300 Interesting First Date Questions That’ll Get the Conversation Going

First Date Questions

– First Date Questions –

There are so many first date questions that you’ll never run out of topics to discuss. Choose the questions that are most appropriate for you and your date.

First Date Questions

First dates may be thrilling, especially if you sense a special spark as soon as the date begins. But romance is much more than simply attraction; it’s also about getting to know one other.

There are a plethora of methods to get to know one another, but none of them are as simple as asking one other some entertaining first-date questions!

With that in mind, here are 300 questions to have in your back pocket in the event you get a second date.

Good First Date Questions

1. What is your favorite film in the comedy genre?

2. Do you think you’ll call me after this date or run a mile?

3. What was the first book you read that really stuck with you?

4. What is the aspect of dating that you hate the most?

5. Do you have a favorite piece of art or artist?

6. What’s the state of your social life?

7. Who from the same sex do you admire?

8. How do you spend a typical day?

9. What are your obligations and how long have you been doing them?

10. Do you have any particular passion projects that you’re working on?

Questions to Ask on a First Date

11. What is your favorite international food?

12. What kind of pet have you ever had since you were a child?

13. Do you hang out with a large group of people?

14. Who are the people in your life who have a special place in your heart?

15. What was your favorite family vacation when you were a kid?

16. What do you think were you like as a kid?

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

18. Did you participate in any sports as a child?

19. What is one activity that you would like to do on a date?

20. What do you usually like to do in your free time?

First Date Questions

Questions to Ask on First Date

21. What’s your favorite hangover food?

22. Are you an introvert or an extrovert?

23. What’s something you’d like to learn or be better at?

24. What is something you’ve always wanted to do but were afraid to?

25. What are you obsessing about these days?

26. Do you feel like you could fall in love tonight?

27. What’s the longest lie-in you have ever had?

28. Do you talk to your pets? What do you say to them?

29. If you could drink one alcoholic drink and not get drunk, what would it be?

30. Do you think I look the same as my social media profile picture?

Best First Date Questions

31. If you had 48 hours to live, how would you spend it?

32. How long could you survive without your phone?

33. If you had to choose a song to describe your life right now, what would you choose?

34. Are you feeling butterflies in your stomach right now?

35. What’s on your mind right now about this date?

36. Do you fancy going on a big adventure with me?

37. Do you think dogs or cats are more intelligent?

38. Do you know how incredible your eyes are?

39. What’s the funniest injury you have ever been to the hospital with?

40. How many Cheetos do you think you could fit into your mouth?

Flirty First Date Questions

41. If you could switch places with anyone in the world for a day, who would it be, and what would you do?

42. Have you ever had somebody call you the wrong name and not had the heart to correct them? If so, what did they call you?

43. What’s the weirdest thing you have ever done that makes you feel embarrassed to talk about?

44. What was your very first impression of me, in one word? Don’t hold back!

45. Have you ever been in a food fight?

46. What item of clothing do people wear that you wouldn’t be seen dead in?

47. What’s the last thing you got the giggles over that you really shouldn’t have?

48. Why are you still single?

49. Are you a hopeless romantic, or are you a tough nut to crack?

50. If you could switch genders today, what would be the first thing you’d do?

Good Questions to Ask on a First Date

51. Have you ever pretended to have a good time when you’ve not enjoyed yourself?

52. What’s the most embarrassing thing you have ever done?

53. Where could we go after this?

54. What would you call yourself if you were a DJ?

55. What’s the craziest thing you have ever done in the name of love?

56. What would be your chosen superpower?

57. Do you have any male friends, and if so, what interests do you have in common with them?

58. Which animal do you think is the biggest party animal?

59. What alcohol has a smell that reminds you of the night you almost died?

60. How many donuts can you stuff into your mouth at the same time?

Deep Talk

Deep First Date Questions

61. What do you do if you’re on a plane that’s going down and there’s just one parachute for you and your wife/husband or girlfriend/boyfriend?

62. Do you believe your zodiac sign and birth chart describe you?

63. Which cartoon character do you think you most resemble?

64. Will you prefer to live in a vending machine or be one?

65. What do you think a caterpillar would taste like?

66. What do we all do as humans that seem to be ridiculous?

67. What was the funniest injury you’ve ever suffered?

68. What would peanut butter be called if it had a different name?

69. What is one thing you will never wear outside?

70. Who would you like to swap places with if you could?

First Date Questions Funny

71. How much do you wish you could simply set yourself on fire each day?

72. Do you believe that dogs and cats have any regrets?

73. What’s the most ridiculous thing you’ve ever done in the name of love?

74. Do you enjoy grocery shopping?

75. How do you usually put on your toilet roll?

76. What is the weirdest place you’ve ever been?

77. Do you have any tattoos? If so, what’s the meaning behind it?

78. What’s the most embarrassing thing you’ve ever looked up on Google?

79. What types of music do you enjoy listening to?

80.  How long have been living in this city?

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First Date Questions to Ask

81. What is your favorite pastry to bake?

82. What’s the most embarrassing thing you’re afraid of?

83. Who’s the first celebrity you were attracted to when you were a child?

84. What’s the weirdest thing you did as a child that you’re embarrassed by today?

85. Would you prefer to ride a rollercoaster or visit a haunted house?

86. Are there any accents you’re able to mimic? Can I hear your impression?

87. What’s the worst nickname someone has ever called you?

88. What’s the worst joke you’ve ever told to someone?

89. What’s the longest amount of time you would leave food on the floor before it was too late to eat it?

90. Which famous figure do you find attractive that most people aren’t into?

Questions for First Date

91. What’s the stupidest thing you’ve done to impress someone you like?

92. Have you ever been on the receiving end of a practical joke?

93. Have you ever sent a text or email to someone you were bitching about by accident?

94. What’s the most embarrassing thing to happen to you on a first date?

95. Have you ever fancied a cartoon character? If so, who?

96. Have you ever drunk texted anybody you wish you shouldn’t have?

97. How old would someone have to be for you not to date them?

98. If you had to pick one song to perform at karaoke, which one would you choose?

99. Have you ever been in a situation where you needed to make others laugh?

100. What’s the longest you’ve gone without picking up and consuming food that’s been dropped on the floor?

Awesome Talks

Fun First Date Questions

101. Have you ever spat in another person’s food?

102. Are you currently accepting applications for a boyfriend/girlfriend?

103. Could you survive without your phone for the rest of your life?

104. What would you be if you had to be an item for a month?

105. What would your nickname be if you were a boxer or a UFC fighter?

106. Have you ever argued with your best friend over the same boy or girl?

107. Have you ever texted a complete stranger just for fun?

108. What abilities do you possess that will help you in surviving a zombie apocalypse?

109. If you only had 48 hours to live, what are the things you would do?

110. Why did Cinderella’s shoe fall off if it fit perfectly?

Questions for a First Date

111. How many times have you attempted telepathic communication with a dog just to see if you could?

112. Do you believe the cats are plotting against us?

113. How many days in a row do you wear the same pair of pants before it becomes a problem?

114. What do you think am I thinking about right now?

115. Have you set up a hidden code with a friend to get out of this date if things go wrong?

116. How much longer are you going to sit in pain rather than get up and get a remote that’s out of reach?

117. How long does it take you to finish your bucket of popcorn during the first movie theater preview?

118. How much fried chicken do you enjoy?

119. What is your most favorite website?

120. Would you rather maintain your 18-year-old mind or body if you lived to 100?

Best Questions to Ask on a First Date

121. Which Halloween costume is the most appropriate for your personality?

122. What’s your favorite website?

123. Why do banks have branches if money doesn’t grow on trees?

124. What would you do if you were on your own and wanted to do something fun?

125. Where do you think your friends or family would be shocked to find you?

126. What nickname would be perfect for you, and why?

127. What is something that the majority of people haven’t done but that you have?

128. What was the largest group of people you have had to present anything to?

129. What one physical and non-physical aspect of yourself would you change if you could?

130. What are five things that you believe a couple should never do before getting married?

Awesome Questions

131. Do you like men’s cologne or do you find it to be overpowering? Do you have a favorite scent?

132. What apps would you keep if you had to uninstall all but two from your smartphone?

133. What would you say in just two words to your younger self if you could write a letter to yourself?

134. Who would you invite to a dinner party if you could invite ten people, dead or alive, and why?

135. What age would you want and what would the letter say if you could send one letter to yourself in the past without the goal of being rich?

136. What advice would you give to someone, if you could tell them just one thing?

137. When you’re with strangers, how do you act differently than when you’re with people you know?

138. What would you do if you found a briefcase filled with $3 million in $100 bills in front of your door?

139. What are three cities in the United States where you will never, ever consider relocating, even though you were offered the work of your dreams?

140. When would you like to go back in time as an observer, where no one could see you and you couldn’t interact with anything?

Funny Talks

Funny First Date Questions

141. What is your favorite piece of clothing?

142. Have you ever been in a toxic relationship?

143. What do you like about your current boss?

144. Can you share some funny stories of your childhood?

145. For a year, you must wear a T-shirt with one word on it. Which word would you pick?

146. What dating advice would you give to yourself back in high school?

147. Do you like it when a guy opens doors or takes your chair out for you?

148. Which of your current books would you keep if you could just keep one?

149. Which inanimate object would be the most annoying if it played noisy, upbeat music while in use?

150. What was usually inside your high school locker?

Personal Questions

151. What would you eliminate from your daily routine if you could, and why?

152. Can you tell me which city you are in without telling me which city you are in?

153. What are the red flags to watch out for in your everyday life?

154. Which one do you prefer: cry for someone you love or cry with someone you love?

155. What are the questions you would job interview your partner before you two get married?

156.  What animal would be the cutest if it was reduced to a cat’s size?

157. Where would you like to live if you had five houses to choose from around the world?

158. Would you rather spend the rest of your life single or marry someone your parents want for you?

159. What would you bring home from this place, if you could just take one thing?

160. Have you tried any unusual dishes?

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Interesting Questions

161. How did you survive the COVID-19 pandemic?

162. Would you rather win $100,000 or let your best friend win $1,000,000?

163. Do I have the same appearance in real life as you thought I would?

164. Do you like being a part of a large family, being an only child, or having an older sister, etc.?

165. If you had a robot that could only do one thing, what would it do?

166. What do you usually keep inside the trunk of your car?

167. Who would you choose if you had to choose between living with someone who really loves you but doesn’t love you back and living alone for the rest of your life loving someone who doesn’t love you?

168. Would you choose to pursue true love or win $50 million?

169. What would you change in your life if you knew you were going to die in a year?

170. What is something you wish more people knew about you, but you’re glad it’s internalized so being able to sit on this information makes you stronger?

Juicy Questions to Ask a Guy

171. Do you have something planned for the future? Or should I help in making them?

172. Will you join your partner in doing something you don’t like or enjoy?

173. When was the last time you sang aloud to yourself or to another person?

174. What would your dream bar look like if you could build it yourself?

175. Which law would you change if you had the power to do so?

176. Will you think I was asking you a trick question if I asked you if I could do anything different about my hair?

177. If we were just going to talk, where would you take me on a date?

178. How do you handle not having your phone with you for an extended period of time?

179. How many kids do you want in the future?

180. Would you mind if I paid for both of our meals, or would you prefer that we each pay for our own?

Conversation Starters

Good Questions to Ask a Girl

181. What New Year’s resolution would you like to keep?

182. What do you believe people take the most for granted?

183. Is there a documentary or book that has had a significant impact on the way you think about something?

184. When was the last time you completed a task on your to-do list?

185. What was a situation that you felt was bad at first but turned out to be a blessing in disguise?

186. If you had the time and money, what hobbies would you pursue?

187. What have you done in the last year that has forced you to step outside of your comfort zone?

188. Can you tell me about something you’ve recently accomplished that you’re most proud of?

189. Do you agree with the outcome of any personality tests you’ve taken?

190. Have you ever had a change of heart about something you were once certain of?

Questions to Ask a Girl you Like

191. What’s your Myers-Briggs personality type?

192. What would be the perfect birthday present from someone who knew you well?

193. What have you really wanted to learn more about but haven’t had the time?

194. Where did you think you’d be today five years ago?

195. What is the best Disney film that has come out since Disney’s Golden Age, in your opinion?

196. Is your family still residing in the home where you grew up?

197. Do you celebrate your birthday? And, if so, in what way? If not, does it irritate you when others do it?

198. What is the longest sleep you’ve ever had?

199. Where would you take me if you won a trip for two to anywhere in the world?

200.  Do you think you’ve always wanted to do what you’re doing now?

Get-to-Know-You Questions

201. What would you eat if you had to eat just one meal for the rest of your life until you became sick?

202. What are your thoughts on the country’s current political situation?

203. Would you rather eat a handful of bees or poison ivy?

204. What are you looking forward to the most next week?

205. What is your go-to alcoholic and non-alcoholic beverages?

206. What qualities do you want in a partner?

207. What do you eat to make you feel better?

208. When you were a child, what TV shows did you watch?

209. Do you prefer the indoors or the outdoors, or do you like both equally?

210. If we shouldn’t eat at night, why is there a light in the fridge?

Unique Questions

211. Among all of your friends, what are you best known for?

212. What city did you grow up in?

213. Do you have a best friend? How did you meet him/her?

214. Have you ever had to remove someone from your life?

215. What really makes you unique?

216. What TV series do you find yourself returning to and re-watching?

217. Is there a food you don’t eat?

218. Do you like podcasts?

219. When and what time were you born?

220. What made you fall in love with one of your favorite musicians in the first place?

Family Talks

Comfortable Questions

221. What is something that people are always surprised to learn about you?

222. What is the style of your ideal home?

223. What do you normally do when you’re feeling shy and insecure?

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

225. Do you have any siblings? If so, how many do you have?

226. What are two albums that have helped to define or mold you as a person?

227. Did your parents send you to music lessons?

228. Do you have any dating horror stories?

229. Can you tell me the experience you had when you first learned how to cook?

230. Which one do you prefer on a cold, rainy night: coffee or tea?

Conversation Starters

231. Is the glass half-full or half-empty in your eyes?

232. Do you practice what you’re going to say before making a phone call?

233. Have you long wanted to be a famous celebrity?

234. If your body would get kicked by a horse, which part would it be?

235. Do you want to order the same thing every time you go out to a restaurant or do you like to try new things?

236. What is the most stunning view you’ve ever seen?

237. What do you think would be your musician band name?

238. Would you rather get fresh flowers or fresh fruits?

239. What sports would be the most humorous if the athletes had to play while drunk?

240. What is it about people that drive you insane?

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Personality Questions

241. Have you ever tried to drop a class?

242. Have you ever been a part of a meetup group?

243. What television show would you like to live in if you could?

244. What do you imagine the world will be like in 70 years?

245. What is the best year ever?

246. What was your most recent charitable act?

247. What is the most horrible film you’ve ever seen?

248. What is one thing you wish you had learned as a college freshman?

249. What was the most recent book you finished without missing any chapters?

250. What is your all-time favorite piece of furniture?

Family Questions

251. When was the last time you went for a long walk?

252. Have you ever gotten into a fight at school?

253. What’s the ugliest animal for you?

254. What is the most enjoyable scenario you can think of?

255. What is something you’re currently saving up for?

256. What topping combinations do you think make the best pizza?

257. What would be the first thing you’d do if you didn’t have any fears?

258. What’s the longest word you’ve ever heard?

259. What’s currently in your freezer?

260. What was the last thing you have Googled?

Questions About Values

Questions about Values

261. Which cheesy pick-up line is your favorite?

262. Have you ever gone to the cinema alone?

263. What will your autobiography’s title be?

264. What are the most exciting adventures you’ve ever had?

265. What do you want to do after this?

266. What five cities in the world would you like to live in, and why?

267. Have you recently visited any great restaurants?

268. What is a piece of advice you often offer but find difficult to follow?

269. What is the most important aspect of friendship?

270. Would you rather live in squalor for a month with your best friend or in luxury for a year with someone you despise?

Relationship Questions

271. Do you ever bring your job home with you?

272. Do you think you would be the type of person to settle down, or is that something that doesn’t really appeal to you?

273. How would you react if someone made you your favorite food?

274. What has been the worst nickname you had when you were a kid?

275. What is that certain book that you’d love to see be made into a movie?

276. When was the last time you brag about something?

277. What is the most significant thing anyone has ever said to you?

278. How many times have you ever been in love?

279. Have you got something exciting planned for the rest of the weekend?

280. What is something you wish you had more time to do?

Intriguing Questions

281. What are some of the little things that brighten your day or make you smile?

282. Can you describe a personal indulgence for which you would never apologize?

283. What are your thoughts on a partner who consumes alcohol on a daily basis?

284. Which member of your family do you have the most in common with?

285. Do you like big parties or just small gatherings?

286. If you could invent a new ice cream flavor, what would it be?

287. What’s your wish for me?

288. What is something you would love to relive one day?

289. Do you enjoy debating controversial topics?

290. What subject was your favorite when you were in high school?

Common Questions

291. When do you feel like you’re the most out of place?

292. What’s your favorite verse in the Bible?

293. Are there any decent movies out right now that you want to see?

294. What is the first lesson you want to tell your children about love and relationships?

295. How do you feel about science vs. religion?

296. Have you been to Disney World before?

297. What is the priciest item you’ve ever purchased for yourself?

298. Have you ever considered starting your own business?

299. What are your top 5 favorite topics to talk about?

300. What is your most important goal right now?

Intriguing Questions

FAQs about First Date Questions

Below are frequently asked questions about first date questions

1. What are good questions for a first date?

▸ What do you like to do in your free time?

▸ Are you more of an indoors or outdoors person?

▸ Who is the most fascinating person you’ve met?

▸ What was the last book you really got into?

▸ What are some movies you really enjoyed?

▸ What amazing adventures have you been on?

▸ What pets have you had?


2. What are fun dating questions?

▸  “What Makes You Unique?”

▸ What are some random fun facts about you?”

▸  “What’s Something You Want to Learn or Wish You Were Better At?”

▸  “Would You Rather…?”

▸  “Know Any Good Jokes?”

▸  “What’s Your Favorite Place on Earth?”

▸  “Who Are the Special People in Your Life?”


3. What questions should you avoid on a first date?

▸ “You Seem Great, So Why Are You Still Single?”

▸ “What Dating Apps Are You On?”

▸ “You’re Not Crazy, Are You?”

▸ “Where Do You See This Relationship Going?”

▸ “How Much Did That Cost?”

▸ “Are You Seeing Anyone Else?”

▸ “Do You Like My Outfit?”

▸ “Do You Want to Have Kids?”


4. How do I go deep on a first date?

▸ Start by trying to make a connection.

▸ Build on what you already know.

▸ State the obvious.

▸ Pay attention to how they respond to you.

▸ Ask them about their talents.

▸ Learn about their family and friends.

▸ Unpack their idea of a “good life.”

▸ Address dealbreakers.


5. What are some flirty questions?

▸ What physical feature do you find most attractive in a guy?

▸ Do you believe in love at first sight?

▸ If I could take you out right now, where would you want to go?

▸ What are your biggest turn-ons?

▸ Do you believe in the idea of a soulmate?

▸ Who is your celebrity crush?


6. What are 10 questions to ask?

▸ Who is your hero?

▸ If you could live anywhere, where would it be?

▸ What is your biggest fear?

▸ What is your favorite family vacation?

▸ What would you change about yourself if you could?

▸ What really makes you angry?

▸ When is your birthday?

▸ What is your favorite animal?

▸ What do you do for a living?

▸ If you could travel anywhere in the world, where would you go?


7. What’s a deep question?

▸ If you could have one human talent that you don’t currently have, what would it be?

▸ If you had the power to correct one problem in the world, what would you fix?

▸ Where would you go if you could teleport anywhere in the world?

▸ If you could be an animal for a week, what would you be?


8. What’s a deep question to ask a guy?

▸ Do you consider yourself an introvert or an extrovert?

▸ What are you most thankful for?

▸ Which parent are you closer to and why?

▸ What are your thoughts on online dating or tinder?

▸ What’s on your bucket list this year?

▸ How would you describe your best friend?


9. Should we kiss on first date?

While you may have hit it off and have a lot in common, kissing on a first date enables you to see if you have any romantic rather than platonic potential.

If the kiss is as terrific as the date was, this can be a great indicator that you have matching styles.


10. How do you make a first date not awkward?

▸ Remind yourself that it is just a first date.

▸ Plan an activity date.

▸ Talk about topics you are passionate about.

▸ Listen with curiosity.

▸ Avoid potentially awkward topics and remember your date is still a stranger.

▸ Pump yourself up and remember to relax.


We believe this article on first date questions has been helpful as well as insightful. Please endeavor to share this article with family and friends.

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