300 Examples of Interesting Questions in a Conversation


Every day we walk down the street, and we see new faces, or we’re on the phone, and we see people who are so socially participatory, and it just feels like they’re unreachable people. Being able to make interesting questions and keep the conversation going is a great social skill. So, grab a coffee and go through all of the examples of questions you can ask in any given conversation.

300 Examples of Interesting Questions for ANY type of Conversation

With this article, we expect to make a huge collection of 300 questions for almost any type of conversation or engagement we may have with other people. It’s a work in progress, so not all questions are there yet, which you can quickly skim through here, or click on this Link to download the file.

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Interesting Questions to ask on a Date

Interesting Questions to ask on a Date
1. What are you more grateful for in life?
2. If you could change anything in the way you were created, what would it be?
3. In four minutes, tell me your life story in as much detail as possible.
4. How close and warm is your family? Why?
5. If we became close friends, what should I know about you?
6. For you, is there something we shouldn’t joke/joke about? What? Why?

When you go on a date with someone you just met or didn’t have much intimacy you have to ask crucial questions that allow you to get to know them better without sounding like an interrogation. 

Avoid searching for information about the past and focusing more on knowing what taboos they have, their family, work, and special interests are like.

Questions for Getting acquainted with a stranger

Questions for Getting acquainted with a stranger
7. How do you stay sane after a hard day?
8. What’s your take on polyamory?
9. If you found a cult, what would it be about?
10. How do you prefer to spend your money: objects or experiences?
11. What is the thing your parents can’t even know about you?
12. For you, how would it be the perfect day? Why?

What creates a genuine relationship is not the time we know a person but the connection we create; to make a stranger into someone we know, we need to ask intimate questions and raise reflection to share insights.

Truth or Dare Question Examples

Truth or Dare Question Examples
13. A person will throw something in the toilet, and then you have to take it back with your bare hands.
14. Try juggling three objects the group chooses.
15. Try drinking a glass of water (or beer, if you have) using your feet.
16. Post an embarrassing photo on your Instagram or Facebook
17. Drink five shots of tequila for each truth passed.

Playing truth or consequences with people we’ve just met can be a bit uncomfortable; we ask about being right or untrue, someone we know the least, and challenges to whom we know the limits.

The goal of the truth or dare game is to create a fun scenario that everyone can participate in.

Questions to ask When meeting someone we admire

Questions to ask When meeting someone we admire
18. What is your biggest inspiration?
19. How did you pushed yourself to accomplish the life you live today?
20. What separates the dream from what we can achieve in reality?
21. How do you manage to come true to your goals?
22. Tell me about some books or people that inspire you and why

The opportunity to meet someone you admire should be used to acquire knowledge and grow. So questions in the table above are looking at how intelligently they’ve become in the people we admire today.

Questions to ask In a biographical interview 

Questions to ask In a biographical interview 
23. What kind of trials and tragedies did your family have while you were growing up?
24. Are there any unusual genetic traits in your family lineage?
25. Name two or three dishes that your mother or father made that were especially memorable?
26. What are some of the personal values that are very important to you? What have you done (and are you doing now) to teach these values to your children?
27. List at least five people you would classify as truly great men and women. What did they do to be great?
28. How do you describe your personality?

A biographical interview is one in which we ask personal questions without fear to get to know a little more intimate people generally known by some socially recognized feat.

When talking about the meaning of life

Questions to ask When talking about the meaning of life

29. Are you holding onto something you should let go of?
30. Do you live your life to be happy or to make others happy?
31. Are you dedicated to something you feel passionate about?
32. What is your purpose in life?
33. What motivates you? Where do you invest your energies?
34. A lesson that you learned during a much unexpected moment.

When talking to someone about the meaning of life, we want to ask reflective questions that make them look at themselves, expose existential crises, help solve directional problems, and more.

To talk about life’s meaning, we do not need to be close to someone; however, it requires us to be observant people to know the right time to address these questions.

Questions to ask When talking about our job or someone else’s 

Questions to ask When talking about our job or someone else’s 
35. What made you choose this job?

36. Interesting Questions to ask when talking about our or someone else’s
37. If money were not a necessity, would you continue with the same job? Why?
38. What cool conferences have you attended and why?
39.
40.
41.

By asking questions about other people’s work, we make them think about the decisions that got them there and make us know a little bit more about different professions.

Questions to ask when getting to know a particular religion

Questions to ask when getting to know a particular religion
42. What are your cultural habits?

43. Interesting Questions to ask when getting to know a particular religion
44. Does the perspective of life make sense to me?
45. Do you think that being religious and spiritual is different? How come?
46.  What would your life look like joining this religion?
47.
48.

When we ask questions about different religions, we know if we are the type of person interested in the religious life and, if so, to what extent it is essential for the person we are meeting or for us.

Interesting Questions When asking someone about themselves

Interesting Questions When asking someone about themselves
49. What would you like to know about me?

50. Interesting Questions to ask when asking  someone about themselves
51. When did you see me? What was your first impression?
52. Tell me something vital about you.
53. What are your hobbies?
54. Tell me about your dream travel.
55. Tell me about something that interests you, but not many people enjoy it.

When we ask someone about you in an interesting way, we seek to know crucial questions about your personality, hobbies, and how you deal with difficult times, so we don’t get scared later.

Interesting Questions To ask in a Job interview

Interesting Questions To ask in a Job interview
56. Tell me about a situation you had to work under pressure.

57. Interesting Questions to ask in a job interview
58. Why should we hire you?
59. Tell me about a conflict you’ve had at work and how you handled it.
60. What do you think the company can do differently?
61. How do you assess your abilities with emotional intelligence?
62. Tell us about a situation where you had a great challenge and how you solved it.

When we ask open questions to the interviewee, we allow him to talk more about his professional experience, to know if there is other knowledge outside of those mentioned in the curriculum and personality.

Questions to ask In the waiting line

Questions to ask In the waiting line

63. What is the longest line that you have to be?
64. How many times have you been here?
65. What is the weirdest thing that has happened to you in a waiting line?
66. What is your astrological sign?
67. How long can you go without checking your phone?
68. If you could have tea with a fictional character, who would that be?

Instead of being in a bored room, we can make a waiting line a way of breaking the ice with someone we just met or have been trying to interact with. We can use the waiting line.

Questions to ask the cashier in a café

Questions to ask the cashier in a café

69. What do you think I should order?
70. If you could only have one drink, which one would it be?
71. If you had $50, how would you spend it?
72. What is something you wish you could do every day?
73. What is your guilty pleasure?
74.

We can meet interesting people anywhere. In a cafe, it would not be different. The table above questions can make us know a little more than the worker of our favorite place maybe sit down and develop a more personal conversation around.

Questions to ask the locals in a new city

Questions to ask the locals in a new city
75. What is the calmest place to hang out?
76. If you could only live in any place in the World and never come back, which place would it be?
77. Would you switch roles with your parents if you had a chance? How do you think it would be?
78. How do you make friends?
79. What is your favorite place?
80. How are the people and the culture here?

Interacting with locals in a new city allows us to ask more intimate questions to get to know the city from a more inside perspective. We will be much earlier to live some of the cultures and visit interesting places when we see it.

Interesting Questions to ask At a slumber party

Interesting Questions to ask At a slumber party
81. What is the scariest experience you’ve lived?
82. Do you believe in ghosts and spirits?
83. Would you rather have an infinite dream or infinite insomnia?
84. What is the worst date you ever been on?
85. What is your favorite celebrity scandal?
86. Do you have or had an imaginary friend? What’s her/his name?

A slumber party is an opportunity to discover the things that our friends feel comfortable and uncomfortable doing and find out a bit about the past and plans.

Interesting Questions to ask At a networking event

Interesting Questions to ask At a networking event
87. How was it starting your own business?
88. Back there, did you feel scared about the decisions you were taking? Why?
89. What is the first thing you do when you wake up in the morning?
90. What is your dream job?
91. What talent did you wish you had?
92. What is your favorite weekend activity?

A networking event serves to meet new people and make new contacts in personal and professional life; thus, here is not the time to feel timid because many of the people who go here seek the same.

Interesting Questions to ask At a gallery tour

Interesting Questions to ask At a gallery tour
93. What kind of art do you care about more? Why?
94. How do you feel when you see a specific type of art?
95. Have you ever been to Google Art tours?
96. How would you describe your taste in art?
97. How did you hear about this event?
98. Describe the most captivating painting or artwork you’ve ever seen.

In a gallery art, we meet many people with objectives in typical art, so talking about it would not be inappropriate.

Questions to ask During classes

Questions to ask During classes
99. How do you see yourself in 5 years?
100. What is the biggest challenge about studying?
101. Do you have strengths that help you succeed? Which ones?
102. What is your biggest goal in life?
103.
104.

Classes are one of the most interacting moments with divergent social groups, so we have the opportunity to make new friends by helping them think a little bit about the choices that brought them there and how that would be part of their future life.

Questions to ask While video calling a friend that lives abroad 

Questions to ask While video calling a friend that lives abroad 
105. What’s the lifestyle like in this country?
106. If you could take me to see a place where you are now where it would be and why?
107. How it’s like living abroad?
108. Draw a line between your home country and where you are living now.
109. Let’s have a virtual cooking date.
110. Do you see yourself living there for the next three years?

Chatting and virtual meetings with friends living abroad are great opportunities to look at what kind of future we see ourselves and know about the things that have made our friends happy.

Questions to ask When camping 

Questions to ask When camping 
111. What are you most passionate about?
112. Are you a cat person or a dog person?
113. When you die, what do you want to be reincarnated as?
114. Where is the most exotic place you ever been to?
115. Oceans or Mountains? Why?
116. Is there a place in the World that you feel represents who you are? Where and why?

Camping is a great way to look at the lifestyle we lead and how we want it to stay or change, so an excellent opportunity to discover adventures that our friends have done or would like to do.

Questions to ask while watching a fashion show

Questions to ask while watching a fashion show
117. What do you think is the designer’s inspiration?
118. What did you think about the last France Fashion Week collections?
119. Do you prefer customized clothes, or does it not matter?
120.
121.
122.

A fashion show is a great place to make contacts and friends, and we do not need to be afraid to talk or ask for fashion tips after all the people who have something in common already.

Questions to ask When talking to someone new through social media

Questions to ask When talking to someone new through social media
123. Where do you think motivation comes from?
124. Have you ever hiked Kilimanjaro? Do you want to go?
125. Pineapple Pizza or too wild for you?
126. If you had to describe yourself in 4 words, what would they be?
127. What is the one place you’d love to travel to again? Why?
128. Where do you feel most centered and happy?

When we talk to someone unknown on the Internet, we should try to be the most out of the box possible because they already interact with unfamiliar people several times.

Questions to ask At a reading club

Questions to ask At a reading club
129. Which book made you change your life (habits)
130. What expectations did he have of the book? Did the book comply?
131. How would you describe the plot? Did it attract you, or did you feel you had to force yourself to read the book?
132. Which character did you identify with the most and why?
133. How could the book have been different if it happened at another time or place?
134. At what point in the book did you feel most involved?

A reading club is a great way to reflect on life because they are a flu of people who read books and discuss different approaches to the same book.

Questions to ask while Making a spiritual journey

Questions to ask while Making a spiritual journey
135. How can I find self-knowledge?
136. What is my Spiritual destiny?
137. What is happiness for me? I am doing what it takes?
138. Am I paying attention to which kind of people are making part of my life?
139. What is the point of living?
140. Am I real with myself?

A spiritual journey is a great way to change your life and cycle of friends, if any; there is a film called Eat, Pray and Love that explains and tells the story of a young woman who at one time was married but unhappy and in the other was traveling the World in search of you.

Questions to ask When joining a new group class

Questions to ask When joining a new group class
141. How do you attribute tasks?
142. How do you proceed when a member I having trouble with a task?
143. What is your name?
144. What made you join this class?
145. If you could make up a project, what would it be like?
146. What is your favorite subject, and why?

Questions To ask in a lecture 

Questions To ask in a lecture 
147. Could you explain that further?
148. Could you give us real-life examples of what you mean?
149.
150.
151.
152.

Questions to ask In a quick exchange 

Interesting Questions to ask In a quick exchange 
153. Your nail design is creative. Did you do it?
154. What is your favorite cartoon, and why?
155. The best place to relax would be the beach or shopping?
156. Did you know that when someone is with flu in Japan, they take several cares, including using a mask? What do you think about that?
157. What was the most challenging thing you did as a kid?
158.

Questions to ask On a talk show

Interesting Questions to Ask On a talk show
159. Do you feel comfortable here?
160. What is the best decision you have ever taken for your well-being but everybody told you it was selfish?
161.
162.
163.
164.

Questions to ask On the studio 

Interesting Questions to ask On the studio 
165. When you produce another music with a similar beat to do you use the same sample?
166. Where does the rehearsal take place?
167. Do you have a music/ photographer degree? How was the learning experience?
168. Do you do photoshop? 
169. How much time does it take to edit a photo?
170. How do you choose the final versions?

Questions to ask On a Netflix and chill hangout 

Interesting Questions to Ask On a Netflix and chill hangout 
171. How do you choose your movies?
172. Have you ever played Sims? What do you think about it?
173. What do you wear when you feel you’re very best? Why?
174. What do you love most about your home?
175. What gives you goosebumps?
176.

Questions to Ask On a text message 

Interesting Questions to Ask On a text message 
177. Which movie do you love and why?
178. What music could you listen to for the rest of your life?
179. Tell me something about yourself nobody knows. 
180. Tell me about a memorable experience.
181.
182.

Questions to ask At a videogame store

Interesting Questions to ask At a videogame store
183. Which game got you playing for months and months?
184. Have you ever played a life simulation game?
185. Have you ever visualized your life as a game? Can you explain?
186. Do you prefer battle games or the ones you play by yourself?
187.
188.

Questions to ask upon meeting the Queen of England.

Questions to ask upon meeting the Queen of England.
189. Have you ever visualized how life could be if you were not a royal member?
190. What is one piece of advice you would give to your younger self?
191.
192.
193.
194.

Questions to ask when Meeting your lover‘s family 

Questions to ask when Meeting your lover‘s family
195. What she/he was like growing up?
196. What’s one value that you made sure he/she acquired growing up?
197. What was her biggest talent during childhood?
198. What habit she/he has since childhood?
199. Which death in your family was the one with the most significant impact on her/him? How was their relationship?
200.

Questions to ask when Meeting your boyfriend/ girlfriend‘s friends. 

Questions to ask when Meeting your boyfriend/ girlfriend‘s friends. 
201. Do you think she/he is a friend you can count on?
202. Which kind of things triggers her/him?
203. How would you describe his/her personality?
204.
205.
206.

Questions to ask In a conversation with your coworkers after work 

Questions to ask In a conversation with your coworkers after work 
207. Would you rather be smart or happy?
208. If you could change something about how you were raised, what would it be?
209. Something that you would like to try but never did?
210.
211.
212.

Questions to ask In the train 

Questions to ask In the train 
213. What do you usually think about when you are on the train?
214. What is the one thing that taking the train told you about life?
215.
216.
217.
218.

Questions to ask When your friend tells you about their vacation

Questions to ask When your friend tells you about their vacation
219. What was the best part of the trip?
220. What was the interesting thing that you experienced?
221. Did you meet new people? How?
222. What made you laugh out loud?
223.
224.

Questions to ask When you meet your daughters/ son‘s significant other 

225. How much of what you’re showing me is you and not who you wish me to see?
226. How meaningful is a positive relationship between you and me for your relationship with my daughter/son?
227.
228.
229.
230.

Questions to ask In a family gathering 

Questions to ask In a family gathering 
231. Can you tell a funny story that happened before I was born?
232. Which advice would you give to your grandchild on their marriage day?
233. What was the best thing that happened when you were raising your children?
234. What is the most important thing for you to do as a family?
235.
236.

Questions to ask On holiday

Interesting Questions to ask On holiday
237. What are we grateful for today?
238.
239.
240.
241.
242.

Questions to ask At a memorial

Questions to ask At a memorial
243. Have you ever considered writing a biographical book that could be inherited from father to son and continue to do so?
244.
245.
246.
247.
248.

Questions to ask When shopping at the mall

Questions to ask When shopping at the mall
249. How often am I going to use this?
250.
251.
252.
253.
254.

Questions to ask At a food fair

Questions to ask At a food fair
255. Have you ever taken a tour to unknown restaurants just to taste the food?
256. What is the weirdest and the yummiest food you ever ate?
257. What is your favorite comfort food? Why?
258. What is the best meal you’ve ever had?
259. What is the best meal you’ve ever cooked for yourself?
260. Do you like spicy food?

Questions to ask At a welcome to the neighborhood party

Questions to ask At a welcome to the neighborhood party
261. Why did you move from your other house?
262. How was it like? (Your old neighborhood)
263. What is the best and the worst memory from your old neighborhood?
264. Do you give back or volunteer with any organizations?
265. What is one form of self-expression you’ve been too hesitant to explore?
266. What is your favorite season?

Questions to ask on a Roadtrip

Questions to ask on a Road trip
267. Would you rather drive forever and never get to your destination or stay in one goal forever and never drive around?
268. What are you currently reading? Tell me about it.
269. What food reminds you most of home?
270.
271.
272.

Questions to Ask When Going to Disney for the first time

Questions to Ask When Going to Disney for the first time
273. What is one thing you would add to Disney and one thing you would subtract?
274.
275.
276.
277.
278.

Questions To ask when before being proposed

Questions To ask when before being proposed
279. Why would you like to marry me?
280. What would you consider relationship goals?
281. Do you think we changed since the day we met? Why?
282. Do you feel comfortable with me not telling you everything that may go on?
283. What accomplishments are you most proud of?
284. How do you unwind after work?

Questions to ask When going to the drugstore/ pharmacy 

Questions to ask When going to the drugstore/ pharmacy 
285. Do I need a prescription for what I am going to buy?
286. Where this medicine do comes from, and does it have side effects?
287.
288.
289.
290.

Questions to ask During a Q/A on Instagram live.

Questions to ask During a Q/A on Instagram live.
291. What do you do for a living?
292.
293.
294.
295.
296.

Conclusion

We need to have interesting conversations and the will to get out of the box and dare to ask questions and take actions that we rarely take in everyday life.

Reference and Further Reading

225 Conversations Starters for Any Situation. Gifts

101 Topics to Talk About. Conversations Starters World.

Emidio Amadebai

An avid seeker of knowledge, and passionate about sharing the lessons he picks up in life. Emidio is passionate about public speaking, teaching, and helping others develop critical soft skills, such as communication, leadership, and other interpersonal skills which are in high demand in today's rapidly evolving market.

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