Friendship is one of the most meaningful and fulfilling parts of life. Spending time with our friends not only brings joy and laughter but also enriches our journey through adulthood.
However, with the hustle and bustle of daily life, it can be challenging to find the time and energy to connect with our friends meaningfully.
Introducing thought-provoking, hilarious and engaging questions to ask your friends can be an excellent way to strengthen your bond.
In this article, we have compiled a list of questions that can make your bond with your friends stronger, help you explore new realms of conversation and make memories that last a lifetime.
Contents
Juicy questions to ask your friends
Juicy questions to ask your friends328). Have you ever cheated on someone?
327). Is intimacy important for you to be in a relationship?
326). Have you ever been in love?
325). How much does your personality change when you’re around different people?
324). Tell me one of your most awkward moments.
323). Who do you wish you could reconnect with?
322). What’s one thing you would change about yourself?
321). Which activity do you prefer to relieve your stress?
320). Did you ever ditch someone?
319). What’s your life’s biggest regret?
318). What could be a valid reason for someone to cheat on their partner?
317). What’s the biggest lesson your last relationship taught you?
316). How do you define beauty?
315). With whom do you enjoy having meaningful conversations the most?
314). Who do you feel the safest around?
313). What can woo you instantly? Intelligence or physical appearance?
312). What’s the most bizarre text you’ve ever received?
311). Can you describe the most unusual text message you have ever received?
310). Fill me in with the numbers of your healthy relationships.
309). What do you think is the most annoying quality a person can have?
308). What’s the biggest leap of faith you’ve taken?
307). What is one key tip that you have learned from all your past relationships?
306). Have you ever tried any weird sexual activity?
305). What thing keeps you going on hard days?
304). What’s the cringiest thing you’ve ever put up on social media?
303). Are you a gossip queen/king? What is the latest gossip you have listened to and passed to others?
302). What’s an embarrassing thing you’ve done and never told anyone about?
301). Did you ever upload a cringe-worthy post on social media?
300). How would you define your type?
299). What is your definition of a deal breaker in a romantic relationship?
298). What is your definition of an ideal weekend?
297). What’s the cheesiest thing you have ever done for your ex?
296). When do you feel the most alone?
295). What do you prefer more: A big birthday party or a more intimate one?
294). If someone wrote a book about you, what would it be called?
293). What’s the weirdest thing you’ve done in public?
292). Do you believe in having one best friend?
291). What’s your favorite childhood memory?
290). Are you passionate about anything in your life?
289). What’s the nicest thing someone has done for you?
288). Do you believe in love at first sight?
287). What activity do you enjoy but feel guilty about?
286). Have you ever done any weird things? When, what, and where?
285). What do you feel the most guilty about?
284). What stresses you out the most?
283). Who do you think shouldn’t be a celebrity?
282). What was the last turning point in your life?
281). What is the most embarrassing memory you have of yourself?
280). Who is someone you wish you could apologize to?
279). Do you have any odd sexual fantasies?
Deep questions to ask friends
278). Is there a time when you did something that seems so out of character that most people wouldn’t believe it?
277). Looking back on your life, who or what makes you instantly light up?
276). Who are you most like in your family?
275). Would you rather people perceive you as being kind, smart or attractive?
274). What do you want people to know about you?
273). What is your greatest accomplishment?
272). What keeps you up at night?
271). How did you feel about where you grew up?
270). What are you most proud of about yourself?
269). What is the most trouble you’ve ever been in?
268). What keeps you up at night?
267). Who in your family do you struggle with?
266). How did you feel about where you grew up?
265). Would you rather people perceive you as being kind, smart or attractive?
264). Who is most important to you now?
263). What is the best piece of advice you’ve ever been given?
262). If you could meet anyone in the world, alive or deceased, who would it be?
261). Who sticks out as being an early positive influence in your life?
260). What do you feel has been your greatest “win” so far in your life?
259). What values are most important to you?
258). What is your greatest accomplishment?
257). How do you cope when things get hard?
256). How do you like to receive care?
255). What three words describe what you’re most grateful for?
254). If one wish of yours could come true, what would it be?
253). If you had a whole day where you could do anything you wanted, what would you do?
252). What makes your life feel purposeful?
251). What do you need less of in your life?
250). What do you need more of in your life?
249). Was it a supportive environment?
248). Looking back on your life, who or what makes you instantly light up?
247). What are you most proud of about yourself?
246). What is the best piece of advice you’ve ever been given?
245). What are you still hoping to accomplish?
244). If you could travel anywhere, where would you go?
243). If you had a whole day where you could do anything you wanted, what would you do?
242). Who in your family do you struggle with?
241). What would you like to accomplish in life?
240). What brings you joy?
239). How do you cope when things get hard?
238). What makes your life feel purposeful?
237). Who sticks out as being an early positive influence in your life?
236). What would you like to accomplish in life?
235). If you could meet anyone in the world, alive or deceased, who would it be?
234). Who are you most like in your family?
233). What really frustrates you?
232If one wish of yours could come true, what would it be?
231). What is the most trouble you’ve ever been in?
230). If you could travel anywhere, where would you go?
229). What really frustrates you?
228). What do you really care about?
227). What do you want people to know about you?
226). Who is most important to you now?
225). What do you really care about?
224). What brings you joy?
223). If you could leave a “mark on the world” that preceded you, what would it be?
222). What do you need less of in your life?
221). Was it a supportive environment?
220). How do you like to receive care?
219). What three words describe what you’re most grateful for?
218). What are you still hoping to accomplish?
217). If you could leave a “mark on the world” that preceded you, what would it be?
216). What do you feel has been your greatest “win” so far in your life?
215). Is there a time when you did something that seems so out of character that most people wouldn’t believe it?
214). What values are most important to you?
213). What do you need more of in your life?
Thoughtful Questions
212). Do you want to go to college in-state or out of state?
211). If you can give your parents one thing in the world, what would it be?
210). If you won the lottery, what would you do with the money?
209). If you could change one thing from your past, what would it be?
208). If you had to pack up and move to another country tomorrow, where would you go?
207). What career path do you see yourself taking in the future?
206). If you could have dinner with anyone dead or alive, who would it be?
205). What’s one conspiracy theory you actually believe?
204). If you had to fight for one global cause for the rest of your life, which would it be?
203). If you could travel back in time to any historical event, which would it be?
202). What’s one book that changed your life?
201). How do you prefer to be comforted when you’re upset?
200). What’s the first thing you notice when you meet a person?
199). If you had to curate the soundtrack to your life, what songs would be on there?
198). What’s your love language, Enneagram type, or Myers-Briggs type?
197). When you where younger, what did you want to be when you grew up?
195). What do you value most in friends?
196). Do you consider yourself an extrovert or an introvert?
194). Do you think there’s something that people misunderstand about you?
193). What do you think is your best quality?
192). What emotion do you feel the most?
191). Do you typically follow with your heart or your head?
190). Who is the first person you text when you get good news? Bad news?
189). Do you journal?
188). What social justice issues are you most passionate about?
187). Have you ever participated in a protest?
186). Do you consider yourself a religious or spiritual person?
185). Do you believe in love at first sight?
184). Do you feel like you act differently when you’re by yourself versus when you’re with a group of people?
183). What are you looking for in a friendship?
182). What is your definition of success?
181). What does happiness mean to you?
180). Do you think you’re hard on yourself?
179). What does your dream future look like?
178). What advice would you give to your younger self?
Fun (sometimes funny) questions to ask friends
177). What luxury item would you splurge on?
176). Would you rather be an expert at one thing, or pretty good at many things?
175). What is your comfort T.V. show?
174). What slang word do you wish would come back?
173). What movie or show do you keep rewatching?
172). Would you rather see five years into the future or 20 years into the future?
171). What’s been your most questionable haircut and/or fashion moment?
170). Do you prefer sweats or dressing up?
168). Do you believe in ghosts or any paranormal activity?
167). If you could have one superpower, which would it be?
166). What’s your skincare routine?
165). You just won $10,000 — what are you going to do with the money?
164). What was your first concert?
163). Have you ever been on a blind date?
162). If you were President, what’s the first thing you would work to change in this country?
161). What do you do when no one else is around?
160). Do you feel that you’re young at heart, or an old soul?
159). Do you like roller coasters?
158). If you could only eat one thing for the rest of your life, what would it be?
157). Do you believe in ghosts?
156). If you weren’t in your current profession, what would you be doing?
155). What foreign language(s) would you want to master and why?
154). What is your favorite ice cream topping?
153). If you could only eat at one restaurant for the rest of your life, what restaurant do you choose?
152). What book has impacted you the most?
151). What’s your favorite thing you own and why?
150). What’s the luckiest thing that’s ever happened to you?
149). If you could be famous for one thing, what would it be for and why?
148). Who is your favorite TikTok follow?
147). If you had to create an alter ego for yourself, who would it be and what would you name them?
146). What’s your favorite way to exercise?
145). Would you rather order in or eat out?
144). Did you ever go to summer camp?
143). Which book or movie impacted you most growing up?
142). What was the best date you’ve ever been on? The worst?
141). What’s your No. 1 karaoke song?
140). What’s your favorite holiday?
139). Who was your very first crush?
138). What makes you choose it? (See question above.)
137). What is the most exciting adventure you have been on?
136). Where is the most awe-inspiring place you’ve ever visited?
135). Do you believe in monogamy?
134). What is your most hated chore and why?
133). If you won the lottery, what’s the first thing you’d do?
132). Have you ever dreamed about what your children’s names would be?
131). If you could stay one age forever, what age would you choose?
130). If you could be any object, which would you be and why?
129). What does your ideal friend weekend look like?
128). If you had to change your name, what would your new one be?
127). What does your name mean, and why was it given to you?
126). When’s the last time you got to really experience nature?
125). Do you prefer cities or the countryside?
124). What’s your favorite holiday and why?
123). What was your AIM screen name, or your first email address?
122). If you could have a celeb as your BFF, who would it be?
121). If you could rummage through one celeb’s closet and take anything, whose would it be?
120). What’s your survival plan during a zombie apocalypse?
119). What’s an unexpected movie that makes you cry?
118). Do you prefer to stay in or go out on the weekend?
117). If you had three wishes, what would you wish for?
116). What are the qualities that attract you most in a love interest?
115). Where do you want to travel the most?
114). Do you want to study abroad?
113). What is the weirdest thing you’ve ever eaten?
112). Do you believe in aliens?
111). If money was no object, what would you buy?
110). Do you have any recurring dreams (or nightmares)?
109). What did you dream about last night?
108). What is your favorite memory?
107). If you could be the main character of any movie, what movie would it be?
106). If money was no object, what would you buy?
105). What songs would make up the soundtrack of your life?
104). If you were going to get some ink, what would you choose and why?
103). Would you rather be a famous musician or famous actor?
102). Do you have a hidden talent?
101). If you could take only one person on an all-expenses-paid vacation, who are you taking?
100). What is your idea of the perfect proposal?
99). If you were elected President, what would be your first act?
98). Have you ever had your fortune told?
97). If you could trade places for someone for the day, who would you choose and why?
96). What’s your favorite piece of random trivia?
95). What’s the first thing you do when you wake up in the morning?
94). Who is your favorite musician or band?
93). If you could revive fashion trends from one particular decade, which would it be?
92). What hobby would you like to try out?
91). What song could you listen to on repeat for the rest of your life?
90). Would you rather drink coffee or tea for the rest of your life?
89). What’s your favorite podcast?
88). What beauty or fashion moment do you regret most?
87). What’s your favorite childhood memory?
86). You can only use TikTok or Instagram — which one do you choose?
85). What is your comfort movie?
84). What’s the worst date you’ve ever been on?
83). Would you rather live by the beach or up in the mountains?
82). If you could live in any period of history, when would it be and why?
81). What are two places you want to go before you die?
80). If you had to choose only one, would you pick a dog or a cat?
79). What’s the funniest joke you’ve ever heard?
78). If you had to live in another time period, what would you choose?
77). Which decade, in your opinion, had the best fashion trends?
76). What instrument would you like to learn how to play?
75). If you were an animal, what would you be?
74). When was the moment in your life you laughed the hardest?
73). If you could delete all social media apps and go off the grid, would you?
72). What was your favorite game as a child?
71). What’s your all-time favorite dessert?
70). What’s your favorite commercial?
69). Be honest — what is the last thing you searched on your phone?
68). What was the first movie you remember seeing in theaters?
67). If you could only eat pizza, wings or burgers for the rest of your life, which would you choose?
66). What is on your bucket list?
65). If a song played every time you entered a room, what would it be?
64). If you could eliminate one subject from school, what would you choose?
63). Would you rather time travel to the past or the future?
Random questions to ask friends
62). If you are drowning, who do you think would save your life?
61). How would it feel to cry underwater?
60). Have you experienced being confined in a hospital?
59). Have you ever composed a song?
58). What do you hate about me?
57). Do you have any kids?
56). What are the qualities you search for in other people?
55). What are the challenges you never gave up on?
54). Who is your childhood best friend?
53). Have you ever gotten a speeding ticket?
52). Who eats the most in the family?
51). Do you like chocolate?
50). Which of the Seven Dwarfs resembles you the most?
49). What is the worst punishment your parents gave you?
48). Do you get thirsty in the middle of the night?
47). What’s the worst food you’ve ever eaten?
46). Have you experienced falling down the stairs?
45). Do you like cilantro?
44). How many countries have you visited so far?
43). What makes you really angry?
42). Have you ever stolen food from the refrigerator and blamed it on someone?
41). Who would you want to portray your life story in a movie?
40). If you were a pair of shoes, what brand would you like to be?
39). What’s the most valuable thing you’ve learned in life?
38). Did you ever go to college?
37). What do you like most about going to the beach?
36). What’s the last thing on your bucket list?
35). Which fictional book character would like to meet in the future?
34). Have you ever kept a journal?
33). Without calling 911 when you are in danger, what would you do instead?
32). What is the most embarrassing moment you had in your workplace?
31). How many times have you traveled by sea?
30). Do you believe in ghosts?
29). What’s your favorite car brand?
28). Who has taught you the best lesson in life?
27). Do you have a best friend?
26). Do you own bitcoin?
25). What’s the extreme challenge in your life that you’ve already overcome?
24). What habits of other people do you definitely find disgusting?
23). Do you still keep secrets from mom/dad?
22). What is the best song to describe your life right now?
21). What is your current favorite TV show?
20). Have you ever been on TV?
19). Do you sing in the shower?
18). Where do you see yourself in the next 5 years?
17). If you were given the chance to kiss and hug someone, who would that be?
16). How was your wedding?
15). What is your most cherished possession?
14). Do you like to exercise regularly?
13). Has anyone tried to kill you?
12). Do you believe in aliens?
11). Do you pay attention to the news?
10). Have you ever thought of having plastic surgery?
9). Have you ever had deja vu?
8). Do you like your job?
7). What would you do if you knew you’d be good in a different profession?
6). What is one piece of advice you wished you’d seriously taken?
5). What’s your dream job?
4). Do you ever talk to yourself in your head?
3). Do you live alone?
2). What sound do you hate?
1). What is your favorite dance move when you were a kid?
Conclusion
These are just some of the questions you can ask your friends to get to know them a little bit better. Whether it’s a casual conversation or a deeper dive into the lives of those around you, getting to know your friends and family is an important part of life.
Asking thoughtful, meaningful questions can help break down walls and open up conversations that create lasting relationships. With this list of 300+ questions, there’s something for everyone!
