351 Juicy Questions to Ask Your Friends, From Funny to Deep

People love to talk about themselves. Studies show that talking about oneself^{1https://www.pnas.org/doi/abs/10.1073/pnas.1202129109} activates the same parts of your brain as food, drugs, and sex! 

Self-disclosure (and getting other people to open up) is scientifically proven to make you more likable^{2https://labs.psych.ucsb.edu/collins/nancy/UCSB_Close_Relationships_Lab/Publications_files/Collins%20and%20Miller,%201994.pdf} and help you form deeper social bonds^{3http://books.google.com/books/about/Grooming_Gossip_and_the_Evolution_of_Lan.html?id=nN5DFNT-6ToC}.

Want to start a conversation with anyone? Watch our video to learn these killer conversation starters:

Here are 331 juicy and thought-provoking conversation starters to get to know someone better and (hopefully) create an intriguing and memorable conversation. 

Random Questions to Ask Your Friends About Their Interests

When you’re trying to bridge the gap between small talk and deep conversation, the most accessible place to start is asking about what someone likes. 

1. What’s the best birthday party you’ve ever had?
2. Where is your favorite place you’ve ever visited?
3. How do you like to spend your free time? 
4. What’s one of your favorite bands?
5. What is the cutest animal you’ve ever seen in person?
6. How would you describe your style?
7. If your wardrobe could only be one color, what would it be? 
8. What was the first concert you ever went to?
9. What is the best book you’ve ever read?
10. What’s your favorite movie of all time? 
11. What’s the stupidest movie or TV show you’ve ever seen?
12. If you could only have one food for the rest of your life, what would you choose?
13. What are your biggest pet peeves?
14. Are you more into brains or looks?
15. Do you celebrate any holidays? What’s your favorite?
16. What’s your guilty pleasure? 
17. Which meal is your favorite: breakfast, lunch, or dinner?
18. What do you do when you want to chill out after a long day?
19. How would you spend your ideal weekend?
20. Do you listen to podcasts, or mostly just music? What’s your favorite podcast?
21. Do you prefer to go to the movies or watch movies at home?
22. What was your favorite TV show growing up?
23. What’s your favorite TV show now?
24. How would you spend your birthday if money was no object? 
25. What’s your favorite season? What do you love most about it?
26. Do you prefer camping or going to the beach? 
27. Which phone app do you think you use the most?
28. Would you instead cook, order delivery, or go out to eat? 
29. How do you drink your coffee?
30. If you could have any animal as a pet, what would you choose? 
31. Do you enjoy being alone? How do you spend your alone time?  
32. What is your biggest pet peeve?
33. Are you more of an extrovert or introvert? 
34. How would your closest friends describe you? 
35. When you’re in a bad mood, is there something or someone that can instantly make it better? Who or what?
36. What is the best gift you’ve ever received? 
37. What is your favorite part of your daily routine? 

Yes or No Questions to Ask Your Friends

For a quick introduction to someone, yes/no questions are low-pressure and leave room for elaboration. These are also quick-fire ways to get to know someone quickly. 

Want to have fun? Answer at the same time and see if your answers match!

38. Have you ever kept a journal? 
39. Do you have a best friend?
40. Do you pay attention to the news?
41. Have you ever gotten a speeding ticket? 
42. Do you live alone?
43. Do you have any kids?
44. Do you like your job?
45. Did you ever go to college?
46. Have you ever been on TV?
47. Do you believe in ghosts?
48. Do you like cilantro? 
49. Do you ever talk to yourself in your head?
50. Do you sing in the shower?
51. Have you ever had deja vu? 
52. Do you believe in aliens?
53.  Do you like chocolate?
54. Do you own bitcoin? 

Questions to Ask Friends About Their Job

Asking friends about their job doesn’t have to be super bland. There is a lot more to a career than meets the eye. Use these questions to understand more about a friend’s interests, motivations, and goals in the professional realm. 

However, if someone clarifies that they don’t enjoy their job (for example, they give concise answers or make negative comments), you may want to move on to a different topic of conversation or only focus on questions related to their dream job or future aspirations. 

55. What do you enjoy most about your career?
56. What was your greatest accomplishment in the past year?
57. What motivates you to work hard at what you do? 
58. How long have you been doing this job? 
59. What was your first job? Did you enjoy it?
60. How do you define success?
61. What’s your least favorite thing about your job? 
62. Have you ever had “imposter syndrome”? What did you do about it? 
63. Would you instead make a lot of money at a job you hate or make less money doing something you love? 
64. Are there any exciting projects you’re currently working on?
65. Do you prefer working remotely or in an office?
66. What career did your parents try to get you to pursue?
67. Is your career path the same as your college degree?
68. What does the average week look like for you?
69. Do you prefer a time-block schedule or a simple to-do list?
70. What are your career aspirations?
71. What is one job you’ve always wanted to try?
72. Do you think your personality matches your current job?
73. What was the worst interview you ever had?
74. Where do you see yourself professionally in the next 5 or 10 years?
75. When you were a kid, how did you answer the question, “what do you want to be when you grow up?”
76. Did you ever expect yourself to end up in the job you have now?
77. Do you consider your job fulfilling? Why or why not?
78. Do you think it’s possible to have your passion and job be the same thing?
79. What is the wisest business advice someone has ever given you?
80. Who do you admire most in your professional circle?
81. Who was the most influential mentor in your career so far? 

Questions to Ask Your Friends About Yourself

See how well your friends know you with fun questions about yourself and their perception of you.

82. How would you describe me in 3 words?
83. What was the first thing you thought of me when we met?
84. What’s the most annoying trait I have?
85. Where do you see me in five years?
86. What attracts you to people? 
87. What is my favorite food?
88. What job do you think I would be perfect for? 
89. Where can you always find me?
90. What is the most fun memory we’ve had during our friendship? 
91. Do you know my middle name?
92. Do you know about my birthday?
93. What’s my favorite color? 
94. If I called you in the middle of the night, would you pick me up?

Questions About Childhood Memories

By inquiring about a friend’s early years, you get a unique window into the special moments that shaped who they are today.

From mischievous escapades to innocent wonders, these questions are designed to unearth those hidden gems and provide a deeper understanding of one’s roots.

95. What’s your earliest memory from childhood?
96. Did you have a favorite toy or comfort object growing up? What was it?
97. Can you recall a childhood game or pastime that you could play for hours?
98. Were there any family traditions that you looked forward to every year?
99. Do you remember any bedtime stories or lullabies that were special to you?
100. What’s a typical summer day like for you as a child?
101. Were you ever involved in any mischievous pranks or adventures? Do share!
102. Is there a childhood friend that you’re still in touch with today? How has your relationship evolved?
103. What was the best birthday gift you ever received as a kid?
104. Can you remember a time when you got into trouble, and what was it for?
105. Did you have a favorite place to hide or a secret spot you’d retreat to?
106. How would you describe your childhood self in three words?
107. Were there any TV shows, movies, or books from your childhood that left a lasting impression?
108. Did you ever have a childhood pet? What were they like?
109. Are there any lessons or values from your childhood that you still carry with you today?

Questions to Ask Friends About Hobbies

How someone spends their leisure time is an essential clue as to what kind of person they are. Asking a passionate person about their hobbies can get them talking. 

These questions are broad openers that you should follow up with more topic-specific questions if someone has a particular hobby that they are excited about. 

110. What are you passionate about outside of work?
111. If you had unlimited free time, how would you spend it?
112. Do you have any hobbies?
113. What do you do for fun? 
114. How did you get into your hobby? 
115. What lights you up about your hobbies?
116. Do you collect anything?
117. What’s your favorite sport?
118. Have you ever been in a sports league? 
119. Do you think hobbies are important? 
120. Would you consider yourself a creative person?
121. Have you ever tried a creative endeavor like painting, writing, or acting?
122. Do you like to sing or dance?
123. What hobbies did you try as a kid? Which ones did you love and which did you despise?
124. What is your idea of a perfect vacation?
125. What’s your favorite type of workout or exercise? 
126. What is your favorite thing to learn about?

Questions About Travel and Adventure Experiences

Diving into a friend’s travel and adventure experiences can be a thrilling way to vicariously explore the world. Not only does it provide a glimpse into different cultures and terrains they’ve witnessed, but it also reveals how they adapt, discover, and grow in unfamiliar territories.

So, whether you’re speaking with a globe-trotter or someone who loves discovering local hideouts, these questions will surely spark a lively conversation.

127. What’s the most exotic place you’ve ever visited?
128. Have you ever traveled solo? If so, what was the experience like?
129. What’s the most adventurous thing you’ve done while traveling?
130. Is there a destination you’ve been to that you’d never go back to? Why?
131. Which place is at the top of your bucket list and why?
132. Have you ever faced a challenging situation or culture shock in a foreign land? How did you handle it?
133. What’s the most unforgettable meal you’ve had while traveling?
134. Can you share a heartwarming story you experienced during your travels?
135. Are there any travel experiences that changed your perspective on life?
136. What’s your preferred travel style: luxury resorts, backpacking, or something in-between?
137. Which historical or world heritage site left a profound impact on you?
138. How do you deal with language barriers when traveling?
139. Is there a local custom or tradition from somewhere you’ve visited that you wish was practiced everywhere?
140. Have you ever participated in an adrenaline-pumping activity like skydiving, bungee jumping, or deep-sea diving during your travels?
141. What are the top three things you always pack, no matter where you’re going?

Funny Questions and Weird Questions to Ask Your Friends

Research shows that shared laughter brings people together^{4https://www.springerprofessional.de/en/when-sharing-a-laugh-means-sharing-more-testing-the-role-of-shar/11733488}. If you’re looking for some lighthearted conversation or opportunities for witty banter, these questions let you explore your goofy side. 

142. Have you ever waved at someone, thinking you know them, only to realize they are the wrong person? 
143. Do you eat or drink soup?
144. What is a song you pretend you don’t like because it’s embarrassing to enjoy it? 
145. Have you ever tried to look cool in front of someone and failed?
146. What’s the strangest thing you’ve seen someone do in public? 
147. When was the last time you had a big fail moment? 
148. If you could live anywhere in the world but had to stay naked all the time, where would you choose?  
149. What voice accent impersonations can you do (British, Australian, country, etc.)? 
150. What’s your favorite corny joke?
151. Have you ever tripped or fallen in front of a vast crowd?
152. What is the weirdest fact you know?
153. What is the strangest joke someone has asked you? 
154. If you could have one useless superpower, what would it be?
155. Which sport would be funniest if it had mandatory alcohol?
156. If animals could talk, which would be the most sarcastic?
157. What is one thing that people consider trashy but you consider classy?
158. What’s the most awkward first date you’ve ever been on? 
159. What’s your favorite white elephant gift?
160. Where is the worst smelling place you’ve ever been? 
161. What is the most fruitless talent you have? 
162. If you got banned from the library, what would be the reason behind it?
163. Do you think penguins have knees?
164. Why is it called lipstick if it doesn’t stick your lips together?
165. What’s the silliest way you’ve accidentally injured yourself?
166. What would be the worst bio for a dating app? 

Questions About Family

Family relationships and upbringing have a significant impact on who people become as adults. Showing interest in someone’s family demonstrates that you want to get closer to them and understand their origins.   

167. Who is your closest family member?
168. Do you have a best friend that you talk to daily?
169. What kind of relationship do you have with your parents? 
170. How much time do you usually spend with your family?
171. Who in your family do you most enjoy being around, and why?
172. Which family member cooks the best food?
173. What’s the most challenging part about spending time away from your family?
174. Do you have any siblings? Tell me about them?
175. Are you close with your brother(s)/sister(s)? What drives you crazy about them?
176. Do you ever wish you had more or fewer siblings?
177. Who gives the best gifts in your family?
178. Which holiday did you celebrate most with your family when growing up?
179. What’s your favorite story your grandparents have told you?
180. Have you ever looked into your family lineage? Do you know anything about your ancestry?
181. What is your favorite memory with your family?
182. What is the best piece of advice your grandparents or parents have ever given you?
183. Were you a rebel or an obedient kid growing up? Did you hide things from your parents?
184. How would you describe your family now?
185. Does anyone in your family have a nickname for you?
186. What’s your favorite tradition in your family?
187. What will always bring your family together?
188. Is anyone in your family a “character”? What makes them so unique?
189. Who is the “black sheep” of your family?
190. Do you think friends or family are more important?
191. How do you deal with arguments in your family?
192. What’s something your family doesn’t know about you?
193. Do you look more like your mom or dad?
194. Do you know how your parents met?
195. What was your favorite story your family members told you as a kid?
196. What was the most challenging part about growing up in your family?
197. What are you most grateful for about your family?
198. Who in your family makes you feel the safest?
199. Is there a particular food your family always makes when they get together?
200. What kind of music does your family listen to? 
201. What was the house like that you grew up in? 

Health and Wellness Questions

Whether it’s about physical fitness, mental health, or nutritional choices, these conversations can be enlightening, motivating, and at times, deeply personal. Approach these topics with sensitivity and an open heart, as they can sometimes touch on intimate struggles and achievements.

202. How do you usually start your day for a positive and energetic kickstart?
203. Do you follow any specific dietary choices or restrictions? What motivated that decision?
204. What’s your favorite form of physical exercise, and why do you love it?
205. How do you prioritize mental well-being in your daily routine?
206. Are there any wellness books, podcasts, or influencers that have made a significant impact on your health journey?
207. How do you handle stress or anxiety when it creeps into your life?
208. Do you practice meditation or any form of mindfulness exercise?
209. What’s your go-to comfort food when you need a little pick-me-up?
210. Are there any particular health challenges you’ve faced and conquered?
211. How do you balance work-life and ensure you get adequate relaxation?
212. Do you use any apps or gadgets to monitor or enhance your wellness journey?
213. What are your thoughts on alternative therapies like acupuncture, chiropractic care, or herbal medicine?
214. How do you ensure quality sleep and maintain a regular sleep pattern?
215. What are your views on supplements and vitamins? Do you take any regularly?
216. Do you have a personal mantra or philosophy that guides your wellness decisions?

Questions About Values and Goals

Finding out someone’s morals and values is more complex than simply asking, “what are your values?” You can get to the root of what someone believes in by asking things about their motivations, life philosophies, and what drives them forward daily. 

It is also helpful to ask some thought-provoking questions about hypothetical scenarios like “If you could time travel, what time period would you go to?” This allows them to talk about their values in a hypothetical situation without feeling pressured to reveal more profound stories if they don’t want to.

217. How do you hope people feel when they’re around you?
218. What are the most important values that you have always stood by?
219. How would you define a “good person”? 
220. What are the most essential qualities you want in a friend?
221. What life lessons did you have to learn the hard way?
222. If you only had one of your five senses, which one would you choose?
223. Have you ever volunteered?
224. What are causes important to you? 
225. Who do you admire the most and why?
226. What is your life motto or mantra?
227. What was your most proud accomplishment in the past year?
228. If you could choose one thing that would make the world better, what would it be?
229. Do you believe in astrology? Why or why not?
230. What is your astrological sign?
231. Do you believe in giving people second chances?
232. How can someone earn your trust?
233. What has someone done to lose your trust?
234. Do you believe in aliens or life on other planets?
235. What do you think about manifestation? Have you ever tried it? 
236. Do you have vivid dreams? 
237. Do you think dreams have a deeper meaning?
238. Where have you always dreamed of going?
239. Do you believe you should do one thing every day that scares you?
240. What does getting out of your comfort zone look like for you?
241. How do you define beauty in a person or life?
242. What is a boundary you have that you’ve always upheld?
243. What boundary do you have a more challenging time reinforcing?
244. What do you think holds people back the most from achieving their goals and dreams?
245. When you want to give up on something, what keeps you moving forward?
246. When was the last time you had a regret?
247. Do you live by any particular words of wisdom?
248. Is it easy or difficult for you to accept help from people?
249. If money were no object, what would you devote your life to? 
250. Have you ever wanted to start a business? What kind would it be and why?
251. If you could live forever, would you want to? Why?
252. If you could time travel, what period would you go to?
253. If you could go back in history and spend a day with one famous person, would it be?
254. Do you have a vision board? If so, what is currently on it?
255. A genie in a bottle randomly gives you three wishes– what are they?
256. If you could live anywhere in the world, where would you choose? Why?
257. If you found out today was your last day on Earth, how would you spend it?
258. If you find yourself stranded on a deserted island, what three things would you want to have with you? 
259. What is your number one goal for the coming year?

Pro Tip: There is a certain balance you have to strike between expressing interest in someone versus being too nosey. You don’t want to violate their privacy or go too deep too quickly. 

It’s usually best to steer clear of certain types of questions early on in a friendship: for example, “who did you vote for?”, “what are your religious beliefs?” or “what’s the worst thing that ever happened to you?” are probably best saved for someone you’ve known for a while. 

On the other hand, if you notice someone is sharing more about themselves, move on to more profound questions like the ones below.

Juicy Questions About Romance and Relationships

Finding out about someone’s perspectives and experiences with relationships is a powerful way to get a little closer to their heart. But there is a time and place for everything. 

It’s best to avoid asking these questions to professional colleagues, new acquaintances, or on a first date. Instead, dive into the relationship realm with friends and significant others that you’ve known for a little while. 

260. Have you ever been in love?
261. What is the most attractive quality in a man/woman?
262. Do you’re a good kisser? 
263. What is your idea of a perfect date? 
264. Do you believe in love at first sight? 
265. What was it like the first time you met your significant other? (if they have one) 
266. Do you think people fall in love because the right person shows up or because the time in their life is right? 
267. What did your past relationship teach you?
268. Do you believe in soul mates? Why or why not?
269. Would you ever take somebody back who cheated on you? 
270. Would you uproot and relocate your life for someone you love? 
271. What is a relationship deal-breaker for you?
272. Do you ever want to have a family of your own someday?
273. Have you heard of love languages? What is your love language?
274. What is your favorite book or romantic movie?
275. What is the sweetest thing anyone has ever done for you?
276. Which is more romantic: flowers and gifts or a candlelit meal?
277. Do you think that people meet for a reason or by chance?
278. What’s the best advice an older person has ever given you about relationships?
279. How do you get over heartbreak?
280. How old were you when you had your first boyfriend/girlfriend?
281. What are your top 3 most essential qualities in a romantic partner?
282. What is the longest relationship you’ve been in? 

Questions About Their Pet Peeves and Annoyances

Everyone has those little things that just get under their skin, from seemingly insignificant habits to particular behaviors. Ready to dive into the quirky frustrations of daily life? Let’s explore with these questions.

283. What’s one common behavior that you find inexplicably irritating?
284. Do you have any specific sounds that just make you cringe? (like nails on a chalkboard)
285. How do you feel about people who consistently show up late?
286. Are there any words or phrases that people commonly misuse that bother you?
287. What’s your biggest dining-out or restaurant-related pet peeve?
288. How do you handle someone who constantly interrupts you while you’re speaking?
289. Are there any particular tech or social media habits that you find bothersome?
290. How do you feel about people who overuse emojis or text speak (like “lol”, “brb”) in professional settings?
291. Is there a trend or fad that you just couldn’t understand or get behind?
292. What’s one hygiene-related pet peeve you wish more people were aware of?
293. How do you deal with drivers who don’t signal or practice courteous driving?
294. Do you get irked by certain email habits, like excessive CC-ing or vague subject lines?
295. How do you feel about spoilers or people who reveal plot twists without warning?
296. Are there any fashion trends or styles that you just can’t stand?
297. What’s the one household chore or habit that you wish everyone would do (or not do) consistently?

Cultural Questions to Ask Your Friends

Engaging in conversations about cultural experiences can be an enlightening journey, helping to break down barriers and foster mutual respect. When exploring these topics, approach them with genuine curiosity and an eagerness to learn.

298. Which culture, other than your own, do you feel most drawn to and why?
299. Have you ever attended a cultural festival or celebration that left a lasting impression on you?
300. Can you describe a dish from another culture that you tried and absolutely loved?
301. Is there a particular cultural tradition or ritual you’ve adopted into your own life?
302. Have you ever experienced culture shock? What was it like, and how did you adapt?
303. Are there any global customs or etiquettes that you found fascinating or unique?
304. How do you approach and respect cultural sensitivities when you travel?
305. Can you share a memorable story or experience related to a traditional dance or music performance you’ve witnessed?
306. What’s the most meaningful souvenir or artifact you’ve brought back from your travels?
307. How has engaging with different cultures impacted or changed your worldview?
308. Do you speak any other languages? How has that helped in understanding another culture better?
309. Have you ever participated in a cultural exchange program or stayed with a host family abroad?
310. What’s a cultural myth or misconception you once held and later realized was incorrect?
311. Are there any cultural histories or legends that resonate deeply with you?

Deep Questions to Ask Your Friends

When you want to get to know someone deeper, it is often helpful to open up about your own stories and viewpoints.

Psychologists have found that an equal amount of give-and-take^{5https://doi.org/10.1016/j.jesp.2013.03.017} is essential to make both people in a conversation feel comfortable to disclose more intimate details about their lives.

However, over-sharing can lead to^{6https://research.vu.nl/en/publications/situational-privacy-and-self-disclosure-communication-processes-i} awkwardness or embarrassment. Self-disclosure requires trust that you can only build through time and conversation. So only dig into these types of questions once you’ve already started to form a relationship with somebody.

312. How would you title this chapter of your life? 
313. If you only had one month left to live, how would you spend it? 
314. What is the best advice someone has ever given you? 
315. What makes you feel alive?
316. Do you typically follow your heart or your head?
317. What are you most grateful for in your life? 
318. If you could go back and change one thing about your past, what would it be? 
319. Which is more critical – beauty, power, or money? 
320. What’s your biggest fear?
321. What makes you feel unstoppable?
322. What is your biggest regret?
323. Do you think people are mostly good or mostly evil? Why? 
324. Where do you go when you need fresh inspiration?
325. What’s your philosophy on life?
326. Do you like diving into the deep end or easing your way into the water? (literally or figuratively)?
327. What life-changing events have you experienced? 
328. What’s one thing you would change about yourself? 
329. Have you ever had a moment of deja vu? 
330. What legacy do you want to leave on Earth once you’re gone? 
331. What gives you hope? 

Questions to Ask Friends About Learning and Personal Growth

Exploring the realm of learning and personal growth with your friends can provide deep insights into their aspirations, challenges, and perspectives on self-improvement. These questions are designed to delve into their past experiences, current endeavors, and future goals, offering a comprehensive view of their journey towards personal development.

332. What new skill have you always wanted to learn but haven’t yet? Why?
333. Can you share a time when you stepped out of your comfort zone? What did you learn from that experience?
334. How do you approach setting and achieving your personal and professional goals?
335. Who has been your biggest inspiration in your journey of personal growth, and why?
336. What book, podcast, or resource has significantly impacted your outlook on personal development?
337. How do you deal with failure or setbacks? Can you share an example?
338. In what ways do you actively seek feedback to improve yourself, and how do you apply it?
339. What habits have you developed that positively contribute to your personal growth?
340. How do you maintain motivation and momentum in your personal development journey?
341. What’s the most challenging aspect of personal growth for you, and how do you manage it?
342. Can you share an achievement you’re particularly proud of in your personal growth journey?
343. How has your approach to learning and personal development changed over the years?
344. What role does mindfulness or reflection play in your personal growth?
345. Do you have a mentor or coach? How have they influenced your development?
346. How do you prioritize your mental and emotional health in your personal growth plans?
347. What’s one piece of advice you’d give to someone starting their personal growth journey?
348. How do you balance the pursuit of personal growth with other responsibilities and interests?
349. Can you describe a pivotal moment in your life that significantly influenced your personal development?
350. What’s the next big challenge you’re preparing to take on in your personal growth journey?
351. How do you measure success in your personal development, and have your criteria changed over time?

Pro Tip: While exploring these questions, be open to sharing your own experiences and insights. This mutual exchange can enrich the conversation, foster deeper connections, and provide mutual inspiration for personal growth.

Key Takeaways: How to Drive Conversation with Intriguing Questions

Everyone has differing levels of how much they’re willing to open up and share. Fortunately, there is a lot of ground to cover between “how was your day?” and “have you ever been in love?”

There are hundreds of questions you can ask someone without getting ultra-vulnerable, awkward, or nosey. Reading people’s body language and conversation cues is a great way to know what kinds of questions you want to ask next. 

A reciprocal give-and-take can make for an excellent deep conversation that brings you closer to your friends. 

Want to know how the pros use these questions to really become social masters? We’ve got you covered.