281 Conversation Starters​ To Take the "Awkward" Out in 2025

Sometimes, you need conversation starters to get you out of an awkward chat and into a fun or meaningful discussion. You can use these conversation starters as a way to break the ice and prompt insightful or even ridiculous conversations. These work in a group, at school, with your partner or at your next forced family gathering. 

The trick is to pick the right conversation starter for your scenario. Are you looking for deep questions to ask or funny questions to ask? Pick the type of question that aligns with your desired conversation mood. 

Jump to Section

• Good Conversation Starters​
• Deep Conversation Starters​
• Best Conversation Starters​
• Conversation Starters For Couples​
• Great Conversation Starters​
• Funny Conversation Starters​
• Weird Conversation Starters​

Good Conversation Starters​

What's a good convo starter? Well, you need something better than random questions to ask when trying to get a good conversation started. Truly good conversation starters don't just prompt a simple answer. They are interesting enough or complicated enough that they can lead you on a fun, but not too intimate, conversation. These are the questions to whip out when you’re:

• Stuck at a work function
• Sat with strangers at a wedding reception
• Playing icebreakers with your church group
• Halfway through a semi-boring first date

Honestly, you can use these conversation starters anywhere, but they're designed for when you're trapped somewhere and need a good, basic conversation. Write a few down and be prepared for anything.

1. What’s the most interesting thing you’ve read or seen this week?

2. What’s your go-to comfort food?

3. Have you been on any fun trips lately?

4. What kind of music are you into right now?

5. Do you have a favorite podcast or show?

6. What’s your favorite way to spend a day off?

7. Do you prefer coffee or tea — and how do you take it?

8. What’s your favorite holiday tradition?

9. What book would you recommend to everyone?

10. Are you more of an early bird or a night owl?

11. Do you enjoy cooking or baking more?

12. What’s a fun fact not many people know about you?

13. Have you picked up any new hobbies lately?

14. What’s your favorite way to relax after a long day?

15. What’s your favorite movie of all time?

16. Do you have a favorite childhood memory?

17. What was your first job?

18. What’s one item on your bucket list?

19. Do you have a favorite local restaurant?

20. How do you usually spend your weekends?

21. Have you ever met anyone famous?

22. What’s your favorite app on your phone?

23. Do you like attending concerts or prefer quiet nights?

24. What’s your favorite dessert?

25. Are you more into fiction or nonfiction?

26. What sport or game do you love watching or playing?

27. What’s a dream vacation destination for you?

28. Do you prefer texting or phone calls?

29. Do you collect anything? If so, how long have you been collecting?

30. What’s a TV show you could rewatch over and over?

31. What’s your favorite board or card game?

32. Do you like planning or being spontaneous?

33. What motivates you in the morning?

34. What’s your favorite way to stay active?

35. What’s a hobby you’d love to try?

36. Do you prefer beaches or mountains?

37. What’s your favorite animal and why?

38. If you had to eat one food for the rest of your life, what would it be?

39. What’s your go-to karaoke song?

40. What’s the last thing that made you laugh?

Deep Conversation Starters​

Wondering how to start a deep talk? Some conversations should go way beyond "wow, the weather is great" and "my weekend is busy." More intimate conversations should tap into who we are, what we value and how we see the world. These deep conversation starters are for the moments when you're ready to open up or get to know someone on a real, honest level. 

These aren't the questions to whip out at a work picnic, though some could double as excellent interview questions. They're perfect for long walks with a best friend, quiet evenings with your partner, or moments of personal introspection. These questions are built to create space for depth and insight. Just don't be surprised if you learn something big, or beautiful, about someone or yourself along the way. Also, for some of these questions, don’t forget to bring the tissues and get ready to give a hug. 

41. What does success mean to you?

42. What’s a moment that changed your life?

43. How do you handle failure?

44. What are you most grateful for right now?

45. Do you believe everything happens for a reason?

46. How do you define happiness?

47. What’s something you’ve never told anyone?

48. What legacy do you want to leave behind?

49. What do you think makes a meaningful life?

50. Have you ever had your heart broken?

51. What scares you the most?

52. Do you believe people can change?

53. What do you value most in friendship?

54. What’s your biggest regret?

55. How do you recharge when you feel drained?

56. What role does faith or spirituality play in your life?

57. How do you deal with uncertainty?

58. What's something you're still learning about yourself?

59. How do you express your vulnerability?

60. Have you ever had a mentor who changed your life?

61. What's one lesson you learned the hard way?

62. What do you admire most in others?

63. Do you forgive easily?

64. When do you feel most like yourself?

65. What's your biggest fear for the future?

66. What's one dream you've let go of?

67. What brings you peace?

68. What's something you wish more people understood about you?

69. Do you believe people are inherently good?

70. How do you make difficult decisions?

71. What's your relationship like with your inner critic?

72. When have you felt the freest?

73. What's a belief you've outgrown?

74. What gives your life purpose?

75. What's your personal definition of love?

76. What part of your past do you revisit most?

77. How do you want to be remembered?

78. What does vulnerability look like to you?

79. When was the last time you truly felt seen?

80. Who has had the most significant impact on your life?

81. What's your greatest strength?

Best Conversation Starters​

Are you looking for the absolute best questions to get people really talking? Think long, fun conversations that seem like they're never going to end. These are the conversations that make friendships and build relationships. If you're interested, then this list is your golden ticket. These conversation starters are like the "greatest hits" album of social connection. They're crowd-pleasers that bring out smiles, stories and surprises. 

When navigating a new group or trying to make a lasting, positive impression, these questions are designed to work almost anywhere. They strike the perfect balance between easy-going and interesting, so you can skip the awkward pauses and dive into real talk. These are the questions you'll find yourself going back to repeatedly because they work and make people feel seen and at ease.

82. If you could live anywhere, where would it be?

83. What’s your favorite memory ever?

84. What’s your dream job?

85. What’s your favorite guilty pleasure?

86. If you won the lottery tomorrow, what would you do?

87. What’s the best compliment you’ve ever received?

88. What’s one thing on your bucket list?

89. Do you believe in fate or free will?

90. If you could meet any historical figure, who would it be?

91. What's your favorite way to treat yourself?

92. Do you prefer dogs or cats — and why?

93. What would your ideal weekend look like?

94. What's a skill you wish you could master instantly?

95. If you had a personal motto, what would it be?

96. What’s your most-used emoji?

97. What song always lifts your mood?

98. What’s your go-to meal to cook?

99. Who knows you best in the world?

100. What’s your favorite quote?

101. What do you do when you’re feeling stuck?

102. What do you think makes a great friend?

103. What’s one app you can’t live without?

104. What’s a movie that never gets old?

105. What's a product or service you swear by?

106. What's your favorite childhood cartoon?

107. What do you miss about being a kid?

108. If you could switch lives with someone for a day, who would it be?

109. What's your dream concert lineup?

110. What's the weirdest food you've tried?

111. What's your biggest passion?

112. What's something you want to learn this year?

113. What motivates you to keep going?

114. What's a superpower you wish you had?

115. Do you like surprises?

116. What's your proudest accomplishment?

117. How do you celebrate your wins?

118. What's something you always carry with you?

119. What's your ideal way to spend a rainy day?

120. Who's your favorite fictional character?

Conversation Starters For Couples​

Relationships thrive on communication but not every day can be a deep heart-to-heart or a candlelit dinner. You and your partner are constantly juggling work and stress and friends and family. So, these conversation starters for couples are designed to spark connection in the intimate moments and the everyday, in between bites of dinner or while lounging on the couch. 

Some are sweet, some are silly, some are steamy and some might lead to more profound discoveries about your partner (and maybe even yourself). Some of these conversation starters are better for couples who have been together longer, but some are basic fun that can spark curiosity and laughter in your day. Use them to reminisce, plan the future, or enjoy a fresh way of saying, “Tell me more.”

121. What first attracted you to me?

122. What's your favorite memory of us?

123. How do you define love?

124. What's something new you want to try together?

125. What makes you feel most loved?

126. Where would you love to travel together?

127. What's a silly habit I have that you secretly like?

128. How do you see our future?

129. What's your favorite date we've been on?

130. What's something you admire about me?

131. What's your love language?

132. What do you think we do well as a couple?

133. How has being together changed you?

134. What are your favorite things we do as a team?

135. Do you believe in soulmates?

136. What's a tradition you'd love to start?

137. How do you feel about our communication style?

138. What's something you're afraid to tell me?

139. How can I be a better partner?

140. What does intimacy mean to you?

141. When do you feel closest to me?

142. What's a memory you hope we never forget?

143. What's something you wish we did differently?

144. How do you feel when we're apart?

145. What's your idea of a romantic night in?

146. What scares you most in a relationship?

147. What do you admire about other couples?

148. What's something you never get tired of doing with me?

149. If we wrote a book together, what would it be about?

150. What's your favorite way to be comforted?

151. How do you want to grow together?

152. What's your favorite physical feature of mine?

153. What's your favorite way to show love?

154. What's your biggest dream for us?

155. What's something we've overcome together that made us stronger?

156. How do you want to celebrate our next anniversary?

157. What's one thing I do that makes you smile every time?

158. What do you love most about our life together?

159. What's a song that reminds you of me?

Great Conversation Starters​

You know those questions that make someone’s eyes instantly brighten or start you on a long, winding, thrilling conversation? That's the power of a truly great conversation starter. This section is filled with prompts that are just thoughtful or fun enough to stand out without trying too hard. They work anywhere and everywhere people want to connect. Keep a few in your back pocket. You never know when a great conversation is just a question away, especially when you put down the phone and really engage with people. 

160. What's one thing you're really good at?

161. What's something people always ask you for help with?

162. What's your favorite way to celebrate?

163. What's a movie you think everyone should watch?

164. What's a random goal you've always had?

165. If you had unlimited time, what would you do?

166. What's something that instantly improves your day?

167. Do you believe in luck?

168. What's your hidden talent?

169. What's a cause you care deeply about?

170. Do you prefer city life or country living?

171. What's something you wish you could relive?

172. How do you define a good life?

173. Who in your life makes you feel the most energized?

174. What's a tradition you want to pass down?

175. What's something worth splurging on?

176. What's a quality you admire in others?

177. What motivates you to keep learning?

178. What's the best gift you've ever received?

179. What's a story from your life you love telling?

180. What's your dream creative project?

181. What's a book or movie that changed your perspective?

182. What's a life lesson you've learned recently?

183. If you could live in any time period, what would it be?

184. What's your favorite way to connect with people?

185. What's something you hope to do next year?

186. What's your ideal vacation?

187. Who's someone you'd love to meet?

188. What's your favorite simple pleasure?

189. What's something you wish people talked about more?

190. What's a memory that always makes you laugh?

191. What's your favorite weekend activity?

192. What's a game you're surprisingly competitive at?

193. What's something that makes you feel nostalgic?

194. Do you believe in coincidences?

195. What's a quote that's stuck with you?

196. What's your favorite way to relax?

197. What would your autobiography be titled?

198. What's a challenge you're proud of overcoming?

199. What's a dream you've had more than once?

Funny Conversation Starters​

Laughter is one of the quickest ways to break the ice and can actually have tangible benefits. The Mayo Clinic reports that a good sense of humor can't cure all ailments, but laughter can stimulate organs, relieve stress, soothe tension, improve the immune system, relieve pain and improve our mood.

These funny conversation starters are the ideal way to get a laugh and all the powerful benefits mentioned before. They’re quirky, unexpected and often delightfully weird in the best way possible. Use them with friends or even your date to keep things playful. 

Some answers may cause uncontrollable, belly-aching laughter and the kind of bonding you can’t plan. Nothing brings people together quite like a shared laugh.

200. If animals could talk, which one would be the rudest?

201. What fictional character do you think would be a terrible roommate?

202. What's your go-to karaoke disaster song?

203. If you were a villain, what would your evil laugh sound like?

204. What's your most irrational fear?

205. What's the silliest thing you believed as a kid?

206. If you had to live in a sitcom, which one would it be?

207. What's the worst haircut you've ever had?

208. If your life were a reality show, what would it be called?

209. What's the dumbest thing you've Googled?

210. What would your drag name be?

211. What's the worst advice you've ever gotten?

212. What's something you pretend to understand?

213. What animal do you secretly think you resemble?

214. What's your guilty pleasure TV show?

215. What's the weirdest compliment you've ever received?

216. What would your superhero weakness be?

217. If you had to wear one outfit forever, what would it be?

218. What's the strangest gift you've ever received?

219. If you were a flavor, what would you be?

220. What's your party trick?

221. What's the most awkward moment you've ever had?

222. If you could turn into an object for a day, what would it be?

223. What's your worst cooking fail?

224. If you had a signature dance move, what would it look like?

225. What's the most embarrassing thing you've done on a date?

226. What's your weirdest habit?

227. What word do you always mispronounce?

228. Have you ever sent a text to the wrong person?

229. If your pet could talk, what would it say about you?

230. What's your best celebrity impression?

231. What's something you tried once and failed at miserably?

232. What fashion trend do you wish never happened?

233. If your life had a laugh track, when would it go off most?

234. What's your most unpopular opinion?

235. What's the worst pickup line you've heard or used?

236. What would your "useless talent" be in a talent show?

237. What would be your strategy in a zombie apocalypse?

238. What's the most ridiculous fear you've overcome?

239. If aliens came tomorrow, what would you show them first?

Weird Conversation Starters​

Do you remember late-night sleepover conversations when you and your friends were giddy and giggly and you had the strangest, bizarre conversations? These are the questions you need to bring to the table when you're looking to replicate that feeling. How do you start a fun talk? With these weird conversation starters. 

They're offbeat, unexpected, and just the right amount of strange to jolt you out of a typical back-and-forth. So embrace the weird, ask the question, and watch as conversations go from zero to "What if clouds had personalities?" faster than you can say "telepathic potato." (You'll get it as you read these super weird questions.)

240. If you had to swap bodies with an animal, what would it be?

241. What would you name your pet dinosaur?

242. If you woke up invisible, what's the first thing you'd do?

243. What color do you think smells the best?

244. Would you rather fight 100 duck-sized horses or one horse-sized duck?

245. If you could eat a cloud, what do you think it would taste like?

246. What's your conspiracy theory of choice?

247. Do you think aliens wear clothes?

248. Would you live in a haunted house for a million dollars?

249. What would a telepathic potato say to you?

250. If you could invent a new sense, what would it be?

251. If your life had a smell, what would it be?

252. Could you survive a week without your phone?

253. What would your imaginary friend be like?

254. Would you rather have spaghetti hair or marshmallow feet?

255. What's a word that sounds fake to you?

256. Would you eat food that glowed in the dark?

257. If animals ruled the world, who would be president?

258. What's something you'd say to your clone?

259. What's your dream cryptid encounter? [A cryptid is an animal whose existence or survival is disputed or unsubstantiated, like the yeti.]

260. If your shadow had a personality, what would it be like?

261. What food do you think has feelings?

262. What shape is your aura?

263. What would a fortune cookie from the future say?

264. If you had to wear one costume forever, what would it be?

265. What smell brings back the weirdest memory?

266. Could you live in a submarine for a year?

267. What's the most ridiculous fear you had as a child?

268. What would your cursed superpower be?

269. Would you live on the moon if it had pizza?

270. What would chairs say if they could talk?

271. Do you think ghosts have hobbies?

272. What's the strangest way you've met someone?

273. If time were a flavor, what would it taste like?

274. What mythical creature do you wish existed?

275. If you had a pet rock, what would you name it?

276. Would you go to a concert where plants performed?

277. What would your evil twin do that you wouldn't?

278. If clouds could text, what would they say?

279. What's the creepiest thing you believed as a kid?

280. If your reflection winked at you, what would you do?

281. Which Ninja Turtle would you be? 

Being armed with the right question can make all the difference in a potentially awkward conversation. Whether you need questions to ask a guy or questions to ask a girl, these conversation starters are here to help you go beyond small talk. Let’s ditch the awkwardness and lean into curiosity, authenticity and a little bit of fun. Because the best connections often start with a simple question.

For even more fun ways to start a conversation, check out the experiences happening on Classpop!