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650+ Interesting Questions to Ask for Engaging Conversation

650+ Interesting Questions to Ask for Engaging Conversation

Updated on May 17, 2022 | Published on September 21, 2021
Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling), Life & Relationship Coach
650+ Interesting Questions to Ask for Engaging Conversation

Making statements is not always important for having good conversations. Sometimes, there are interesting questions to ask in any boring and stifling conversation to keep it engaging and effective.

There are various questions that you can ask and these vary with the circumstance, event, and the environment which need specific answers.

A good question, on the other hand, can be the difference between a lengthy and predictable night and a fantastic and fruitful meeting of minds.

So, if you want to be the most intriguing person in the room, ask the most engaging and pick up line questions that will lead to enthralling talks.

Interesting questions can be categorized into valuable, funny, romantic, starters and spark up questions to ask in a boring gathering.

Therefore, let’s deep dive into the broad list of interesting questions to ask boy, girl or anyone.

650+ Interesting Questions to Ask for Engaging Conversation
650+ Interesting Questions to Ask for Engaging Conversation

Interesting questions to ask a guy

In conversation with a guy, it’s quite difficult to ask the right, insightful and fun questions. Since you don’t know what can interest him and what not, any random question can destroy your pleasurable conversation experience.

Therefore, here we have curated a list of deep questions to ask a guy to start a conversation.

1. What is a thing in your life that brings a smile to your face no matter how upset or sad you are for any reason?

2. Which one is your favorite movie that you watch over and over again but never get fed up with or irritated?

3. Would you like to share your one deepest secret that you have never ever shared with your best friend or close one?

4. If you are asked to leave your country and opt for another one, then which two countries will you opt from?

5. Are you an animal lover? If yes, then would you like to take a pig as your pet?

6. To whom do you go for consolation and sometimes advice when you are feeling low and stuck in any problem or critical situation of life?

7. If you are asked to choose only one meal for your entire life to eat then which one would you like to eat?

8. Does passion mean a lot in your life? If yes, then what is the one important thing in your life which you are more passionate about.

9. Which one of the senses in your body you think you need the least and you don’t mind losing it if in any case you have to lose one of your senses?

10. Do you think that you made the hardest decision in your life which was not easy but you have to make it for the sake of going ahead?

11. Which one physical activity you were engaged in but regret doing and now decided to never do again because the experience was not joyful?

12. How many jobs have you done since you graduated from college and how was the experience of doing those jobs in positive and negative aspects?

13. Have you ever compared your character with any wild animal? And if you do so then which wild animal is it?

14. Can you tell three words that you think will best describe your character and personality?

15. Which country do you think that it’s the coolest nation and you are willing to visit there very soon?

16. What attracts you most to the opposite gender? Is it personality, body features, talent, voice or smile?

17. What characteristics of girls do you think are a turn off to most guys?

18. According to you, what’s the sweetest thing that you ever did with a lady and she found it pleasing and exciting?

19. Which is your favorite pub in the town and why do you like to visit it often?

20. What do you think can make an ideal and memorable date? Is it the environment, decoration, gifts, surprise or anything else?

21. Who do you think has given you the best ever compliment and you will never forget it? 

22. Do you love cooking food? If yes, then what would you like to cook often and enjoy making it.

23. Do you have any long term goals? What would you like to achieve in the next 5 years?

24. Which one decision in your life that you made changed your life for the better reason and you are proud of making it?

25. Which one do you think is your guilty pleasure? Is it drink, snack or junk food?

26. If you are asked to eat junk food for the rest of your life then which three fast foods would you choose?

27. If you find an opportunity to start your life once again, are you able to go back to your mother’s womb?

28. Which things do you find consistent about the ladies whom you have dated so far?

29. Which one is your childhood toy you like the most and you still have it as well as play with it often to memorize the childhood days?

Interesting questions to ask a girl

Girls love good sense of humor and fun! Not only for conversation but also in every aspect of life. In order to keep a girl engaged and interested in your conversation for long hours, these are interesting questions to ask a girl.

This will make you understand what she thinks and what she wants. Let’s take a look at conversation starter

30. If you will ever have a chance to change your job or career then what could be your dream job?

31. What would you like to tell the world if it was listening to you right now?

32. How have your past relationships gone? Do you have any heart breaks?

33. What would be your reaction or what would you do first if I faint out right now?

34. Which of your favourite sea creatures do you wish you could be if you were one?

35. Do you like to read books? If so, who is your favourite author and what kind of personality you like?

36. Consider what life would be like if we only had three choices: freedom, fame, and money. Which would you pick, and why?

37. Who would you like to have lunch within Hollywood if you get a chance?

38. What is the optimal height for your perfect partner in your opinion?

39. Who would you want to be if you were to come back from the dead?

40. I’m just interested to know whether you go out frequently or you like to stay home often. If yes, then why?

41. What do you want to carry if you get an opportunity to carry one thing with you after death? 

42. If it is possible, then what would you like to be a donkey or money?

43. If you get a voucher for 20000 what would you like to buy with that money and how will you spend it within 24 hours? Your wishlist item, household items or something for your loved ones?

44. Which male and female celebrity do you have a crush on? And which celebrity do you hate the most or don’t want to see him/her?

45. If your long distance best friend just visited your country then which favourite food could you cook for your friends as a surprise?

46. If you gave birth to a physically challenged child then what would be your reaction at that time?

47. Which one famous celebrity or person do you wish he/she would not have died? 

48. If you get to know that if you have only 6 months remaining in this world then what value would you like to give to this world?

49. If you win the lottery of one million dollars luckily then how do you think that it will be able to change your life completely?

50. Which country are you willing to visit even if you get the facilities of free ticket and accommodation in a five star rating hotel?

51. According to you, which is the best age to get married and have kids for a man as well as for a woman?

52. What is your thought about having numbers of kids that can make your life complete and happier? Or simply, how many kids do you want to have in your life?

53. I am just curious to know what is the most embarrassing moment that has ever happened in your life and why?

54. Do you remember the first time you visited a cinema hall? How old are you when you visit there for the first time and with whom?

Interesting questions to ask people

Asking someone about their favorite things and hobbies is a great way to get to know them better and understand their opinions and preferences.

When you meet a person for the very first time, these interesting questions can leave a memorable impact on their mind. You can even ask these questions to anyone, be your friend, family or colleagues to pass the time.

55. What is the best memory of your childhood that is close to your heart even today?

56. If you get a chance for a do-over in life, what would you like to be different from others?

57. If you get an opportunity to live anywhere in the world, then which place would you like to visit and why?

58. If you can only keep five possessions in your life then what will they be?

59. Which teacher in your school has made the most impact on you and why is it so?

60. What was the most defining moment in your life and close to your heart? And why?

61. What do you do in your spare time? Do you watch TV, play any sport, listen to music or something else?

62. Why did you choose this profession as your career and how is it going on?

63. Do you love to read books? Then, what are your top three favorite books and why do you like them?

64. What’s your biggest fear in life that you are most afraid of doing or experiencing?

65. What’s your love language? The words, behavior and attitude that make your partner feel loved and how you express love?

66. What’s your biggest strength and weakness in life and why are they?

67. I’m just curious to know about your most embarrassing moment in life that still makes you laugh?

68. If you will be a president, what’s the first thing that you will do for country and citizens?

69. If you get a chance to witness the events of the past, present or future then what would you like to witness?

70. Are you interested in learning any new and exciting skills? Then what would you like to learn or explore?

71. According to you, what does a perfect date mean to you and what do you expect on the date?

72. Have you ever broken the law? Then what’s the funniest way of breaking it?

73. If you were given a choice to throw one thing from your life then what would you choose? Love or money?

74. If you get suddenly transferred to another planet then how would you react and assess the situation?

75. If you could only choose a word for the rest of your life to speak then what would you like to choose?

76. If you were given an elephant but you can’t ride on it then what would you like to do with that giant animal?

77. What is your favourite song that you would like to play right now if I asked? And why like that song? 

78. What’s the strangest thing that you encounter and fall in love with immediately? And why? 

79. When did you meet the stranger last time and you have thought to never meet him again in your life? 

Interesting questions to ask someone

Meeting someone is an easy task but understanding their thoughts and life choices is not that easy.

Therefore, asking someone about their preference helps you to understand who they are as a person. Go deeper by asking the follow up questions and keep them engaged with your group of good questions.

80. If you can throw a party for any special event then what would it be like and what would it be for? And do you like to enjoy parties?

81. If you were able to paint a picture of the scenery that you have viewed recently or a long time ago, what would you like to paint? Share your creative thoughts!

82. If you can opt for living a particular age for the whole of your life then what would it be? Childhood, adult or old age?

83. If you get to know that the world will end in 2022, then what would you do differently?

84. If you get a chance to choose someone as your mentor for guidance then whom would you like to choose to go ahead?

85. If you can witness any event in your life of past, present or future then what would you be?

86. If you get a chance to learn anything in your life then what would you like to learn and execute?

87. Which project would you choose if you get the chance to work on only one project for the next two years?

88. What will you do or how will you react if you will be immortal for a whole day?

89. When you get a chance to meet someone be your friend, partner or loved one who is dead or alive then whom would you like to meet?

90. If you won a lottery ticket of high price then what would you do first with that money and how would you spend the whole money?

91. When you get free time of exactly 50 minutes then how would you like to spend it? And what do you do in your spare time?

92. In future, if you get the chance of writing your autobiography then what would you like to name the autobiography of your life?

93. What was your dream and what do you want to become in your life when you grow up?

94. Has this ever happened to you that you thought was bad but eventually it turned out to be best and lucky for you?

95. What animal, drink, or ice cream flavour would you be if you were reborn as?

96. What would you ask if you could know the answer to any question other than “What is the meaning of life?”

97. Who would you want to be if you could be any literary character?

98. When you were a kid, what was your favourite food? Homemade, school lunch or chocolates?

99. What is the music on your iPod that you listen to the most while travelling or doing anything which gives peace to your mind?

100. What is a favourite quote of yours that you have created or got inspired from?

101. Which of the following activities do you enjoy doing both indoors and outdoors? Gaming, reading, watching video or anything else?

102. What chore do you dislike doing or having the most?

103. What is your preferred method of exercise in the morning?

104. What is your favourite time of day, weekday, month, and year when you enjoy doing things and find luck for yourself?

105. Which mode of transportation is your least favourite that you found troublesome or inconvenient when travelling or going to work?

106. What is your favourite portion of your body that you often appreciate and gaze at? Weird, right!

107. What was the last TV show, movie or reality show that you watched and went up into tears eventually?

Interesting questions to ask friends

We all have friends who are known forever. Some are those who bring snacks and arrange a perfect Netflix night and some are those with whom the conversation can continue the whole night.

Here are some of the questions that help to understand your besties even better and spice up the conversation as well.

108. Are you curious to know about which body language suits you?

109. What is the one emotion in your life that you feel and experience the most?

110. When you first saw me, what was your first experience and what do you think about me?

111. If you get pressurized to open a bar or lounge then will you like to go ahead? If yes, then what would you name that and why did you choose that name?

112. If we both go to jail together for any crime then what would it be for?

113. If you are able to learn the date and time of your health then would you like to learn it and why?

114. What is the most embarrassing thing that you have done in your life and why?

115. Have you ever shoplifted and if you do that then what did you take?

116. On visiting a deserted island what are the 4 essential things that you would like to carry with you?

117. What’s your one childhood fear that you have never told anyone till now? 

118. Do you have any secret obsession which I don’t know? Tell me?

119. If you get a chance to do anything for your entire life then what is the one thing that you would like to do?

120. What makes you feel super loved and cared for? And why would you like that?

121. What is the one thing that you lie most about in your life with your friends, family or even strangers?

122. What is the silliest thing that you have done and gotten upset about it?

123. What is your least favourite celebrity and most favorable celebrity?

124. If you get a chance to re-do one day of your life then what would you choose and why?

125. What is your most favourite viral video and why do you like it?

126. If you could be able to control the time or be able to know what people are thinking then would you like to choose from both?

127. If you found $2,000 on the ground then would you pick up that money and how would you like to spend it?

128. What would you like to do if you can control the activities and abilities of your dog? 

129. What is the smartest thing that you have done so far and why do you think that it’s your smartest act?

130. Do you like eating pizza? What is your favourite pizza topping and why would you like that?

131. Do you like to take a stand for yourself for the right things or do you just let things go no matter what?

132. What’s your worst habit and how are you improving it with the right efforts and solutions?

133. Have you ever been stuck in traffic? Then how much traffic affects your mood to get spoiled?

Interesting trivia questions

Do you want to play trivia with your friends or family members? Then you surely need these questions.

This creates the bonding of lifetime and tests your general knowledge skills as well. Have these questions and prepare the list and get ready to play and win.

134. What is that one thing which usually comes down but never goes up again?

135. What is a thing in everyone’s life that can be broken but is never held?

136. Who invented the word “vomit”?

137. What’s the illegal thing to do while wearing a swimsuit in public places in the state of Florida?

138. What’s the duel of three people called?

139. What’s illegal to eat with a fork in the state of Georgia?

140. Which tissue in our body connects the muscles with the bones?

141. How many teeth can an adult human being have? 

142. Is Pluto considered a planet? If not then why?

143. What is the color of your blood when it’s inside your body?

144. In 2004, what was discovered on the island of flores in Indonesia?

145. Which one of Newton’s laws says that “for every action there would be an equal reaction”?

146. In what type of matter the atoms get most tightly packed?

147. Can you tell me which is the hottest planet in the solar system?

148. Which country has the most natural lakes out there?

149. Riyadh is the capital of which middle-eastern country? 

150. Which central American country has a name which translates to the English as “The saviour”?

151. Which country touches the Indian Ocean, the bay of Bengal and the Arabian Sea?

152. The ancient Phoenician city of Constantine is located in what modern day Arab country?

153. Which country borders 14 nations and crosses 8 time zones?

154. Which country has the responsibility to create Olympic games?

155. In the poem of Humpty Dumpty, where did Humpty go when he fell?

156. “Stars and stripes’ ‘ is the nickname of the flag associated with which country?

157. Which mythical creature are you?

158. What is the name of the professional ice hockey team located in Toronto, Canada?

Interesting questions to ask your boyfriend

Do you want to know your boyfriend’s thoughts about you and his future plans? Then, these interesting questions as conversation starters related to both of your lives can make you understand him better and make your relationship stronger and healthier.

159. When you saw me for the very first time then what comes to your mind? 

160. What comes to your mind every time when we hug each other tightly?

161. What would you like me to do to spark up our relationship?

162. Will you be with me even in case of a long distance relationship and less communication?

163. If I get a job transfer to another country, will you come with me or stay in a long distance relationship?

164. When would you like to meet my parents and would you take me to meet your parents?

165. What is the first thing that comes to your mind when you see me lying on the bed each morning?

166. Where will you take me for our first vacation after we get married and why?

167. What do you think every time we are apart? Do you miss me?

168. Which date did you enjoy the most from all the dates we had till now?

169. Will you accept an offer from a lady when she wants to pay the bill at a restaurant on your first date?

170. Do you think that I am your soulmate and if yes then why do you find me as your soulmate?

171. If you get a chance then can you confess on the live TV show that you love me in front of everyone?

172. What caught your attention when you saw me for the first time and how can you explain it?

173. What is your biggest deal breaker in a relationship?

174. Do you like kissing in the rain or in public or in the dark? 

175. How would you like to kiss me? While closing your eyes or when your eyes are open?

176. What would you prefer more? Kissing for 10 seconds or hugging for 20 seconds straight?

177. Do you always feel comfortable when I hold your hands in public? 

178. Which one of exes do you hate the most for breaking your heart badly when you love intentionally?

179. What will you do to make me happy when I feel low or become upset?

180. If I could be an action character then which character would suit me well or would I be able to play it well?

181. What did you think about me when I recalled that I drink a lot?

182. Do you feel comfortable when you go out with your or my friends who are still single?

183. If I told you that “I do not love you anymore”, then what could be your reaction?

184. Where would you like to take me between a tropical vacation and camping?

Interesting questions to ask your girlfriend

If you want to understand the opinions of your girlfriend about you and your relationship then these good questions to ask a girl can help you understand her better. This way you will take your relationship to another level and make an unbreakable bond.

185. Where would you prefer to live, under a sea or between a cave and why?

186. If you would choose one person between me and your mother then whom would you like to choose?

187. When would you like to get married and in which country do you want our wedding to take place? 

188. Have you found it difficult to ask me for a date or go out with me?

189. According to you, what’s your definition of happy and lovely marriage?

190. If you get a chance to choose a supernatural power then what would you like to choose?

191. Which one is the dumbest question that you asked a boy or girl and why did you ask it?

192. When you were a child, what was your favourite cartoon that you loved to watch every time?

193. If your favourite actor will propose to you one day to get married, will you leave me for him?

194. What could be your reaction if I scold you in public?

195. Have you ever cheated on me? And according to you, what’s most likely to get cheated?

196. What is your recent favourite romantic movie or what is the most romantic movie that you ever watched?

197. Are you comfortable if I check your bag everytime or you don’t like it?

198. What would be your reaction if you got to know that I am cheating on you with my ex-girlfriend?

199. If you get a chance to solve the issue that led to the breakup with your Ex, will you take that chance?

200. According to you, what is the best thing that your parents incorporated in you and that has impacted your life for betterment?

201. How many times has your ex cheated on you? And how were you feeling each time when you caught her cheating?

202. Can you give your boyfriend a 2nd chance if you found that he is cheating on you?

203. Will you allow my girlfriend to sleep at our sleep when you are at home or out of the town but I am around?

204. Which is the worst advice that you think you ever got from a friend?

205. Do you have any passionate hobbies that you always want to do?

206. Do you like to have delicious exotic meals from a local hotel or a local fruit cake from a five star hotel? 

207. Can you think that your life will be at its worst for the next 5 years and why?

208. When do you think that you will be able to purchase your dream car and house?

209. Tell me one thing that always makes you happy and another thing that always makes you sad or emotional?

Interesting would you rather questions

It’s always fun to give someone two choices and ask them to choose one. Isn’t it? These interesting questions make family reunion conversation fun and exciting with the quiz kinda questions.

210. Would you rather go into the future to meet your great grandchildren or go into the past and meet your ancestors?

211. Would you rather go for a pause button or rewind button in your life?

212. Would you rather speak to animals or speak all foreign languages?

213. Would you rather feel bad if no one attended your wedding or no one showed up to your funeral?

214. Would you rather be without the internet for a week or without a phone for the same amount of time?

215. Would you rather work more hours per day but fewer days or work fewer hours per day but more days?

216. Would you rather say everything in your mind or never speak again?

217. Would you rather be the most popular person at work or school or the smartest?

218. Would you rather spend the night in a luxury hotel room or camping surrounded by beautiful scenery?

219. Would you rather like to explore space or the ocean?

220. Would you rather get stuck on an island alone or with someone who talks non stop like crazy?

221. Would you rather get rich through the winning of a lottery or through your hard work?

222. Would you rather have a 10 hour dinner with a headstrong politician from an opposing party or attend a 10 hour concert for a music group you like?

223. Would you rather be an Olympic gold medalist or a nobel prize winner?

224. Would you rather live at the top of the tall NYC apartment building or at the peak of a mountain?

225. Would you rather be proposed to in private or in front of family and friends?

226. Would you like to spend your whole day with your favourite sports person or your favourite celebrity?

227. Would you rather live where there is a constant summer season or where there is a constant winter season?

228. Would you rather want an unlimited gift certificate to a restaurant or a shopping store?

229. Would you rather be able to take back anything you say or hear every conversation around you?

230. Would you rather be the star player of a losing football team or ride the bench on a winning moment?

231. Would you rather have the best house in the worst neighborhood or the worst house in the best neighborhood?

232. Would you rather be an unknown major league basketball player or a famous badminton player?

233. Would you rather spend 20 years in prison and be released as innocent or be put away for five years and be considered guilty forever?

234. Would you rather take an action packed European vacation or spend two weeks at the same Caribbean resort forever?

Interesting interview questions

While taking an interview, finding out or understanding the individual’s potential and thought process can be possible by asking the right questions. So let’s have a look at these questions to ask in an interview round.

235. If I hire you for this role and I granted you three promises with regard to working here then what would they be?

236. What are your pet peeves?

237. What do you do in your free time? Would you follow your hobby or learn a skill?

238. How much do you give the value to the store which is located at the corner?

239. How can you describe yellow color to people who can’t see it? 

240. How would you feel if someone criticized your work and passed judgement?

241. Whom do you consider your role models or mentors to grow in your career life?

242. What are your favourite books, websites for learning resources of this industry?

243. What are expectations from this new role which we are giving you and what we can expect from your side as well?

244. Why did you choose this career or degree path or training that you did?

245. How do you choose what companies and roles to apply for?

246. If you get this job then what do you want to achieve in the next first week, month or year?

247. According to you, how will your family, friends and others describe you?

248. Where do you believe our industry or company will reach in the next 5 or 10 years?

249. Tell us one thing that you would be happy to do for the rest of your career every single day?

250. If you get offered more than one job then how will you decide to choose or accept which one?

251. What role do you want in our company? A manager, leader or executive?

252. After getting out of bed, what kind of work makes you excited to get up on Monday morning?

253. How would you delegate tasks to your team and manage them?

254. What kind of work environment do you prefer the most?

255. Can you tell me about a time when you overcame any challenges and now you can perform it well?

256. What prompts you to get up early and come to work on your last day of job?

257. What are the personal and professional accomplishments that you are most proud of?

258. How would you pitch a product or service to an unknown person whom you met on the street?

259. If a client or senior would ask you for something outside of the scope of your job description, training or otherwise how would you handle it?

260. If you had multiple projects and limited time, how would you go about managing your priorities?

Interesting questions to ask your crush

Want to conversate with your crush? No, no that wouldn’t be romantic. But these questions help you to spend more time with your crush by asking fun and interesting questions.

261. When you’re unhappy or lonely, where do you go the most to relieve the sadness and be happy?

262. Who are you closest to, between your father and mother? And why?

263. Is there somebody in your family who you look up to?

264. Do you feel that your family isn’t supporting you enough and why are they doing this?

265. Which of your siblings do you have a close relationship with and you have special bonding?

266. How many women/men have turned down your marriage proposal? Do you feel bad about this?

267. Which is better: McDonald’s or Kentucky Fried Chicken?

268. What happened in your sex life that altered everything?

269. What would you like to forget, but it has stayed with you even if you don’t want to?

270. Did you ever gaze at a woman or a man in the supermarket when you went shopping?

271. Have you ever considered committing death by committee? If so, what was the motivating factor?

272. What are the things you must accomplish on a daily basis at all costs?

273. What thoughts do you prefer to avoid but find nearly hard to do so?

274. Which of your dream jobs are you willing to give up everything for and why?

275. When do you believe you’ll be qualified for your desired job and how much time it will take?

276. When do you think you’ll have accomplished most of your goals and consider yourself as a successful man or woman?

277. Consider the following scenario. Your family is pressuring you to marry someone you don’t like, or they are having an affair with you. What are your plans?

278. Is it possible to marry someone you don’t like simply to appease your family?

279. What would you do if you discovered that your parents are not your biological parents? What would you do in this situation?

280. What if you go out with your crush and he or she falls in love with someone else?

281. Do you care deeply about your boyfriend/girlfriend and why do that?

282. Can you only eat one food for the rest of your life?

283. Have you ever been in love with more than one person at the same time? Is that possible?

284. What did you buy from your first paycheck from a new job? And for whom?

285. What can be the gift that you will buy for your wife when she gives birth to the first child?

Interesting icebreaker questions

In the environment of a busy schedule, boring meetings, small talk and awkward silences, icebreaker questions are what can benefit it. These are some of the relaxed, fun and simple conversations that will encourage the employees to give genuine answers. 

286. Would you like to live where there is only snow or the temperature never falls below 100 degrees?

287. Would you like to run at 100 miles per hour or fly at 10 miles per hour?

288. Apart from graduating, what is your number one goal for your remaining time in college?

289. What was the most surprising event for you, when you first arrived at the campus or when you first started the classes?

290. If I ever visit your hometown, then what locations would you suggest I visit?

291. If you can choose any name other than your name then what would you choose?

292. If you get a chance to switch life with one person then whom would you like to switch?

293. Can you describe a time when you laughed so hard that you thought you could cry or when you did cry? What was so funny that time?

294. What is the one thing that you want old generations to convey about teenagers today?

295. Suppose if you are independently wealthy and don’t have to work then what would you do with your time?

296. If we told you to delete 2 apps from your mobile then which you will delete and why?

297. What is your favorite Disney hero or heroine? Would you like to trade places with them?

298. If you are going to sail around the work then what will be the name of your boat?

299. Which decade do you love the most among 60s, 70s, 80s and 90s? And why do you still love it?

300. If you get left on a deserted land with no one or either your enemy then which would you choose and why?

301. If aliens landed on the earth any day and offered to take you home with them then would you go?

302. If you were a wrestler then what would be your entrance theme song?

303. If you had your own late night show then who do you want to invite as the first guest?

304. A movie is made on your life then what genre would it be and who would play you?

305. What is your most useful tip to handle distractions while working from home?

306. How many cups of tea, coffee or beverage of choice if you have every morning and why?

307. If you could write a book then what genre would you write in it? Mystery, thriller, romance, historical fiction characters, or nonfiction?

308. Do you like to work from home? Would you rather prefer the office environment? Or is there a balance of both that you like the most?

309. What’s the hardest and easiest part of working virtually for you?

310. Which area of your home do you prefer most for working from home? Backyard, bed, your kitchen table, dining table or sofa?

Interesting get to know you questions

If you want to know someone better then these interesting questions will help you to understand someone’s life choices and opinions in a better way. Let’s have a look at them.

311. Is there any movie that you can practically quote from start to end?

312. What was the thing that you did last time and regret doing till now?

313. The house is on fire and everyone gets out safely, even pets and all cash and money are saved. If 314. you can get a chance to get something that what it would be?

315. What is that one thing that you enjoyed doing but hated by everyone else?

316. Who is the most impressive popular person alive today and why?

317. Do you think that psychic abilities exist? Then which one would you like to have?

318. Do you think that people should post everything on social media as they are doing these days?

319. What would you choose, giving up social media or eating the same meal for the rest of your life?

320. Do you have any major goals in life that you are really ambitious towards?

321. What’s the most spontaneous thing that you have ever done so far?

322. In 40 years, what do you think will be most nostalgic about?

323. If we give a one to describe your family then what would it be and how do you want to describe it?

324. Which 3 famous people whether living or dead, would you want at your fantasy dinner party?

325. If you could shop for free fr one famous store then which one would you choose?

326. If I were a time traveller then would you travel back in time with me without going back to the present?

327. If there is only the last sandwich left on the planet then will you give it to me or your dog?

328. If you could dedicate your life to solving a problem then what problem would you like to sort out?

329. Which is one of your bigger fears that you are willing to overcome?

330. According to you, what’s the nicest thing that I have given you and you were not expecting this from me?

331. What can be the complete worst name that you could give your child?

332. Can you give a common reason that makes your siblings fight with you usually?

333. What are things that are posted on your social media accounts that you regret and delete later?

334. How important is the sense of humour for you when you choose your life partner?

335. If you get an opportunity to meet your favourite author then will you allow him to write the story of your life?

336. Have you ever loved what you were working on so hard that you lost track of them?

337. Do you think strong relationships are easy to manage in a workplace?

338. What was the worst thing that happened to your personal life that affected your focus on working life?

339. According to you, what’s the superpower that you think can save the earth from being destroyed?

Interesting never have I ever questions

The trendy “Never Have I Ever” questions are most interesting to ask in a group conversation. You can play this as a game to let everybody tell you what they have never ever done in their life. Take a look at these questions.

340. Never have I ever had a bank account overdraft.

341. Never have I ever eaten another person’s lunch from the office refrigerator.

342. Never have I ever read a partner’s text messages before.

343. Never have I ever read an email from a partner before.

344. Never have I ever been admitted to the hospital for anything other than giving birth or being born.

345. Never have I ever attempted to learn a foreign language.

346. Never have I ever sent a stranger a drink before.

347. Never have I ever accepted a drink from a stranger before.

348. Never have I ever lied about my earnings.

349. Never have I ever been busy in a public area before.

350. Never have I ever been nude in public before.

351. Never have I ever dated or hooked up with someone ten years my senior.

352. Never have I ever campaigned for a political candidate in my entire life.

353. Never have I ever smoked something which I swear to keep as a secret.

354. Never have I ever destroyed someone else’s holiday and secrecy.

355. Never have I ever been awake for 25 continuous hours or more.

356. Never have I ever accidentally said “I love you” to someone.

357. Never have I ever flirted and cried my way out of a ticket.

358. Never have I snooped through a cabinet, friend’s room or property.

359. Never have I ever worked with someone I can’t stand.

360. Never have I ever dated or hooked up with someone who is of the same gender.

361. Never have I ever thrown someone else a surprise party or dinner.

362. Never have I ever seen something creepy while using public transportation.

Interesting questions to ask on a date

Ahh, first date! Nothing can beat a first date joy and nervousness. To make your first date memorable and enjoyable you have to ask exciting questions. Here are some of the Interesting questions to ask with your partner on a date.

363. Are you a morning person or a night owl?

364. Are you working on any particular passion projects that you are passionate about?

365. What type of pet have you had since childhood and why is it so?

366. What are your etiquettes and how long have you been following them?

367. What was your memorable and favourite family vacation when you were a kid?

368. If you like an artist, then what’s your favorite piece of art?

369. What’s the idea of dating that you hate the most?

370. Do you prefer indoors or the outdoors or do you like them both equally?

371. What’s the special thing that you know and people are always excited to learn from you?

372. In a new relationship, what is the one thing that you are dying to try?

373. For what do you usually feel shy and secure? And why do you do that?

374. What made you fall in love with one of your favourite musicians the first time?

375. Do you have any siblings? If yes, then how much do you have?

376. Have you ever wanted to remove someone from your life who is not right?

377. What’s the favourite TV series you find yourself combing back and re-watching?

378. Do you have any best friends then how did you meet him or her?

379. What are your thoughts on the political situation of our country and people?

380. Do you have male friends and if yes then what do you find most common among them that interest you?

381. Do you have any tattoos? If so, then why do you have that and what’s the meaning behind that?

382. What were your funniest and dumb injury that you have ever suffered?

383. How much do you want you could easily set yourself on fire each day?

384. What you can call a peanut butter if it had a different name?

385. What’s the most ridiculous thing that you have done in the name of life till now?

386. Tell me the most embarrassing thing that you have ever looked at google?

387. What would you do if you are on a plane that’s going down and there is only one parachute for you and your husband or wife or girlfriend/boyfriend?

388. How many donuts can you put in your mouth at once?

389. Have you ever been in a situation where you needed to make others laugh and have fun?

390. Will you maintain your body and mind of a 20 year old self if you lived to 100 years?

391. How much longer will you go to sit in pain rather than get up early and get a remote which is out of reach?

392. How much longer will it take you to finish the first round of popcorn during the first movie theatre preview?

393. What abilities do you have that will help you in surviving a zombie apocalypse?

Interesting questions to ask your partner

Spending a whole life with someone needs better future planning and understanding. Therefore, these exciting and deep thought questions can help you to make the long term relationship stronger and better day by day. Take a look at personal questions to ask a guy or girl.

394. Do you want children? If so, how much do you want?

395. Do you like pets? Are you a cat person or a dog person or are those things deal breakers?

396. If you want to get married soon, do you want the ceremony to be large or small?

397. Do you want to compromise with something? If so, then what are you not willing to compromise on?

398. Are you satisfied with our intimate life? What improvements do you want in this?

399. Can we make each better person and lift up each other in personal and professional life?

400. Do you want to get married with few plans? What are your plans to move together? 

401. What’s something you would do before marriage? Do you want to move after engagement or marriage and where?

402. Are you ready to commit to a long term relationship?

403. What’s the most favourite thing that you like about me and are you ready to talk about life companionship?

404. Do you believe in religion and what are your thoughts on religion in case of conversion?

405. What makes you feel the most loved? Chocolate, go on a walk, little notes and cute good morning text?

406. What is your most favourite romantic fantasy?

407. According to you, what’s the best setting for date night?

408. What’s your memorable and best vacation you have ever taken?

409. What is the most important childhood memory that you still remember and fill with love when you enjoy?

410. Do you enjoy cooking? Will you enjoy it if we cook together and eat after that?

411. If money doesn’t matter for you then what would you want to do for a living?

412. What’s your greatest talent and biggest weakness in your life and how do you handle them with grace?

413. What’s your weirdest habit or quirk before it comes up will save you the surprise of discovering on your own?

Funny interesting questions

Having fun in a conversation is essential to have. Make your boring conversation fun and exciting with these fun questions and ideas to ask your friends, family members or colleagues. These are some funny questions to ask a girl as well.

414. What would you do if you were granted a one-minute commercial time during the Super Bowl that you couldn’t sell?

415. What is the most ludicrous thing you’ve been duped into doing or believing?

416. What have you read or seen this week that has piqued your interest?

417. What would you ask if you could know the absolute and whole truth to one question?

418. What is something your brain attempts to persuade you to do but you have to fight it?

419. What problem or condition did TV/movies lead you to believe was typical, but it wasn’t when you grew up?

420. Do you fold your toilet paper when you wipe?

421. When was the last time you screwed something up and no one noticed?

422. What is the most bizarre thing one of your professors has ever done?

423. What’s the most offensive commercial you’ve seen recently? What’s the deal with it being so bad?

424. What’s your kitchen’s biggest blunder?

425. What are some examples of praises that actually insult?

426. What would you call yourself if you had to change your name, and why would you choose that name?

427. What are your favourite and least favourite purchases?

428. Which fictional figure would be the most inconvenient to meet in person?

429. What is the most inexcusable way you’ve been hurt?

430. What portion of your body would you be willing to give up?

431. Which celebrity do you think deserves a perfect ten?

432. What is the most foul-smelling place you’ve ever visited?

433. What would be on your life’s joke reel?

434. What is the most worthless skill you possess?

435. If you had a boat, what would you name it?

436. What comes closest to genuine magic?

437. Do you know who is the messiest person you know?

438. What will be the ultimate straw for the internet?

Interesting conversation questions

For any conversation, you not only need facts and concepts but some thought provoking kind of questions can also make your group communication enlightening and engaging. 

439. What are you willing to experience the most in the next 5 years and why?

440. Do you remember the last time when you helped someone and what you did to help them?

441. According to you, what’s the meaning and measure of success and failure in life?

442. Apart from loved ones, which item would you like to save on a house fire?

443. Which is the one thing that you want people to talk about less and what’s the one thing that you want to speak more about?

444. Would you like to be famous with a viral video? If yes then for what and why?

445. Do you ever rehearse the important tails or conduct a conversation with yourself as well?

446. Which one project do you want to understand from so many times? And why haven’t you got it yet?

447. Can you tell me a silly and made up game that you usually play as a child?

448. Where in the world do you want to teleport right now? And what would you be doing there?

449. Describe one thing that your younger self will not believe about your life these days?

450. Who was your favourite teacher in school and why would you like them?

451. If you get a chance to go in another time period then what era would you like to choose?

452. Do you like pet names? If so, then what would you like to choose for yourself?

453. If you ask a question to your pet and have them answer then what would it be?

454. Has any book that you read so far impacted your life and brought change in a positive response?

455. Which city in the world would you like to choose for living for the rest of your life and why?

456. What does your dream home look like? Can you describe it to me?

457. What is your most favourite and worst thing about the internet nowadays?

458. Tell me one thing that you think people should not do anymore?

459. What’s the one life story of yours that you are excited to tell your children one day?

460. Which TV or cartoon fictional character can you resemble with your roommates?

461. Which song you are playing to repeat for so many years and why do you like it?

462. Describe your favourite part of your personality that you love the most?

463. Which one quality that you want in all your friends, family members and loved ones?

Interesting questions about life

If you are someone who loves to talk about life, and real situations that you observe often and rarely. So, here are some of the interesting questions based on life that you can ask. 

464. Is it true that life gives me everything I desire?

465. Should we not say anything in a personal or general circumstance, even if we strongly disagree, if being quiet makes things easier?

466. What’s the one thing you’d leave behind if we all vanished tomorrow?

467. What if there was no such thing as linear time? How can we continually be moving forward?

468. Is my “being” meditation more powerful than the animals? Is there such a thing as solipsism in nonhuman animals?

469. Why do I keep acting as if I’m the centre of the universe?

470. What exactly is the purpose of life? Why do we continue to live as if there is no end when the next moment could be the final chapter?

471. What happens once I leave?

472. Who should we include in our family?

473. Is it possible to strike a balance between the conventional and the unconventional? Is your traditional side a societal reaction or the true you? Do your outlandish characteristics define you, or can they be attributable to peer pressure?

474. Are people having an impact on me and influencing my decisions?

475. How do you select between immediate enjoyment and a longer-term goal?

476. How can you tell what is useful and what isn’t unless you try?

477. Is it true that I’m learning something new every day?

478. Do a lot of people problems evolve or do we continue to think about the same things?

479. We now prioritise ourselves over everyone else. But what if we were forced to do it in the opposite 480. direction? Is it possible that the system will work?

481. Is it true that working less is such a wonderful thing as everyone claims?

482. What if money didn’t lead to prestige but instead served a more basic purpose?

483. Are we, as humans, becoming more accepting or more strict in general?

484. Would I still be doing what I’m doing today if money didn’t exist?

485. What motivates me to get through each day? What is the source of my motivation?

486. Should we act as though we know something even if we don’t?

487. Why do people always believe that everything is fine?

489. Everything is fine until I start comparing my life to the lives of others. Why do I stop being appreciative for what I have virtually every other second, despite knowing this?

490. Are we all giving it our all right now?

Interesting questions for couples

A romantic and intimate relationship does not always mean touches and gestures. But sometimes quite interesting questions about your life make the relationship even more romantic and pleasurable. 

491. Tell me one of the places in the world where you always wanted to travel?

492. What are the highest valued things in your life and bucket list?

493. Do you want to move somewhere else or just want to stay where you are today?

494. If you can gain one quality and ability within yourself then what would it be?

495. How can you resolve and foresee the most persistent problems in our life?

496. Do you have any goals for this relationship? If so then what are those?

497. Is there anything in your life which you are hesitating to complete and I can help you to accomplish that?

498. When did you first realise that you should be in a relationship with me?

499. What are the things you provide more value from the beginning of our relationship?

500. What are situations in which you feel most safe and secure in our relationship?

501. What’s your favourite food that you want to share on date night?

502. What are the physical and emotional gestures that you prefer the most?

503. What are the experiences and circumstances in your life that inspired your philosophy of love?

504. What is the one thing that can make your relationship long lasting?

505. What’s the perfect day that looks like to you?

506. Are there any people from your family or friends to whom you want to get closer and why?

507. Was there any conflict between us in the past that you think isn’t solved yet?

508. Which one of the family members you loved the most when you were young?

509. According to you, what does a balanced relationship look like?

510. What is the ultimate idea of having a healthy and beautiful relationship?

511. Is there anything about me and my life that you wanted to know but you don’t know right now?

512. What is the extent of your religious ideology, if any?

513. What are some things in your life that you are most grateful for? Is that me too?

514. What’s the last time you visited your hometown and how much did you enjoy it there?

515. Do you want to visit the most romantic place in the world with me?

Interesting sex questions

Is your sex life is getting boring? Then ask these questions to your partner in order to make your intimate relationship more romantic and stronger. For a better sex life, being genuine and open with your partner regarding every aspect is the key to have more fun. 

516. What is your most horrible sexual fantasy?

517. How many persons have you had sexual relations with?

518. What’s the strangest place you’ve ever had sex?

519. Which portion of my body is your favourite?

520. What would you wear if you had the option to choose what I was wearing right now?

521. What part of your body do you prefer to be touched?

522. When was the last time you experienced a dream that was filthy?

523. Where would you have sex if you could have it anyplace in the world?

524. Have you ever had an affair with a coworker?

525. What would you do if I said I wanted to have sex right now when we were out to dinner?

526. Who would you sleep with if you could sleep with any celebrity?

527. Would you or have you participated in group sex?

528. What is the most sex you’ve ever had in a single day?

529. Do you prefer to be loud or silent during sex?

530. Have you ever used food as a foreplay tool?

531. Have you ever attempted to make a sex tape?

532. What is the first thing that draws you to someone sexually?

533. How far have you gone/would you go in terms of BDSM?

534. Which toy is your personal favourite?

535. Have you become a member of the mile high club?

536. Do you believe you could remove my panties without using your hands?

537. Do you like having sex in the shower?

538. Where have you ever masturbated in the strangest location?

539. What was the most humiliating sexual experience you’ve ever had?

540. Have you ever had sexual fantasies about someone else?

Interesting truth or dare questions

Have you ever played a truth and dare game? Then you surely know how much fun it is. For making this game more fun you can ask these questions to your group members and have a pleasurable game at the end.

541. What would you do first if you had the ability to become invisible?

542. What’s a family secret you’ve kept hidden from your parents?

543. What is the most humiliating music you have ever heard?

544. What is one aspect of yourself that you wish you could change?

545. On social media, who was the famous person you stalked?

546. What three wishes would you make if you had three wishes granted by a genie?

547. What’s the strangest place you’ve ever used the restroom?

548. What is the largest amount of food you’ve ever consumed in one sitting?

549. Which player would be the first to die if there was a zombie apocalypse?

550. What reason have you previously used to avoid making arrangements with a friend?

551. Read aloud the last message you sent to your best friend or significant other.

552. What is the greatest period of time that you have gone without showering?

553. What is your phone’s most embarrassing most-played song?

554. Who would you prefer to be if you could be a fictional character for a day?

555. What song would you choose if you could only listen to one for the rest of your life?

556. What is a deal breaker when it comes to a potential love interest?

557. What would you eat if you could only eat one thing for the rest of your life?

558. Give your phone to another player, who will be able to send a single text message to everyone they wish.

559. Make a fool of yourself by imitating another player until you can figure out who it is.

560. Until it’s your turn again, say pickles at the end of every phrase you say.

561. Imitate a YouTube celebrity until another player figures out who you are.

562. Allow someone else to use a permanent marker to draw a tattoo on your back.

563. Put on a blindfold and touch the faces of the other players until you figure out who they are.

564. Dump out what’s in your handbag, backpack, or pockets and do a show-and-tell.

565. Allow another player to make a hat out of toilet paper, which you must wear for the remainder of the game.

Random interesting questions

Why do you need to think a lot about what to say and what not to say in a conversation? When you can have the most creative list in your random mind.

If you want to get out of the boring conversation and indulge in excellent conversation then have a look at these random questions to ask a girl, guy or anyone. 

566. What is the one good that you haven’t eaten yet but you want to try as soon as possible?

567. What are some of the red flags that we should watch out for in our daily life?

568. When you will be old, what do you think that children will ask you to tell the stories about?

569. If you can switch two movie characters then what switch will lead you to the most appropriate movie?

570. How much can a country change if everyone no matter their age can vote?

571. If your job gives you a three day surprise paid break to rest and enjoy then what would you do in those three days?

572. What’s the most bizarre way that you have seen someone getting fired or quit?

573. What’s the thing that remains always trendy and in fashion no matter how much time passes?

574. Which actor or actress plays the same character in almost every movie or any show they do?

575. In ancient times, people were buried with the essential items to use in their afterlife. What would you want to bury with you so that you can use it in the afterlife?

576. What’s the best or worst real joke that you have played on someone or that was played on you?

577. Which ice cream flavour do you like the most?

578. What is the spiciest and sweetest thing that you have ever eaten in your life?

579. What obstacles can be induced in the world’s most amazing obstacle course?

580. What’s the unethical thing that would have the biggest positive impact on society as a whole? 

581. When was the last time when we’re snooping and found something that you have never expected?

582. What’s the smartphone feature that you are really willing to incorporate by the mobile companies?

583. Do you think that children born these days would have a worse or better life than their parents?

584. What is your favourite movie quote that you usually use in your daily life?

585. Which TV character do you want to change places with for a week or so for fun?

586. If you were a ghost and could control people, what would you make them do?

587. According to you, what’s the one goal that humanity is not focusing on achieving right now?

588. Tell me the most comfortable chair or bed that you have ever sorted on?

589. Which music band or artist do you always advise when someone asks you for a music recommendation?

590. Have you ever eaten food that’s past its expiration date if it smells or looks good?

591. Which protagonist of a book or a movie would make the worst roommate?

Interesting psychology questions

Psychological questions of all time ranked from worst to best don’t always appreciate the pure fun of getting to know your partner better or finding out if someone is crazy.

We all know that psychological deep questions are important to getting to know yourself better and your loved ones as well. 

592. What irritates you the most?

593. What would you like to be remembered for?

594. How do you get rid of your bad habits?

595. Do you think there is an afterlife?

596. What do you consider to be your greatest achievement?

597. What do you mean when you say you love someone?

598. How would you describe your “Perfect” day?

599. What is the meaning of death?

600. Do you want to be well-known?

601. What is the key to dealing with life’s issues?

602. What does it mean to have a sense of community?

603. What is self-actualization and what does it mean?

604. Do you think nature or nurture is more important?

605. What would you steal in what situation?

606. Would you assist someone in need?

607. If you could invite anyone to dinner, who would you invite?

608. Would you follow an order to inflict harm on someone?

609. Would you make a good eyewitness if a crime was committed against you?

610. What are some of your favorite activities?

611. Who do you consider to be the most important person in your life?

612. What personality trait do you have the most of?

613. Do you have a happy or sad mood when you wake up?

614. Do you identify as an introvert or an extrovert?

615. What brings a smile to your face?

Interesting questions to ask your mum

Have you ever sat with your mum and had a long, great conversation? If you are willing to do so then try these questions and understand your mum’s thoughts and what they want in their life. Here are some of the questions you can ask your mum. 

616. Before meeting my father, how many boyfriends did you have?

617. Do you truly love me, or are you simply saying it for the sake of saying it?

618. Why do you insist on swearing, yet you don’t want me to?

619. Which country do you like to visit when you want to shop for the best wardrobe?

620. When do you believe the best time is for me to get married?

621. Would you still back me up if I decided to be a gay?

622. What did you do as a teen that you don’t want me to do?

623. What is the one thing you regret the most and don’t want me to go through?

624. What was the name of the friend who first exposed you to the world of illegal drugs?

625. How long did you breastfeed me before you started introducing food to me?

626. Did you experience low self-esteem as a result of your pregnancy weight?

627. Do you have any regrets about marrying my father?

628. Have you ever had any strange moments on campus?

629. What obstacles did you have to overcome in order to become the person you are today?

630. Tell me how many times you’ve had your heart shattered before meeting Dad.

631. Tell me about the biggest secret you don’t want your father to know about you.

632. When you were a teen, what was your favourite haircut?

633. When you gave birth to me, how old were you?

Interesting questions to ask your dad

Asking questions to your dad can be a little bit scary but you can ask them even more if you want to know your father’s opinion and what he wants for you. Here are some of the interesting great questions you ask your dad in order to begin conversation.

634. What ideas have you ever abandoned?

635. Since the day you met, how would you define your relationship with your mother?

636. Who approached who between you and your mother?

637. How long had you been dating Mum before she proposed?

638. What was the most important life lesson you learned as a result of this event?

639. Have you ever bribed a cop for a traffic infraction?

640. Are you still pursuing your goals or are you already living them?

641. What do you believe to be your greatest life failure?

642. When you first met Mum, what was it that drew your attention?

643. Who would you vote for: George W. Bush, Barack Obama, or Donald Trump?

644. Which year was the most trying in your life?

645. Have you ever doubted whether or not I am your child?

646. Do you believe that self-assurance is essential for success?

647. Have you ever cheated on a previous partner before meeting your mother? What about mother?

648. When you experience a bad dream, what is the first thing that comes to mind?

649. Do you believe that being a businessman, rather than relying on conventional employment, is the only way to become a millionaire?

650. Do you have any bad habits that go against your core values?

651. What characteristics do you want me to look for in a future wife or husband?

652. Do you see anything odd in our generation’s demeanour?

653. Have you ever taken us to see a movie at a theatre?

654. What aspects of my dress code do you like and dislike?

655. Do you believe that smoking shisha is more dangerous than smoking marijuana?

656. Who do you love the most? Your grandma or grandpa?

657. In 40 years, what do you think you will be most nostalgic for?

Bottom line

Starting and continuing an exciting conversation is not as easy as it seems. In order to engage the people around you or whom you are talking with, you should ask some amazing interesting questions based on their interest.

Not only for engaging conversation but these questions also help to understand one’s mind, behaviour, thoughts and ideas. Whether it’s your life partner, mother, father, stranger or even friends, these questions make the bond more strong and special and eventually fun.

Always remember, nothing can beat a fruitful conversation than hanging out.