300+ Best This or That Questions For Great Conversations

Sharing is caring!

This post may contain affiliate links, meaning if you book or buy something through one of these links, I may earn an affiliate commission at no additional cost to you. Learn more

Spark plenty of intrigue and meaningful interaction into future conversations with these creative and thoughtful this or that questions, be it with friends, partners, family, or strangers.

Best This or That Questions

Best This or That Questions (14 of the questions listed below).


No matter who’re you chatting with, these good this or that questions can help kickstart some healthy conversation and debate.

1. Spend your money or save your money?

2. Work as a team or work individually? 

3. Skip a meal or lose two hours of sleep? 

4. Travel back in time to Ancient Greece or Ancient Rome?

5. Glass half empty or glass half full?

6. Have one incredible talent or be quite good at everything?

7. Be a celebrity or a regular person?

8. The perfect job or the perfect relationship?

9. Work a different job every week or be stuck in your current job for 5 more years?

10. Swimming pool or hot tub?

11. Do the laundry or wash the dishes?

12. Speak to animals or speak all foreign languages?

13. Superheroes or supervillains?

14. Give a gift or receive a gift?

15. Be a politician or a journalist?

16. Beach holiday or ski resort?

17. Give a ride to a hitchhiker or hitchhike yourself?

18. Girl friends or guy friends? 

19. Booksmart or streetwise?

20. Sight or sound?

21. Ticket to see your favorite band or favorite sports team?

22. Drive or be driven?

23. Disney World or Universal Studios? 

24. Go backpacking or stay in luxury hotels?


Want to keep things light-hearted and enjoyable? Throw some of these fun questions into conversations with friends, family, and people you have just met.

25. Singing or dancing?

26. Go for a run or go for a hike?

27. Team sports or work out alone?

28. Winter or summer?

29. Spring or autumn?

30. Comedies or thrillers?

31. Be the host or go to somebody else’s house? 

32. Travel around Europe or travel around Asia?

33. New haircut or new clothes?

34. Date a famous businessperson or famous singer?

35. Friday or Saturday?

36. Aliens or zombies?

37. Time machine or teleportation device?

38. Hogwarts or Middle Earth?

39. Give up social media or give up access to all other websites?

40. Brand new phone or brand new laptop?

41. Art festival or music festival?

42. New house or new car?

43. Headphones or speakers?

44. Go out to a restaurant or go to a bar?

45. Batman or Superman?

46. Beyoncé or Rihanna?


Ensure plenty of snorts, giggles, and laughter by asking whoever you’re chatting with some of these funny this or that questions.

47. Work hard or hardly work?

48. Never be able to tell a lie or everybody has access to your browsing history?

49. Live for a week without the internet or without a shower?

50. Shave your eyebrows or have a monobrow?

51. Turn into a vampire or a werewolf?

52. Fight one horse-sized rat or 100 rat-sized horses?

53. Forgive and forget or hold a grudge?

54. Tell the truth at all times or everybody else tells you the truth?

55. Have no hair at all or be covered in hair?

56. Live the life of a dog or live the life of a cat?

57. No toothpaste for a week or no deodorant for a week?

58. Water fight or food fight?

59. Cry too easily or laugh too easily?

60. Finish an assignment immediately or procrastinate for days?

61. Turn up to an event incredibly overdressed or underdressed?

62. Sweat mayonnaise or sweat tomato ketchup?

63. Paper cut or nettle sting? 

64. Have one finger less or an extra finger?

65. Spend 10 minutes cuddling puppies or kittens?

66. Feel constantly itchy or constantly sticky? 

67. Eat a tiny but delicious sandwich or a mediocre but filling sandwich?

68. No hot water or no internet?

69. Always forget your own name or always forget everyone else’s?

70. Be stuck in a lift alone or with your ex?

71. Sunburn or beesting?

72. Three arms or three legs?

73. Never be stuck in traffic again or never be stuck in a queue again?

74. Super-sensitive tastebuds or super-sensitive hearing?

75. Travel to the moon or travel to Mars?

76. Lose your passport or your driving license?

77. Be an only child or have ten siblings?

78. Have someone read your diary or your text messages?

Interesting and Unique

You’re sure to put a few fingers to chins and tax a few minds by asking some of these interesting and unique questions when you’re next in a conversation.

79. The ability to fly or the ability to read minds?

80. The ability to understand any language or the ability to play any instrument?

81. Give up your past memories or never make new ones?

82. Receive a lump sum of 50 million dollars or one million dollars every year for the rest of your life?

83. Travel to the future or travel to the past?

84. Be in the Harry Potter or Game of Thrones universe?

85. Travel the world or build your career?

86. Work hard and retire early or work a regular week and retire at 65?

87. The power of invisibility or the power to time travel?

88. Streaming platform or record player?

89. Ticket to the Oscars or ticket to the Emmys?

90. Underwater or up in the air?

91. Skydiving or bungee jumping?

92. A month without seeing friends or a month without seeing family?

93. Tattoos or piercings?

94. Live in a hut on the beach or a cabin in the woods?

95. Super-sensitive hearing or super-sensitive tastebuds?

96. Countryside mansion or city center penthouse? 

97. Be talented or well-liked?

98. Live on a boat or live in a treehouse?

99. Stay where you live now forever or move country every year?

100. Never need to sleep or never need to eat?

101. Owe someone money or owe someone a favor?

102. Stranded in the Amazon rainforest or stranded in the Sahara desert?

103. Have your favorite celebrity over for dinner or have your celebrity crush ask you on a date?

104. Be a witch or a wizard?

105. Christmas every day or your birthday every day?


Nervous about striking up a conversation with strangers or on a first date? Have some of these icebreaker this or that questions in your back pocket to get things going.

106. Smartphone or laptop?

107. Work in the office or work from home?

108. Dogs or cats?

109. Dress smart or dress casual?

110. More money or more time?

111. Harry Potter or Lord of the Rings?

112. Morning or evening?

113. Play sports or watch sports?

114. Hand out with a group or hang out one-on-one?

115. Trip or staycation?

116. Bowling alley or roller rink?

117. Christmas or Halloween?

118. Reality TV shows or documentaries?

119. Play it safe or take risks?

120. Stay busy or have lots of free time?

121. Learn a new language or learn a new instrument?

122. Shoes or slippers?

123. Driver or passenger?

124. Sunshine or snow?

125. Weekends or weekdays?

126. Iced coffee or hot coffee?

127. Pop music or rock music?

128. Multi-task or do one thing at a time?

129. Sun or moon?

To Get to Know Someone

Want to go behind light-hearted and trivial topics with someone you’re building a connection with? These questions are great to use to get to know someone better.

130. Night owl or early bird?

131. Work to live or live to work?

132. Facebook or Twitter?

133. Text message or phone call?

134. A few best friends or lots of acquaintances?

135. Work fewer days but for longer hours each day or work a standard 5-day week? 

136. Night out at a bar or night in watching movies?

137. Poetry or novels?

138. Better salary or better work-life balance?

139. Buy a sports car or have a personal driver?

140. Inherit all your money or start your own business?

141. Makeup or bare-faced?

142. Handmade gifts or luxury gifts?

143. Fix it yourself or hire a professional?

144. City or countryside?

145. Terrible job with a great boss or great job with a terrible boss?

146. East Coast or West Coast?

147. Pebble or sand beach? 

148. Have perfect teeth or perfect hair?

149. Gold or silver?

150. Lions or tigers?

151. Win a race or win a debate?

152. Spend time alone or with people you don’t like?

153. Plan ahead or wing it?


Chatting to a fellow foodie, or just want to bring the topic of food into the conversation? Try some of these food-related questions.

154. Small plates or a meal all to yourself?

155. Indian or Chinese takeaway?

156. Pizza or pasta?

157. Peanut butter or jelly?

158. Fruit or vegetables?

159. Sandwich or burger?

160. Mcdonald’s or Burger King?

161. Ice cream or cookies?

162. Coffee or tea?

163. Breakfast or dinner?

164. Dark chocolate or white chocolate?

165. Bacon or sausages?

166. Spicy or mild?

167. Sweet or savory?

168. Starter and main or main and dessert?

169. Sugar or salt?

170. Crisps or chocolate?

171. Eat two big meals a day or five small ones?

172. Orange juice or apple juice? 

173. Go out for dinner or cook at home?

174. Toast or a bagel?

175. Pasta or rice?

176. Spaghetti bolognese or lasagne? 

177. Meat option or vegetarian option?

178. Eat at a restaurant or order a takeaway?

179. Beer or wine?

180. Never eat meat again or never eat vegetables again?

181. Hot drinks or cold drinks?

182. Food too spicy or too bland?

183. Apples or oranges?

184. Garlic or onions?

185. Eat more at breakfast or eat more at lunch?

186. Coffee at home or at a coffee shop?

187. French fries or onion rings?

188. Pancakes or waffles?

189. Guacamole or salsa?

190. Cappuccino or latte?

191. Thin crust or deep pan pizza?

192. Ice cream in a cone or a cup?

193. Salad or soup?

194. Sauce on the side or sauce on top?

195. Frappucino or mocha?


Find out about someone’s hobbies and interests, and see if you can find common ground, by asking some of these activities-related questions when talking to someone.

196. Art gallery or history museum?

197. Beach holiday or sightseeing city break?

198. Binge-watch a Netflix series or head to the cinema?

199. Refreshing shower or relaxing bath?

200. Cardio workout or weight lifting?

201. Yoga class or run in the park?

202. Rom-com or horror movie?

203. Reading or listening to music?

204. Swim in a pool or in the sea?

205. Saturday morning hike or Saturday morning lie-in?

206. Out for brunch or out for dinner?

207. Rock climbing or mountain biking?

208. Night out at karaoke or pizza party at home?

209. Summer sports or winter sports?

210. Listen to music or listen to a podcast?

211. Spend time with friends or spend time with family?

212. Afternoon at the park or afternoon playing video games?

213. Hike in the mountains or play volleyball at the beach?

214. Read or write?

215. Keep a journal or meditate?

216. Give up music or TV? 

217. Comedy show or night at the theatre?

218. In-person meetings or video calls?

219. Card games or board games?

220. Theme park or water park?

221. Skiing or surfing?

222. Shopping online or shopping in person?

223. Arctic or desert?

224. Piano or guitar?

Flirty/For Couples

Help things get a little more heated with a date or partner by asking some of these flirty questions to each other, and let the intimacy intensify.

225. Breakfast in bed or romantic dinner?

226. Hugs or kisses?

227. Dating app or blind date?

228. Good morning or good night text?

229. Spend the day together or spend the night together?

230. Go on a day trip together or visit the spa?

231. Holding hands or snuggling on the sofa?

232. Make the first move or be asked out first?

233. Have a wedding with all your friends and family or elope?

234. Get married in a church or in a castle?

235. Watch a movie or watch the sunset?

236. Pay for a meal or have your partner pay for you?

237. Receive a surprise gift or have dinner cooked for you?

238. Share food or separate meals?

239. Present or experiences for your birthday?

240. Chocolate fondue or strawberries and cream?

241. Go out for date night or have date night at home?

242. Left or right side of the bed?

243. Five kids or no kids?

244. Long walk in nature or cuddles in front of the TV?

245. Stay-at-home parent or breadwinner?

246. Know everything about your partner’s past or know nothing about your partner’s life?

247. Affection or gifts?

248. Be spontaneous or make plans?

249. Give compliments or receive compliments?

250. Love at first sight or love that develops over time?

251. Plan the future or enjoy the present?

252. Massage or pillow fight?

253. Talk it out or give the silent treatment?

254. Never be able to hug again or never be able to kiss again?

Deep, Thought-Provoking, and Philosophical

Connect with someone on a truly deep level and go far beyond trivial topics by asking some of these thought-provoking and philosophical questions.

255. A life full of ups and downs or a more stable life with less excitement? 

256. A successful career or successful family life?

257. Lots of money or lots of friends?

258. Be the heartbreaker or have your heart broken?

259. Be an extrovert or an introvert?

260. Run a country or run a business?

261. Stability or living outside the box?

262. Be extremely lucky or extremely smart?

263. The ability to meet your ancestors or the ability to meet your great-grandchildren?

264. Recognition or money?

265. Overprotective parents or disinterested parents?

266. Spend time with animals or spend time with strangers?

267. Brutal honesty or white lies?

268. Be rich doing something you hate or be poor doing something you love?

269. Be famous while you’re alive or leave a posthumous legacy?

More Questions

Still looking for great this or that questions to ask a wide range of different people? These random questions should give you both plenty to ponder, discuss, and connect over.

270. Follow the recipe or make your own?

271. Spend time indoors or spend time outdoors?

272. New York City or Los Angeles?

273. Spend your money on travel or buy a nice house?

274. Study or work?

275. Music from the 80s or music from the 90s?

276. Snakes or insects?

277. Life before the internet or life with the internet?

278. Never use your phone again or never watch TV again?  

279. London or Paris?

280. Be born in 1950 or 1050?

281. Run your own business or work for somebody else?

282. Board games or video games?

283. Games of strategy or games of luck?

284. Speak Spanish or speak Mandarin?

285. Lots of children or lots of pets?

286. Clean the house or cook dinner?

287. Work early and finish early or start late and finish late?

288. Sunrise or sunset?

289. Weather that is too cold or too hot?

290. Bar of soap or shower gel?

291. Halloween party or scary movie at home?

292. Zoo or aquarium?

293. Drive an ambulance or drive a school bus?

294. Dress in black and white or colors?

295. Sort by price or rating?

296. Free coffee or free snacks? 

297. Ending with a resolution or cliffhanger?

298. Long hair or short hair?

299. Air conditioner or windows open?

300. Brunch or summer picnic?

301. Date night or girls’ night / guys night?

There are so many ways to keep the conversation fresh, interesting, and flowing, and these this or that questions are great to ask in many different situations.

Be it on a date, with a close friend, or with a group of people, memorize a few of them, and use them to take the conversation in unusual and exciting directions.

You Might Also Like to Read

Keep these this or that questions for safekeeping by saving this article to one of your Pinterest boards.

Best This or That Questions (14 of the questions listed above).