Conversation Starters: 250 Non-Boring Questions for Every Situation
Every conversation has one moment where it either opens up or quietly dies. “So, what do you do?” usually kills it. “What’s something you’ve gotten weirdly good at?” usually opens it.
The 250 conversation starters below are built for that moment. They’re sorted by situation (small talk, friends, dates, work, family dinner, texting and parties) and tagged light, medium or deep, so you can pick a question that fits the room. You’ll also find the 4-step way to start a conversation, rescue lines for when it stalls, topics to talk about, and free printable cards.
There’s a good reason to be a little braver than feels natural. In experiments published in the Journal of Personality and Social Psychology, people expected deeper conversations with strangers to be more awkward than they turned out to be, and underestimated how interested the other person was in their answers (American Psychological Association). A good convo starter is simply permission to skip the boring part.
Quick answer: what makes a good conversation starter?
Good conversation starters are open-ended, specific and easy to answer with a short story instead of a one-word fact. Three of the best: “What’s the best thing that’s happened to you this week?”, “What were you obsessed with at age 12?” and “What’s something you’ve gotten weirdly good at?” Ask one, follow up on the answer, then share your own.
Jump to: Top 10 · How to start a conversation · Small talk · Friends · Fun and funny · 20 random questions · Deep · Dates and couples · Work · Family and kids · Over text · Parties · When it dies · Topics to talk about · FAQ
The 10 best conversation starters (non-boring picks)
The best conversation starters work on almost anyone: a coworker, a date, a cousin you see once a year. These ten are safe enough for a first meeting and interesting enough to keep going for twenty minutes.
1. What’s the best thing that’s happened to you this week? (light)
2. What are you looking forward to right now, even something tiny? (light)
3. What’s something you’ve gotten weirdly good at? (light)
4. What’s a small thing that makes your day noticeably better? (light)
5. What were you obsessed with at age 12? (medium)
6. What’s a place that feels like “you”, and why? (medium)
7. What’s a rabbit hole you fell down recently? (light)
8. Who’s someone you met only once but never forgot? (medium)
9. What’s a story your family always tells about you? (medium)
10. What would you do with a free Tuesday and nobody needing anything from you? (light)
What makes a question non-boring?
A non-boring question asks for a story, not a fact. “Where are you from?” gets a city name. “What do you miss most about where you grew up?” gets a memory, an opinion and three follow-up questions for free.
Every starter on this page passes four tests:
- Open: it can’t be answered with yes, no or a single word.
- Specific: it points at one moment, place or feeling instead of “your life”.
- Low-pressure: anyone can answer it in ten seconds without feeling judged.
- Shareable: you’d happily answer it yourself, which matters, because you will.
Boring question vs. non-boring upgrade
| Boring question | Non-boring upgrade |
|---|---|
| What do you do? | What’s the best part of what you do? |
| How are you? | What’s been the highlight of your week? |
| Where are you from? | What do you miss most about where you grew up? |
| Do you have any hobbies? | What do you lose track of time doing? |
| Seen any good movies? | What did you watch recently that you couldn’t stop thinking about? |
| How was your weekend? | What was the best moment of your weekend? |
| Do you like to travel? | Where’s somewhere that surprised you? |
| What’s your favorite food? | What’s a meal you’d cross town for? |
| How’s work going? | What’s something at work you’re actually excited about? |
| Any plans for the holidays? | What’s a holiday tradition you’d never skip? |
How to start a conversation in 4 steps
To start a conversation, open with something you both share, ask a follow-up question, offer a bit of yourself, and leave on a warm note. That’s the whole method, and it works with strangers, coworkers and dates alike.
- Open with the shared moment. Comment on something you’re both experiencing (the venue, the host, the queue, the weather if you must), then attach an open question: “This place is packed. How do you know Sam?”
- Ask the follow-up. Harvard researchers found that people who asked more questions, especially follow-up questions, were better liked, and the most curious speed-daters got the most second dates (Harvard Business School Working Knowledge). “Wait, how did that start?” beats a brand-new topic every time.
- Share your own answer. A barrage of questions feels like an interview. After their answer, give yours in two or three sentences. It shows you’re playing too and gives them something to ask about.
- Exit warmly. End while it’s still good: “I’m going to grab a drink, but I want to hear how the pottery class goes.” Naming something they said is what makes them remember you.
Stuck for a topic? Use FORD: Family, Occupation, Recreation, Dreams. Move from the first two (safe) to the last two (interesting) as the conversation warms up.
Talking to strangers is usually better than we predict. In a Chicago commuter study, riders who chatted with a stranger reported a more pleasant journey than those who sat in silence, even though people surveyed beforehand expected the opposite (Chicago Booth Review).
How deep should you go? Light, medium or deep
Every question below is tagged so you can match it to the moment:
- Light: safe with anyone, answerable in a sentence. Use these for first meetings, work and group settings.
- Medium: a little personal, usually brings out a story. Use once the conversation has warmed up.
- Deep: values, memories and feelings. Use with friends, partners, or a stranger who’s clearly up for it.
A simple rule: go one level deeper than feels comfortable, never two.
Small talk questions that aren’t boring
Small talk questions are light, low-risk openers for people you’ve just met: at a party, in a waiting room, or before a meeting starts. These 25 keep it easy without falling back on the weather.
11. How do you know the host, and what’s the story there? (light)
12. What’s keeping you busy outside of work lately? (light)
13. Are you a plan-everything person or a figure-it-out-on-the-day person? (light)
14. What’s the most underrated spot in this town? (light)
15. What’s the last thing you watched that you’d actually recommend? (light)
16. Is there a food you could happily eat three days in a row? (light)
17. What’s a hobby you keep meaning to start? (light)
18. What’s your coffee order, and how long has it been the same? (light)
19. What’s the best meal you’ve had this year? (light)
20. Do you have a go-to karaoke song, or would you rather leave the building? (light)
21. What’s something about your job that people always get wrong? (medium)
22. Morning person, night owl, or somewhere chaotic in between? (light)
23. What’s the last thing you bought that turned out to be completely worth it? (light)
24. Where’s somewhere you’ve been that surprised you? (light)
25. What did you want to be when you grew up, and how close did you get? (medium)
26. What podcast or playlist is on repeat for you right now? (light)
27. Beach holiday or city holiday, and why? (light)
28. What’s a local event you never miss? (light)
29. What’s the strangest job you’ve ever had? (medium)
30. Which season do you secretly think is overrated? (light)
31. What’s an app you couldn’t live without, and one you should delete? (light)
32. What’s the best thing you’ve ever made with your hands? (light)
33. What brought you to this city, or what keeps you here? (medium)
34. What’s your favorite way to spend a rainy afternoon? (light)
35. What’s something you’re excited about that has nothing to do with work? (light)
Conversation starters for friends
Conversation starters for friends work best when they dig into shared history and the stuff you never got around to asking. Use these on a long drive, a late night in, or any evening you’d normally spend scrolling side by side at a friend’s house.
36. What’s a memory of us you think I’ve forgotten? (medium)
37. Which era of your life would you go back and visit for a day? (medium)
38. What’s something you’re proud of that you never brag about? (medium)
39. Which of our friends would you trust to plan your birthday from scratch? (light)
40. What’s a habit you picked up from me, good or bad? (light)
41. What’s a dream you quietly gave up on, and do you miss it? (deep)
42. What’s the most “you” thing you’ve done this year? (light)
43. What’s something you want to try before next summer? (light)
44. What will you be doing in five years that would shock the 2020 version of you? (medium)
45. What’s a song that instantly takes you back to one specific night? (medium)
46. Who were you trying to impress in high school? (medium)
47. Is there something you’re quietly dealing with that I could help with? (deep)
48. What would a perfect weekend away with our group look like? (light)
49. What’s a small win you haven’t told anyone about yet? (light)
50. What’s the best thing a stranger has ever done for you? (medium)
51. What’s a phase you went through that you’re secretly still in? (light)
52. What did you believe about adulthood that turned out to be completely wrong? (medium)
53. Which friend from another part of your life would get along best with me? (light)
54. What’s a tradition we should start? (light)
55. What scared you as a kid that seems hilarious now? (light)
56. What’s one thing you’d like to get better at this year? (medium)
57. What trip do we keep talking about that we should actually book? (light)
58. What piece of grown-up life have you finally figured out? (light)
59. What’s something you’re looking forward to doing alone? (light)
60. What advice would you give the version of you from three years ago? (medium)
Fun and funny conversation starters
Funny conversation starters lower everyone’s guard fast, which is exactly why they’re the best warm-up before deeper questions. If your group wants more silly hypotheticals, our would you rather questions take it further.
61. What’s the most useless fact you know by heart? (light)
62. If your life had a video-game loading screen tip, what would it say? (light)
63. What’s a food combination you’ll defend to the end? (light)
64. Which fictional character would be the worst roommate? (light)
65. What’s the most ridiculous argument you’ve ever won? (light)
66. If you were a ghost, how would you haunt people? (light)
67. What would your villain origin story be? (light)
68. Which everyday object would be terrifying if it were ten times bigger? (light)
69. What’s a word you mispronounce on purpose? (light)
70. What’s the weirdest thing you’ve ever seen on public transport? (light)
71. What’s your most irrational pet peeve? (light)
72. What’s the most dramatic way you’ve ever left a group chat? (light)
73. What’s a rule you made up as a kid that you still follow? (light)
74. Which reality TV show would you get kicked off first? (light)
75. What’s a smell that instantly puts you in a good mood? (light)
76. What’s the worst haircut you’ve ever paid for? (light)
77. What’s the most chaotic thing you’ve done to avoid an awkward conversation? (light)
78. What’s a trend you joined and instantly regretted? (light)
79. What would your autobiography be called right now? (light)
80. What’s the strangest thing you believed as a kid? (light)
81. Which snack is criminally underrated? (light)
82. What’s the funniest thing you’ve overheard in public? (light)
83. What skill would you put on your resume if honesty didn’t matter? (light)
84. Which board game reveals someone’s true personality? (light)
85. What’s the most “main character” moment you’ve ever had? (light)
20 random questions to ask anyone
Random questions work when a conversation needs a jolt: they’re unexpected, quick to answer and hard to get wrong. Need more ways to kill ten minutes online? Try our websites to cure boredom.
86. What’s a city you’ve never visited but feel like you know? (light)
87. Which decade’s fashion would you bring back? (light)
88. What’s the most interesting thing you’ve learned from a random video? (light)
89. Which historical era would you hate to live in? (light)
90. What’s the best piece of furniture you’ve ever owned? (light)
91. Do you name your plants, cars or gadgets? (light)
92. What’s a sound you love that most people find annoying? (light)
93. What would you put in a time capsule to open in 2050? (medium)
94. What’s the most impressive thing you can cook from memory? (light)
95. What’s your favorite word, and why that one? (light)
96. What would you ask an astronaut? (light)
97. Which invention do you think is overhyped? (light)
98. What’s the oldest thing you own? (medium)
99. What sport would you add to the Olympics? (light)
100. What’s your strategy at a buffet? (light)
101. What’s the most beautiful place you’ve seen in person? (medium)
102. What’s a myth you believed for far too long? (light)
103. If you opened a small shop, what would it sell? (light)
104. What’s the best view you’ve ever had from a window? (light)
105. What’s a museum you’d happily spend a whole day in? (light)
Deep conversation starters
Deep conversation starters ask about values, turning points and feelings, so save them for people who’ve shown they’re up for it. They’re also the most interesting conversation starters on this page, because almost nobody gets asked them. For a structured way to go deep with one person, try the 21 questions game.
106. What do you understand now that you couldn’t have understood five years ago? (deep)
107. What does a good life look like to you, the unglamorous version? (deep)
108. When do you feel most like yourself? (deep)
109. What’s a fear you’ve outgrown? (deep)
110. Who taught you how to be kind, on purpose or by accident? (deep)
111. When did you realize you’d changed as a person? (deep)
112. What do you want more of next year, and what do you want less of? (medium)
113. What’s a question you wish people asked you more often? (deep)
114. What have you forgiven that you never thought you would? (deep)
115. What does “home” mean to you now, compared with when you were a kid? (deep)
116. What are you still learning to let go of? (deep)
117. What’s the kindest thing you’ve done that nobody knows about? (deep)
118. What role do you usually play in a group, and is it the one you want? (deep)
119. What’s a value you’d keep even if it cost you something? (deep)
120. What’s a risk you’re glad you took? (medium)
121. Who in your life do you wish you’d thanked properly? (deep)
122. What do you think you’re here to do? (deep)
123. What are you proud of getting through? (deep)
124. How do you know when you need a break, and do you take it? (medium)
125. What belief did you inherit that you still haven’t decided whether to keep? (deep)
126. What’s the most meaningful conversation you’ve ever had with a stranger? (deep)
127. What makes you feel safe with someone? (deep)
128. Which chapter of your life would you title differently now? (deep)
129. What does success mean to you this year, not in general? (medium)
130. How do you want people to feel after spending time with you? (deep)
Conversation starters for dates and couples
Conversation starters for dating should feel curious, not like an interview. These work on a first date, a fifth date or a fifteenth anniversary dinner, and the flirty ones stay playful rather than awkward.
131. What’s your idea of a perfect lazy Sunday together? (light)
132. What’s a small gesture that makes you feel cared for? (medium)
133. What’s a date idea you’ve always wanted to try but never suggested? (light)
134. What did you think love would look like when you were a teenager? (medium)
135. What’s a place that means something to you that you’d love to show me? (medium)
136. What do you admire about couples you know? (medium)
137. Are you the one who plans everything, or the one who shows up? (light)
138. What’s a movie we should watch together that says a lot about you? (light)
139. What’s something you’re curious about that you’ve never mentioned on a date? (medium)
140. What’s the best date you’ve ever been on, even if it wasn’t with me? (medium)
141. How do you like to be comforted on a bad day? (medium)
142. What’s a family tradition you’d want to keep? (medium)
143. What’s something new you’d like us to try this month? (light)
144. Whose relationship among your friends do you secretly take notes on? (light)
145. What song would play over our first scene if we were in a movie? (light)
146. What do you need more of from me without having to ask? (deep)
147. What’s a fun fact about you that most people never find out? (light)
148. Which city should we get lost in together? (light)
149. Which of my hobbies would you actually like to try? (light)
150. What was your favorite part of today? (light)
151. What’s a dream we could chase together? (deep)
152. How does the way you were raised show up in how you love? (deep)
153. What’s one thing we do that you hope we never stop doing? (medium)
154. What are you most looking forward to in the next year? (light)
155. What’s a question you’ve been waiting for me to ask? (deep)
Work conversation starters
Work conversation starters keep things professional while still getting past job titles. Use them at networking events, team lunches or the first five minutes of a video call.
156. What project are you most excited about right now? (light)
157. Did you end up in this field on purpose or by accident? (medium)
158. What’s the best career advice you’ve ever had? (medium)
159. What does a good day at work look like for you? (light)
160. What have you learned on the job that school never taught you? (light)
161. Who have you learned the most from at work? (medium)
162. What’s one tool or habit that saves you hours a week? (light)
163. What’s the most interesting problem you’ve solved this year? (medium)
164. What’s something about your role that people outside it never see? (medium)
165. What are you trying to get better at professionally? (medium)
166. Where do you do your best thinking? (light)
167. What’s your favorite question to ask in an interview? (light)
168. What would you be doing if you weren’t in this job? (medium)
169. Which trend in your industry are you watching closely? (light)
170. What’s a win from this month you’re proud of? (light)
171. What’s the most useful meeting you’ve ever been in, and why? (light)
172. Which talk or book changed the way you work? (medium)
173. How do you switch off after a hard day? (light)
174. What’s your first-job story? (light)
175. What’s one thing that would make your week easier? (light)
Family conversation starters for dinner and kids
Family conversation starters replace “How was school?” (answer: “fine”) with questions kids actually want to answer. The first 13 suit younger kids; the rest work for teens and the whole dinner table.
For kids
176. What was the best part of your day, and the worst? (light)
177. Who did you sit with at lunch today? (light)
178. If you were the teacher tomorrow, what would you teach? (light)
179. What made you laugh today? (light)
180. If you could have any animal as a pet, what would you pick and what would you name it? (light)
181. What’s something kind someone did today? (medium)
182. If our family had a superpower, what would it be? (light)
183. What rule would you make if you were in charge of the house for a day? (light)
184. What’s something hard you tried this week? (medium)
185. If you could invent a new holiday, what would we celebrate? (light)
186. What’s your favorite thing about your best friend? (light)
187. Where would you go if you could travel anywhere tomorrow? (light)
188. What’s something you want to learn how to do? (light)
For teens and the whole family
189. What’s something adults don’t get about being your age? (medium)
190. What’s the most overrated thing everyone at school is into? (light)
191. What song goes on the family road trip playlist? (light)
192. Which family story should be told at your wedding someday? (light)
193. What’s something we should do as a family more often? (medium)
194. What did you learn this week that wasn’t on any test? (light)
195. What’s a decision you’re proud of making on your own? (medium)
196. Which family member are you most like, and are you happy about it? (light)
197. What would you change about our weekends? (light)
198. What’s a dinner we should cook together this month? (light)
199. What’s a goal you have that we could help with? (medium)
200. What’s your favorite memory from when you were little? (medium)
Conversation starters over text
Good conversation starters over text are short, easy to reply to on a phone, and give the other person something specific to react to. Send one, then actually respond to their answer before sending the next.
201. Quick one: what’s the best thing you’ve eaten this week? (light)
202. Rate your day out of 10, and explain the missing points. (light)
203. Send me the last photo in your camera roll you’d actually show someone. (light)
204. What are you procrastinating on right now? (light)
205. What song have you had on repeat this week? Send it. (light)
206. Hot take of the day. Go. (light)
207. What’s the plan for the weekend, realistic version? (light)
208. What’s one thing that would make tomorrow better? (light)
209. Describe your day in three emojis. (light)
210. What are you looking forward to this month? (light)
211. What show should I start tonight? (light)
212. Tell me one small win from today. (light)
213. What’s the most random thing you’ve thought about today? (light)
214. What’s your comfort meal right now? (light)
215. What memory randomly popped into your head this week? (medium)
216. If we hung out tomorrow, what would we do? (light)
217. What’s something you’ve been meaning to tell me? (medium)
218. What’s the best thing you’ve read or seen online this week? (light)
219. What’s been on your mind lately, honestly? (medium)
220. Morning check-in: coffee, tea, or pure willpower? (light)
Texting late? Pair these with our list of things to do when you’re bored at night.
Party conversation starters for groups
Party conversation starters give a whole group something to answer at once, which beats the awkward pairs that form by the snack table. When the group wants a structured game instead, switch to truth or dare, never have I ever or paranoia, or browse our games to play when bored.
221. What’s the best party you’ve ever been to, and what made it work? (light)
222. Who here has the best story about how they met the host? (light)
223. What’s a hobby you could teach this group in ten minutes? (light)
224. What’s the best concert you’ve ever been to? (light)
225. What dish would you bring to win a potluck? (light)
226. What underrated movie would you make everyone here watch? (light)
227. What’s the best trip you’ve taken with a group? (light)
228. What childhood game should we bring back tonight? (light)
229. What song gets you on the dance floor every single time? (light)
230. Everyone: one thing on your list for next year. (light)
231. Whose skill in this room would you swap for one of yours? (light)
232. What’s the best gift you’ve ever received? (light)
233. What’s a book everyone here should read? (light)
234. What’s a city everyone here needs to visit? (light)
235. What’s the funniest thing that happened to you this year? (light)
How to keep a conversation going: 15 rescue lines
To keep a conversation going, ask about what the other person just said instead of changing the subject. These questions to keep a conversation going work on almost any answer, in person or over text.
236. Wait, go back. How did that start? (light)
237. What happened next? (light)
238. What was the best part of that? (light)
239. How did you get into that in the first place? (light)
240. Would you do it again? (light)
241. What surprised you most about it? (medium)
242. What’s the story behind that? (light)
243. How did that change things for you? (medium)
244. What would you tell someone about to try it? (light)
245. What’s something about that most people don’t realize? (light)
246. Who else was there? (light)
247. What was going through your head at the time? (medium)
248. What do you want to do next with that? (light)
249. Did it turn out how you expected? (light)
250. What’s your favorite part of doing it now? (light)
Topics to talk about (with a non-boring angle)
The easiest topics to talk about are the ones everyone has an opinion on: food, travel, entertainment and small daily wins. The trick is the angle. Each conversation topic below has a question that turns it from a fact into a story.
| Topic | Non-boring angle | Works best with |
|---|---|---|
| Food | “What’s a meal you’d cross town for?” | Anyone |
| Travel | “Where’s somewhere that surprised you?” | New people, dates |
| TV and movies | “What did you watch that you couldn’t stop thinking about?” | Anyone |
| Music | “What song takes you back to one specific night?” | Friends, dates |
| Books | “What book would you hand to a stranger?” (ideas here) | Friends, coworkers |
| Childhood | “What were you obsessed with at 12?” | Anyone once warmed up |
| Work | “What’s the best part of what you do?” | Networking, coworkers |
| Hobbies | “What do you lose track of time doing?” | Anyone |
| Hometown | “What do you miss most about where you grew up?” | New people |
| Goals | “What do you want more of next year?” | Friends, partners |
| Pets | “What’s your pet’s most human habit?” | Anyone |
| Hypotheticals | “If you opened a small shop, what would it sell?” | Groups, kids |
Topics to avoid with someone you just met: money and salaries, weight and bodies, exes, and hot-button politics or religion. They’re not off-limits forever, just not for the first ten minutes.
More ways to beat boredom with good company
A great question is the cheapest entertainment there is. When the conversation is flowing, keep the night going with our would you rather questions or the full list of things to do when bored.
Conversation starters FAQ
What are good conversation starters?
Good conversation starters are open-ended questions about specific moments, such as “What’s the best thing that’s happened to you this week?” or “What’s something you’ve gotten weirdly good at?” They work because anyone can answer them with a short story, which gives you something natural to follow up on.
What are the top 10 conversation starters?
The top 10 conversation starters for almost any situation are listed at the top of this page. Five favorites: “What’s the best thing that’s happened to you this week?”, “What were you obsessed with at age 12?”, “What’s a rabbit hole you fell down recently?”, “Who’s someone you met only once but never forgot?” and “What would you do with a free Tuesday?”
What are 20 random questions to ask?
Random questions are unexpected but easy to answer, like “What’s the oldest thing you own?”, “Which invention is overhyped?” or “What would you put in a time capsule to open in 2050?” The full set of 20 random questions is in the fun section above (numbers 86 to 105).
What are good flirty conversation starters?
Good flirty conversation starters are playful and curious rather than forward. Try “What’s a date idea you’ve always wanted to try but never suggested?”, “Which city should we get lost in together?” or “What song would play over our first scene in a movie?” They signal interest without putting anyone on the spot.
How do you keep a conversation going?
Keep a conversation going by asking about what the person just said, not by changing the subject. Follow-up questions like “How did that start?” or “What surprised you most?” show you’re listening, and research from Harvard links follow-up questions to being better liked.
How do you start a conversation with a stranger?
Start a conversation with a stranger by commenting on something you’re both experiencing, then asking an open question about it, such as “This place is packed, how do you know the host?” Keep your first question light, and share a little about yourself once they answer.
What should you not talk about with someone you just met?
Avoid money, weight, exes, and divisive politics or religion with someone you just met. Those topics ask for trust that hasn’t been built yet. Stick to light and medium questions until the other person starts sharing more on their own.
Using these on a date? Pair them with one of our date night ideas.
Need an icebreaker that always gets a reaction? Open with one of these corny jokes; the groan does the work for you.
Ready to go beyond small talk? Our guide to questions to get to know someone sorts 267 fresh questions into five layers, from easy openers to deep ones, with a card tool that draws one for you.
What’s the difference between small talk and a conversation starter?
Small talk fills silence with safe facts like the weather or the commute. A conversation starter invites a story or an opinion, which gives the other person something to say and you something to ask about next. The best starters begin light and leave room to go deeper.
