Even if you know your closest friend really well, I’m gonna assume that there’s probably plenty of lore that they still haven’t dropped. And it’s not always because they’re trying to hide something; it just doesn’t always make sense to bring it up when you’re hanging out.
But if you do want to go a little deeper, connect, or just learn something interesting (or funny) about them, then this list of good questions to ask your friends is a great place to start.
And whether it’s a one-on-one or a small group of besties, this Q&A session has the potential to strengthen your friendship bonds and even get hilarious answers out of them.
This list is also built with different moods and different kinds of people in mind.
So for instance, you have interesting questions to ask friends so that you can keep away from small talk, fun questions to ask friends to start a good conversation, deep late-night talks with BFFs, and even questions for getting closer to a new friend.
Also, being a good friend just means that you care and you actually wanna get to know them even more. You’re asking questons to really understand them, how they think, and what their hopes and dreams are. So if you wanna make that connection stronger and get even closer, then here are some of the best questions to ask your besties.
Do a fun question date with them this month and build a much healthier (and more fun) friendship!
In This Article:
- Fun Question to Ask Friends to Start Good Conversations
- Deep Questions to Ask Friends for a Stronger Bond
- Juicy Questions to Ask Your Friends (That Aren’t Cringe)
- Questions to Ask Your Best Friend for the Deepest Late-Night Talks
- Random Questions to Ask Your Friends
- Interesting Questions to Ask Friends And Avoid Small Talk
- Questions to Ask a New Friend & Get Closer
Fun Question to Ask Friends to Start Good Conversations
1. If you could swap lives with a cartoon character for a whole week, who would you go for?
2. What’s the weirdest food combo that you secretly really love?
3. If you had a theme song that played every single time you walked into a room, what song would it be?
4. What’s a trend you actually liked, but felt too embarrassed to hop on it?
5. If you could be famous for literally anything, what would it be and why?
6. What’s the most ridiculous or funny thing you believed when you were a kid?
7. If you could teleport to any country to eat a specific type of food, where and what would it be?
8. What’s your personal go-to karaoke song, and do you own it or kind of just survive it?
9. If you could bring back literally any fashion trend for just one day, which one would it be?
10. What’s a movie you could legit quote from beginning to end?
11. If you had your own mascot that followed you around, what would it even look like?
12. What’s your signature dance move you do no matter what (and what’s it called)?
13. If you’re gonna survive a zombie apocalypse with up to three fictional characters, who are you choosing?
14. What was your most iconic and your most cringe Halloween costume as a kid?
15. If your life became a reality show, what would you call it?
16. What’s a pretty cool fun fact you know that a lot of people don’t?
17. You were just accidentally recruited into a spy agency. Would you take the mission they gave you, or just fake your own death?
18. What’s the strangest but nicest (or weirdest) compliment you’ve ever received?
19. If your pet suddenly had the ability to talk, what’s the very first thing they’d probably say to you?
20. What oddly specific genre of shows or movies is your favorite? Example: Cozy mysteries set in an English village.
21. If you’re a movie villain, what’s your over-the-top evil plan gonna be?
22. What’s your favorite guilty pleasure song that you will always refuse to feel guilty about?
23. If you could make just one completely useless skill into a job that makes really good money, what would it be?
24. What’s probably the funniest thing that’s ever happened to you when you were out in public?
25. If you had to create a holiday that everyone needed to celebrate, what would it be about and how would people celebrate on that day?
26. What’s the worst or strangest name you’ve ever heard given to a pet?
27. If you had to wear just one outfit for the rest of your life, what would you choose?
28. What’s your ultimate comfort movie ever? Like the one you put on when you really just need to feel good?
29. If you had a million dollars right now, but you had to spend it all in just 24 hours, what would you be spending it on?
30. If you ended up living in the setting of the last book you read, where would you be right now?
31. What’s your current “I didn’t expect to actually love this” hobby or interest?
32. What’s a smell that instantly brings back a really good memory?
Deep Questions to Ask Friends for a Stronger Bond
1. What’s a moment or experience in your life that changed you forever, and no one even noticed?
2. When or where do you feel most like yourself?
3. What do you really wish people understood better about you right now?
4. Have you ever had a friendship break your heart?
5. What’s something you’ve forgiven but still can’t forget?
6. What’s one big fear you’ve overcome that you never thought you would?
7. What does “home” mean to you personally? Like is it a place, a person, a feeling?
8. If you could give your younger self just one piece of advice, what would you say to them?
9. What’s something small that means way more to you than people will ever realize?
10. Is there a memory you go back to during moments when you need comfort?
11. What kind of legacy do you personally want to leave behind? Even in small ways?
12. What’s a personal belief or core value you have that’s been tested but never shaken?
13. Do you think people can ever really change, or can they only adapt?
14. What’s something you’ve never been able to tell anyone because it felt too vulnerable and scary?
15. How do you personally define success in life, and has your definition changed over time?
16. What does love personally feel like to you? And this can be in all of its forms: romantic, platonic, and familial.
17. Is there a part of your personality that some people tend to misunderstand?
18. What’s something you thought you’d have figured out and gotten down by now, but haven’t?
19. When was the last time you actually felt seen? Like someone legit got you, and got you completely?
20. What’s a life choice you’re super proud of, even if you or others would say it wasn’t a “smart” one?
21. If you could relive just one year of your life and be able to enjoy it all over again, which year would you choose?
22. What’s something that legit scares you? Not because it’s dangerous, but because it feels a little too real?
23. How do you tend to handle emotional pain when you know that you can’t fix the problem?
24. What kind of person do you want to be remembered as when you’re gone?
25. When do you feel the most at peace with yourself and everything around you?
26. What do you personally think happens after we all die?
27. What do you think is the difference between being alone and being lonely in your personal experience?
28. Who do you feel has shaped your values the most in life, even if you’re not talking to them anymore?
29. What specific emotion have you always found the hardest to express, and why?
30. Even if it’s not linear, what does healing personally look like to you?
31. Is there a certain part of yourself you’re still trying to reclaim or discover right now?
32. When do you feel the closest to the people you care about? Like what moments make it so much more real?
Juicy Questions to Ask Your Friends (That Aren’t Cringe)
1. Who was your biggest crush when you were growing up? What did you like about them?
2. Has a good friendship ever turned into something more?
3. What’s a big or small secret you never told your parents when you were a teenager?
4. What was the most unpredictable crush you’ve ever had? Like you just didn’t see it coming?
5. Were there ever sparks with someone at the worst time possible? What did you even do about it?
6. Have you ever caught strong feelings when you knew you weren’t supposed to?
7. What’s something good or bad that you almost did that would’ve completely changed your life?
8. Have you ever regretted saying no to a person? This could be someone who was interested in you, or something completely different.
9. Have you ever just kissed someone and then instantly realized it meant a whole lot more than you thought it would?
10. What’s a super romantic moment in your life that you know could’ve been a movie scene?
11. Have you ever had to make a choice between a friend and someone you were dating at the time?
12. What is something you would never ever do for love, no matter how strong your feelings were?
13. Who was your very first kiss, and how do you feel it went?
14. Have you ever had one of those “What was I even thinking?” moments with someone you really liked?
15. What’s a time you felt completely irresistible? Even if it was just for a moment?
16. Have you ever found yourself in a love triangle (even if no one actually knew)?
17. What’s your most random story where you were flirting with someone?
18. Have you ever had a crush that legitimately shocked you? Like, “Wait, them?”
19. What’s probably the biggest risk you’ve ever taken with your love life and dating?
20. What’s your “type” right now, and how has it changed over the years?
21. Have you ever had really strong feelings for someone, but just never told them?
22. What’s your personal biggest green flag and red flag when dating?
23. Has a dream ever made you wonder and question your feelings for someone in real life?
24. Who’s the one person you always thought something might just happen with them… but then it never did?
25. What’s a single moment you replay in your head a lot more often than you’d like (or like to admit)?
26. What’s an action you’ve done for love that legit surprised even you?
27. Have you ever been in a friendship where the chemistry was just a little too good?
28. What’s one song that instantly brings back a specific memory with someone you dated?
29. Have you ever been really jealous of a friend’s relationship? How did you end up handling it?
30. What’s one big thing you wish more people would just admit about love or attraction?
Questions to Ask Your Best Friend for the Deepest Late-Night Talks
1. What’s one thing you’ve never told anyone about, but you kinda wanna say out loud?
2. Do you personally believe that we ever meet people by fate, or do you think it’s all just chance?
3. What’s a moment in your life where you were the most scared, and did you ever tell anyone about it at the time?
4. If you could ask God just one single question and get an answer, what would you ask Him?
5. What’s something or someone you let go of even though it was ridiculously hard?
6. Have you ever gotten the feeling that you were living another person’s version of your life?
7. What’s a powerful memory you don’t really talk about much, but just wish someone would ask you about?
8. Do you believe people tend to be mostly good, or are they just doing their best?
9. What do you believe your younger self would think of you at this very moment?
10. What’s the single hardest truth you’ve ever had to come to grips with and accept about yourself?
11. When was the last time you cried in front of someone? And did you feel a lot of relief or regret?
12. Do you personally believe that there’s a difference between being loved and being seen?
13. What’s one thing you’re afraid of people finding out about you?
14. What’s probably the kindest thing someone’s ever said to you and has always stuck?
15. If you could relive just one conversation in your life, word for word, which one would you choose?
16. Even if it’s hard to ask for, what do you need a lot more of in life right now?
17. Is there someone you feel that you can never forgive?
18. What does (non-romantic) intimacy personally mean to you?
19. What’s your “safe place?” Like, is it a moment, a place, or a person?
20. What’s a truth about friendship you ended up learning the hard way?
21. What’s one thing you wish people would just stop assuming about you?
22. Do you feel that you’ve ever lost a part of yourself just trying to keep someone else in your life?
23. When was the loneliest you’ve ever been?
24. What’s something you’re still healing from, but you just never talk about it?
25. What do you think is your best trait (and your worst one)?
26. Is there a version of your life you’ve always secretly wondered about?
27. What do you think your soul needs a whole lot more of these days?
28. When was the last time you really felt understood by someone?
29. What’s a strong belief you have now that you actually fought against for a pretty long time?
30. When we’re in our 80s, what do you personally think we’d remember the most about right now?
Random Questions to Ask Your Friends
1. If animals could talk, which do you think would be the most annoying species?
2. What would you do if you woke up one day and everyone had suddenly switched names (but no one else noticed for some reason)?
3. What’s the weirdest and craziest dream you still remember in really vivid detail?
4. If you were a kitchen appliance, which one do you think you would be and why?
5. Would you rather have a fight with one horse-sized duck or 100 duck-sized horses?
6. What’s one thing you’ve always wanted to try but could never explain why?
7. If you had to live inside a movie universe for one whole year, which one would you be going for?
8. What’s the strangest compliment you think you’ve ever gotten?
9. If your thoughts suddenly became visible in cartoon bubbles above your head, how often would you be getting in trouble?
10. What’s a conspiracy theory you don’t actually believe, but you find it to be super fascinating anyway?
11. If you had to replace your hands with garage tools, what would you decide on?
12. What’s a food or drink you really love that almost everyone else seems to hate?
13. If your life became a video game, what would probably be your weirdest power-up?
14. Would you rather never be able to wear socks ever again or never be able to have warm food again?
15. If you instantly became an expert in something totally ridiculous, what would it be?
16. What’s your go-to excuse for when you really don’t wanna go out but you also don’t wanna hurt someone’s feelings?
17. What’s a word you’re always spelling wrong even though you actually know better?
18. If you were told to do a TED Talk on something completely random, what topic could you yap about for 20 minutes?
19. If you could only wear just one color for the rest of your life, what would you choose?
20. What’s probably your most irrational fear ever? Like, totally harmless but still pretty scary?
21. If you had to rename everyday household objects with new words that you just made up, what would you call a pillow?
22. If you came with a warning label, what would it say about you?
23. If you had to choose just one day out your life to be stuck in a time loop, which one would it be?
24. Which would you rather have the ability to do? Taste music or smell colors?
25. If you didn’t have your name, what name feels like it should probably be yours?
Interesting Questions to Ask Friends And Avoid Small Talk
1. What’s one decision you made that felt pretty small at the time, but ended up changing basically everything?
2. If you could instantly master just one skill only for fun (not for profit), what would it end up being?
3. What’s some random memory or bit of trivia that pops up in your head a lot more often than it should?
4. Have you ever experienced a moment where almost everything kind of just felt weirdly aligned?
5. What’s one place that completely took you by surprise in the best or worst way?
6. If you had to live just one year of your life on repeat, which year would you choose?
7. What’s something you secretly judge people for (even though it’s small)?
8. What’s something people always assume about you, and they’re right (but you wish they weren’t)?
9. Have you ever had a good or bad friendship that actually changed the way you see the world?
10. If you could be famous for something that’s kind of unusual, what would you want that thing to be?
11. What’s legit the best compliment you’ve ever received that wasn’t even about your appearance?
12. If your life suddenly became a novel, what would the title of your current chapter be?
13. What’s something you’ve always wondered about, but just never thought to ask anyone?
14. What’s a single moment in your life you just wish you could bottle up and relive on hard days?
15. If you had to give your own personal aesthetic a name, what would you call it?
16. What’s your personal “comfort internet rabbit hole?” Like the kind of topic you can always get lost in?
17. When was the last time you really felt out of your element, and how did you decide to handle it?
18. What’s a big way of looking at things that you’ve changed your mind on over the years?
19. If someone were to narrate your entire life, who would you want the voice to be?
20. What’s a lie people keep telling themselves that you just wish they’d stop believing?
21. What part of your personality has changed since you were a little kid?
22. What’s one moment that had you laughing way harder than it should have?
23. What’s one thing you thought was completely normal growing up, but now realize that it was completely unique?
24. If you had your own personal motto, what would it be?
25. What’s one thing you think more people really should try at least once in their lifetime?
Questions to Ask a New Friend & Get Closer
1. What’s something that always makes you feel better when you’re having a bad day?
2. Do you consider yourself to be more introverted or extroverted (or just somewhere in between)?
3. What’s something a lot of people don’t know about you just from meeting you?
4. What’s something you’re super passionate about that people probably wouldn’t expect?
5. What does your perfect weekend look like?
6. What type of conversations make you feel really connected to someone?
7. Do you have a personal “comfort show” or movie you go back to on repeat?
8. What’s one quality you really admire when you see it in other people?
9. What’s your personal go-to way to recharge when you’ve had pretty a long day?
10. Is there a song that kind of just feels like a snapshot of your personality?
11. What’s something you’ve always wanted to learn up on or try, but just haven’t done it yet?
12. Do you remember that one moment that made you feel like someone actually got you?
13. What kind of friendship do you really appreciate and value the most? Like daily contact, deep convos, shared adventures, or something else?
14. If you had to plan out the perfect day with someone new, what would you end up doing together?
15. What’s just one small detail that really helps you to feel seen and/or appreciated?
16. How do you personally show someone you care about them (words, time, gifts, etc.)?
17. What’s one thing you wish people would just ask you more often?
18. Is there a good book, quote, or movie that’s really stuck with you for years?
19. What’s your personal love language in a friendship?
20. Have you ever had a friend who legit came right into your life at just the perfect moment?
21. What’s something that makes you feel instantly comfortable with someone new?
22. What’s your favorite kind of night at home?
23. When are you feeling your most confident?
24. What’s your personal idea of a real friendship (the non-Instagram version)?
25. What’s probably the kindest thing someone’s ever done for you, and you’ve never forgotten?
26. What’s something you’re working on in yourself right now that you’d really love support for?
Want More Question Game Ideas to Play With Your Friend?
- Would You Rather Questions That Reveal A Lot About You (And Others)
- Best “Never Have I Ever” Questions for the Funnest Game Night Ever
- 250 Truth or Dare Questions to Fit the Mood, No Matter How Extra or Chill
- 170 Best ‘Most Likely To’ Questions for Friends, Partners, & Everyone Else
- 200 “This or That” Questions for Friends, Dates, & Late Night Conversations
Grace Moser is the author and founder of Chasing Foxes, where she writes articles to help women create a life they love in big and small ways. She's been a full-time traveler since 2016 and loves sharing her experiences and exploring the world with her husband, Silas. Her lifestyle and travel advice can also be seen on sites such as Business Insider, Glamour, Newsweek, Huffpost, & Apartment Therapy.