Genuinely Interesting Questions For You To Ask Your Next Date
It’s really, REALLY attractive when people ask well thought out questions on a first date that at least give the illusion that they want to know you better—not just know where you went to college and what your worst OkCupid story is. Good questions like the below are sexy. So if you want to impress your next first date, memorize at least a few of them.
1. Who inspires you? Who do you aspire to be like?
2. What was the last book you read without skipping through anything?
3. What is the weirdest scar you have and how did you get it?
4. What is the most random thing you’ve ever watched all the way through on Netflix?
5. If you could trade lives with one person for an entire day who would it be and why?
6. Do you believe in ghosts?
7. Shark diving, bungee jumping, or sky diving?
8. Which would be harder for you to give up: coffee or alcohol?
9. How did you meet your best friend?
10. Do you have a sweet tooth or a savory tooth?
11. What is something you’ve always wanted to try but have been too scared to?
12. What accomplishments are you most proud of?
13. If you were going to go to the movies alone, what would be the perfect film for you to watch by yourself?
14. What is your favorite Wikipedia article? (Shuddup. Everyone has one.)
15. What is your favorite physical attribute about yourself?
16. Tell me about the best vacation you’ve ever taken.
17. Where is your favorite place to go on a weekday afternoon when you have no plans or obligations?
18. What is one of the weirdest things you used to do as a teenager?
19. Gin, vodka, or tequila?
20. What drives you to do what you do? What motivates you?
21. In your opinion, what is the best Disney movie to come out since Disney’s Golden Age?
22. What kind of phone was your first cell phone?
23. What did you love most about the place you grew up? What about it did you love the least?
24. What trajectory are you hoping to push yourself onto? Where do you want to head?
25. What is your most bizarre talent?
26. Is there a documentary or book that really changed the way you thought about something?
27. What are three albums (soundtracks or compilations don’t count) that really define you or have shaped you as a person?
28. Who was someone you really looked up to when you were little — someone you considered to be a mentor?
29. What’s your favorite cheesy pick-up line? Have you ever used it for real?
30. Who is a character from a TV show or a book that you’ve always resonated with?
31. Can I get you another drink?
32. Ask them to give you two “truths” and a lie. Then try to guess which one is a lie.
33. If you could write a note to your younger self, what would you say in only two words?
34. If you had to name one thing that really makes your day, what would it be?
35. What is a misconception others often have about you?
36. Whats the most valuable life lesson you have learned because of a mistake?
37. What’s an accomplishment you are really proud of?
38. Read anything interesting lately?
39. What’s one thing you wish you had known as a freshman in college?
40. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a fun way).
41. When it comes to love and relationships, what is the first lesson you want to teach your children?
42. If you could change one physical & non physical thing about yourself, what would it be?
43. What should I know about you that I’d never think to ask about?
44. What do you hate most about the dating process? (You want them to tell you so you can avoid it) ;)
45. What is #1 thing in your life that you are not doing that you wish you were?
46. What do you do when you feel like giving up?
47. If you could only keep one book you currently own, what would it be?
48. What are you most excited about in your life right now?
49. Describe one extravagance you have for which you will never apologize.
50. What do you want to be known for?
51. In one sentence what is your biggest concern right now?
52. Complete the following: There would be fewer divorces in this country if only people ________.
53. What’s something that you sometimes outwardly wish more people realized about you, but you’re happy is internalized because to be able to sit on this information makes you stronger?
54. How many times have you been in love & what did each experience teach you?
55. What’s something that comes easier to you than it does for most?
56. What do you feel people take for granted the most?
57. What are you better at than 90 percent of the population?
58.What is something about you that would surprise me?
59. What is a piece of advice you often give but find yourself struggling to follow?
60. Describe your perfect mate in one sentence.
61. When is the last time you did something courageous for yourself?
62. On a scale of one to ten, how happy are you? (Then sit silent and wait for their answer. The pause is important).
63. Whats the stupidest thing you’ve ever done for love?
64. What’s something many people fear that doesn’t scare you at all?
65. What’s something that instantly makes someone less attractive?
66. Would you describe yourself as more of an optimist, a pessimist, or a realist?
67. What would be a question you’d be afraid to tell the truth on?
68. What is something you wish you did more of in your life and something you wish you did less of?
69. Which significant other in your life has had the biggest impact on you and why?
70. What is a piece of advice that you were given that if you listened to it, you would not be where you are today?
71. If you had to spend a year alone with one other person who would it be and why?
72. What was the last thing you learned that made a big impact on you or an ah-ha moment?
73. If you only had 30 seconds to share one if the most important things you’ve learned with the world, what would it be?
74. What’s one fear you know is holding you back?
75. What was the last mistake you made that you’re sure you’ll probably make again?
76. When was the last time life left you breathless?
77. What are you really passionate about and why?
78. What’s the best advice someone has ever given you?
79. Where is your favorite travel get-away?
80. If you had one hour left to live what would you do?
81. What was your favorite year and why?
82. If you could meet someone who’s dead who would it be?
83. Do you have any tattoos? What do they mean?
84. If you could come back to life as an animal what animal would you be?
85. What’s one song you really relate to?
86. What was the last movie that made you cry? Or the last movie that made you emotional (for people who are too embarrassed to admit a movie made them cry)?
87. If you could be friends with a celebrity who would it be and why?
88. Have you ever laughed so hard you peed your pants? (Then ask what made them do it)
89. If I were to ask your friends about you what would they say?
90. What’s something you would never want your mother to know about you?
91. What is something you’ve never done that you’ve always wanted to do?
92. If you could live another life as someone else who would it be?
93. If you could change one thing about the world what would it be?
94. When was the last time you cried?
95. What do you think happens to us after we die?
96. What is your drink of choice?
97. What was your favorite game to play as a child?
98. Do you have any embarrassing nicknames you’d like to share? How’d you get them?
99. Dog or cat person?
100. What is one TV show you’re embarrassed to admit you watch?
101. What’s your favorite guilty pleasure food-wise?
102. What’s one book you’ve read that has caused some deep thinking?
103. What’s your most used emoji?
104. If you could pick an emoji to best describe you which one would it be?
105. What’s one character (could be from TV, a movie, or book) you identify with?
106. Have you ever broken a bone? How?
107. Coffee or tea?
108. If a high-school stereotype were to describe you in adulthood which one would it be?
109. Are you a morning or night person?
110. If you won the lottery, what’s the first thing you would buy?
111. What’s your favorite season?
112. Do you prefer hot or cold weather?
113. Would you rather live forever or die tomorrow?
114. What’s one lie you’ve told that you were caught in?
115. Who in your family are you closest to?
116. What would you say is your most redeeming quality?
117. What has been your biggest accomplishment in life so far?
Essential Get-To-Know You Questions You Can Rely On For Every First Date
First dates are nerve-wrecking. But they’re a whole lot less nerve-wrecking if you’re armed with the right questions to ask. These first date questions will help you get to know the person sitting across from you at the dinner table faster than usual.
118. What three U.S. cities would you never, ever move to even for the job offer of your dreams?
119. What combination of fixings makes your perfect burrito?
120. What is the best gift you’ve ever received?
121. What is the most thoughtful gift you’ve ever given?
122. Who is your role model or has had the biggest influence on your life?
123. Do you have any nicknames?
124. What’s one thing you wish you had known as a freshman in college?
125. How many siblings do you have?
126. Do you consider yourself a morning person or a night owl?
127. How long did it take you to start enjoying coffee?
128. What do your parents do for a living?
129. What quality is your automatic “no fucking way” when pursuing a potential relationship?
130. What are two of your bucket list items?
131. Have you ever kept a New Year’s resolution?
132. Were you closer with your mom or your dad growing up?
133. What is something you are financially saving up for currently?
134. Where is your happy space?
135. What is your favorite article of clothing you own?
136. Do you have any specialty cooking dishes?
137. What is one job you could never do?
138. When is your birthday?
139. What is in your fridge right now?
140. What are you worse at than 90 percent of the population?
141. Do you believe in aliens?
142. Do you think it’s the little things or grand gestures that count the most?
143. Have you ever been out of the country?
144. What fact about you surprises people the most?
145. What do you do for a living?
146. What’s the most spontaneous thing you’ve ever done?
147. What’s your ideal vacation?
149. If you could live in any other U.S. city, which city would you live in?
150. What was your favorite family vacation growing up?
151. Are you a big fan of any major pro sports team?
152. What was your favorite subject in school?
153. What are you better at than 90 percent of the population?
154. If you could travel back to any one point in time what would it be?
155. What is the proudest moment or greatest achievement of your life so far?
156. How did you meet your best friend?
157. If you could be any animal, what would you be?
158. Salty snacks or desserts?
159. What is a family tradition your family has?
160. What do you think is the most important life lesson for someone to learn?
161. What was your favorite toy growing up?
162. Who was your favorite teacher or professor?
163. What is the best advice you’ve received?
164. What’s the luckiest thing that’s ever happened to you?
165. What do you feel people take for granted the most?
166. What do you like the most about (insert city of residence)?
167. What is the craziest scene or event you have ever witnessed?
168. What is your biggest pet peeve?
169. What was the worst job you’ve ever had?
170. What was the last book you read?
171. When you were younger, what did you want to be when you grew up?
172. What was something that recently moved you?
173. What skill or talent do you wish you had or were better at?
174. If you just won $1 million, what would you do with it?
175. If you could have a superpower what would you want it to be?
176. What are you passionate about?
177. What is your favorite movie?
178. Are you a cat person, a dog person, both or neither?
179. What do you think is your greatest strength?
180. If you had to be a vegetable, which vegetable would you least like to be?
Fun Questions To Ask On A First Date To Start (And Keep) A Good Conversation Going
Conversations tend to lull every so often, especially with people you don’t know all that well. When you’re on a first date, it’s a good idea to ask lots of questions so you can kickstart a good conversation and / or keep it going.
181. If you could invite five people, dead or alive, to a dinner party, who would you choose and why?
182. When you were little, where did you think you’d be by now? Are you there?
183. What was the last dream you had?
184. If you could start a band, what kind would it be and would you name it?
185. Were Ross and Rachel on a break?
186. What was the first album you bought, and why did you buy it?
187. It’s your 75th birthday. Where do you see yourself?
188. What is your favorite mistake?
189. Who do you look up to of the same sex?
190. Who is your role model of the opposite sex?
191. It’s New York City in the 1920’s. What are you doing?
192. What is your favorite book?
193. What is your guilty pleasure song?
194. What was a situation that you initially thought was terrible, but ended up being a blessing in disguise?
195. What’s your favorite word?
196. If you could choose a decade to grow up in, which would you choose?
197. What was your first concert?
198. The stupidest thing you’ve ever spent money on?
199. What would your superpower be?
200. And your superhero name?
201. If you could live in any city, which would you choose? Why?
202. Could you spend a day without your phone?
203. What about a week?
204. The Rolling Stones or the Beatles?
205. If you could be a type of beer, which would you be? Why?
206. If you could live in any fantasy world, be it Hogwarts or Narnia, where would you choose? Why?
207. What is the last book you read? Did you like it?
208. If you could have any talent, which would you have?
209. What was your AIM screenname? Why did you choose it?
210. Would you like to go out again next week?
211. If you were stranded on an island, what is one item you would take with you?
212. Who is your favorite band or musician?
213. Are you more of a morning person or night owl?
214. Where would you go on your dream vacation?
215. Who is the closest person to you and why?
216. Who inspires you?
217. What is your favorite childhood memory?
218. What kind of hobbies do you enjoy?
219. Do you have any fears? If so, what are they?
220. What are your current goals in life?
221. Do have a favorite color and why?
222. What would you choose as your top meal?
223. What is your favorite city you have been to?
224. What is on your bucket list?
225. If you had no fears, what would be the first thing you would do?
226. Do you have siblings?
227. Where did you grow up at?
228. What do value in others?
229. What is your favorite book you have read?
230. What is one piece advice you would give to someone?
231. If you didn’t have to work, what would you do for a living?
232. What is your favorite cuisine to cook?
233. Do you have any vices?
234. What’s one thing you cannot live without?
235. Do you speak any other languages?
236. What is your favorite movie?
237. If you had to describe yourself in three words, what would they be?
238. What is your astrology sign?
239. Do you have any awkward family traditions?
240. If you were an animal, what would you be and why?
241. Do you have any pets?
242. Are you an introvert, extrovert, or ambivert?
243. How long have you lived here?
244. Have you ever lived in another country?
245. Are you more of an indoors or outdoors person?
246. What is your favorite athletic activity?
247. What are you known for amongst your friends?
248. How do you unwind?
249. What are you most grateful for?
250. What is your favorite holiday? How do you celebrate it?
251. What is the most interesting fact about you?
252. If you were to go on a road trip, where would you go?
253. Who has impacted you the most in life?
254. What is one thing you still want to learn?
255. What is your favorite way to spend your time off?
256. What brings you happiness in life?
257. Do you have any pet peeves?
258. If you were to be notable for something what would it be?
259. What’s one thing you practice on a daily basis that improves your life?
260. What is the longest timespan you could live without your phone?
Deep First Date Questions That’ll Put Your Chemistry To The Test Right Away
If you’re one of those people who would rather skip the small talk and get right to the chase, these are the first date questions to ask. If you get through enough of these first date questions, you’ll have a much better sense as to whether or not the relationship will happen, and whether it’ll last.
261. What do you hate the most about modern dating?
262. Has a book ever changed your life?
263. Do you believe in love at first sight or do you think it’s bullshit?
264. If aliens came to Earth, would you be scared of them or would you welcome them?
265. Has a song ever made you cry?
266. Why do you get up in the morning?
267. What’s the most inspirational saying you’ve ever heard?
268. What’s the worst thing that you’ve ever done?
269. If you could rewind time, what one moment would you want to relive?
270. If you were famous, would you still want a relationship or would you sleep around?
271. If you were free to murder one person without getting punished, would you?
272. Do you think people are born good or born evil?
273. Have you ever had a near-death experience?
274. Would you rather be hideous or illiterate?
275. Have you ever had your heart broken?
276. What’s the sweetest gift you’ve ever given your mother?
277. What was the first thing you masturbated to?
278. Are you proud to tell people about your job or embarrassed about what you do?
279. Do you think an animal’s life is just as valuable as a human’s life?
280. Has a celebrity’s death ever caused you to cry?
281. Do you resent your exes or do you wish them well?
282. If you got a girl pregnant, would you consider it a burden or a blessing?
283. Do you like what you see when you look in the mirror?
284. Have you ever written poetry? What about song lyrics?
285. Who would you call if you only had moments left to live?
286. Do you believe in magic?
287. Do you believe in the afterlife?
288. Do you usually go with your gut or with your brain?
289. What celebrity do you think deserves more attention?
290. Have you ever questioned your sexuality?
291. Is there anyone in this world that you genuinly hate?
292. Would the childhood version of you look up to the current version of you?
293. How are you going to leave your mark on the world?
294. Would you lie to keep your best friend out of prison?
295. What type of imaginary scenarios do you create in your head?
296. What’s the earliest memory you have of life?
297. What’s the most important thing on your bucket list?
298. Do you consider yourself to be a good person?
299. Do you think you have a purpose in life?
300. Do you think you’d be capable of murder?
301. Do you believe men and women can “just” be friends?
302. Are you following your dreams or have you given up on them?
303. Which gender stereotype about men do you hate the most?
304. If you could erase specific memories from your mind, would you?
305. Do you love your pets as much as you love your human family members?
306. Have you ever seen a ghost? If not, do you believe they exist?
307. Which fictional character do you relate the most to?
308. Would you choose to live forever if you had the opportunity?
309. Who was your hero when you were a little kid?
310. How do you feel about me?
311. Is it obvious that I’ve dressed up for this special occasion?
312. Have you tried to Google me?
313. Will you believe me if I say I didn’t totally check your social media accounts on my way here?
314. Does anyone know you’re on a date right now?
315. How long have you prepared for this date?
316. Do you easily get bored?
317. Can we try not to touch our phones for half an hour?
318. What’s your first impression of me?
319. What do you like about me so far?
320. Do you feel things deeply? Immensely? Greatly?
321. Have you tried suppressing your emotions? Has it worked?
322. Are you okay talking about feelings?
323. What are your thoughts about someone who’s a chronic over-sharer? Just curious.
324. Do you stare at your ceiling before you sleep?
325. Which has a higher spot in your priority — relationship or career?
326. Are you one of those people who consider dates as job interviews?
327. Okay…so how many dates have you been on before this?
328. How many hearts did you break in the past?
329. What’s your point of view about the idea of forever?
330. When is the right age for you to settle down?
331. What would you do if I just start crying and screaming right now?
332. Do you believe in astrology? When’s your birthday?
333. If I tell you our zodiac signs are super compatible, will you agree on a second date?
334. Have you ghosted someone before?
335. Who has been the biggest influence on your life?
336. What’s your favorite place in the entire world?
337. What really makes you laugh?
338. What’s your favorite movie of all time?
339. What’s your favorite book of all time?
340. What’s your biggest goal right now?
341. What’s your favorite way to spend a weekend?
342. What should I know about you that I would never think to ask about?
343. Have you traveled anywhere really cool lately?
344. Is there anywhere else you would love to live, other than here?
345. What’s on your bucket list?
346. What’s your favorite thing about your job?
347. What is the most thoughtful gift you’ve ever received?
348. What do you feel most passionate about?
349. What’s something you’ve been really proud of lately?
350. What’s something you’ve always wanted to try?
351. What’s one of your favorite childhood memories?
352. What is your favorite thing to cook?
353. What’s your favorite piece of clothing that you own?
354. What is your absolute dream job?
355. Do you consider yourself spontaneous, or a planner?
356. What quality for you is an automatic “no way” when pursuing someone in a relationship?
357. How would your best friends describe you?
358. What is the best single piece of advice you’ve ever received?
359. What is a tradition your family had when you were a kid?
360. What was the worst job you’ve ever had?
361. When you were a kid, what did you hope to do when you grew up?
362. What is one skill you wish you could be better at?
363. If you could donate to any charity, which charity would it be and why?
364. In one word, how would you describe yourself?
365. What do you find most attractive in a potential partner?
366. If you were stuck on a deserted island, who would you choose to have with you?
367. For what in your life do you feel most grateful?
Somewhat Whacky But Absolutely Vital Questions You Must Ask On A First Date
If you’re kind of a weirdo and you want your date to know it, these are the first date questions that will help you let your freak flag fly.
368. How many times a day do you try and use The Force?
369. Gun to your head, must choose one: garlic bread or cinnamon rolls?
370. What’s your opinion on sweatpants?
371. Do you cheat when playing Monopoly most of the time or all of the time?
372. Bulbasaur, Squirtle, or Charmander?
373. You spot a terrifying-looking spider a foot away from you. How do you react?
374. On a scale of 1-10, how much do you drench your pancakes in syrup? (1 being “a lot” and 10 being “Syrup with a side of pancakes.”)
375. On average, how long does it take you to cry yourself to sleep every night?
376. Orange Is The New Black or House of Cards?
377. On average, how many hashtags do you include on an Instagram photo?
378. Who’s your favorite Game of Thrones character? Tyrion or Tyrion?
379. What’s the longest amount of time you’ve spent binge watching something?
380. Who are your favorite celebrity twins and how many days has it been since you last watched Passport to Paris?
381. At what point in the afternoon do you change out of your pajamas?
382. How many sauce packets do you ask for with an order of chicken nuggets?
383. Was Leo still in a dream at the end of Inception?
384. Would you say that Cloris Leachman is basically Betty White’s rebellious cousin?
385. Which Disney villain would you play tetherball with?
386. When a friend pulls you onstage for karaoke, how many lines do you sing before you stab yourself with a stirring stick?
387. What’s the last funny prank you pulled on a friend or family member?
388. What’s the weirdest thing someone’s caught you doing?
389. Where would you go if the zombie apocalypse happened right this second?
390. Was there enough room for Jack on that floating door that saved Rose?
391. Were Ross and Rachel on a break?
392. What’s your favorite thing to do when no one’s looking?
393. What’s your most irrational fear?
394. What’s your mom’s favorite memory of you as a kid?
395. What’s the most embarrassing thing that’s ever happened to you?
396. What’s the greatest trick that’s ever been played on you?
397. What superlative would you award each of your parents and why?
398. What’s your favorite way to eat ice cream?
399. What food can you just not resist?
400. What cartoon character do you most identify with?
401. If you were a carbonated beverage, which one would you be?