person?
322. Would you rather always forget to brush your teeth or never forget your most embarrassing moments?
323. Fight with a chicken every time you leave home for work or pet an alligator every time you return home?
324. Would you rather fart loudly on a romantic date or in a job interview?
325. Always start your conversation with a rude remark or always end it with a cheesy one?
326. Would you rather have rotated elbows or rotated knees?
327. Always sing loudly when poop or always snore loudly when sleep?
328. Would you rather smell like cheese or feel like jelly?
329. Bite your tongue to blood or strike your little toe on the wall? Well, both are painful.
330. Would you rather have a weirdly big nose or crazy tiny teeth?
331. Never sit comfortably or always trip before standing?
332. Would you rather sneeze non-stop for an hour or hiccup continuously for 12 hours?
333. Have a phobia of good food or a phobia of beautiful people?
334. Would you rather be omniscient or omnipresent?
335. Be a rock or have to take a rock with you everywhere you go?
336. Would you rather give up all sweet things or only eat sweet things?
337. Like to know who would you marry in future or what job would you do in future?
338. Would you rather wake up as a person with a different life but the same or a person with a different face but the same life?
339. Have a ring stuck in your finger or a choker stuck in your neck?
340. Would you rather always whisper on a date or always shout in an interview?
Hard Would You Rather Questions to Ask Yourself
We all ask questions – from a stranger at a party, your partner, colleagues, to any random person but yourself.
Yes, when was the last time you asked yourself a question? Ask some today. These
341. Would you be by your side if you do something wrong unintentionally or would you blame yourself?
342. If you had a chance, would you make better decisions in the past or make the right moves in the future?
343. Would you rather have a higher IQ or higher EQ, if you had to choose one?
344. If depressed, would you rather talk to someone or bear it yourself?
345. Would you choose your spiritual growth or financial growth if you had to choose one, basics provided?
346. Love someone more than they love you or be loved more than you do?
347. Spend all your life in the lap of nature with basic facilities or away from nature with the latest technology and luxury?
348. Would you rather have one good friend or many casual ones?
349. If something happens in life, would you do what you want to or what you should do?
350. Live the best life today or sacrifice today in making life better tomorrow?
Here, our list of amazing hard would you rather questions is done. Most probably, you already are into it. Still, if you need something to be convinced that this is not a complete waste of time, here’s all you need –
Benefits of Asking Would You Rather Questions
Here are some of the benefits of would you rather questions apart from the usual entertainment value it adds to everything –
- Can make for interesting conversations.
- Great way to pass the time. Especially, when you don’t have something else to do.
- An easy way to get to know someone without asking personal questions.
- Adds new perspectives and dimensions.
- Great way to socialize.
- Boosts critical thinking and quick decision-making skills.
- A good communication exercise promoting active listening and speaking.
The Wrapping Up
Now, you’ve got everything you want for a perfect conversation. Some great ‘would you rather questions to ask’, interest in it as you’re here, and any situation that needs some fun added.
Be confident, enjoy the conversation, and rock it!
That one person in the room who is always with a book and gets excited when it's time for some small-deep conversations - that's Kirtika. She loves words, Arts, Psychology, and everything that asks for her creative self. If you smiled more, even a bit, after coming here at ThePleasantConversation, chances are high, she'd be glad!