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300 Questions to ask your friends

Welcome to our questions to ask your friends page. We’ve got 300 questions for you that span five categories. With so many questions, you are sure to find the perfect set of questions for your friends.

A few quick notes of caution:

  • Keep in mind that some of the juicy questions are adult themed and meant for a mature audience.
  • The juicy questions are also designed to make the answerer very uncomfortable. So if that isn’t what everyone is looking for, give that section a pass.
  • The deep questions to ask your friends can get very serious and may cover some sensitive topics.

Juicy questions to ask your friends

  1. What unconventional thing do you find attractive?
  2. When was the last time you got stood up?
  3. What was the most embarrassing or sloppy night out you had?
  4. What’s the weirdest thing you’ve done in public?
  5. What embarrassing thing have you done that you never told anyone about?
  6. What’s your grossest habit?
  7. What’s the biggest lie you told a romantic partner?
  8. What don’t your parents know about you?
  9. What’s the strangest thing you’ve tried in bed?
  10. What’s the most bizarre text you’ve received?
  11. Has anyone ever cheated on you?
  12. Who do you pretend to like but actually don’t like?
  13. Who is the most toxic person in your life?
  14. What embarrassing thing did you do regularly when you were a kid?
  15. Have you ever hooked up with someone who smelled bad?
  16. What is the cringiest thing you’ve put up on social media?
  17. What’s the worst hair cut you’ve had?
  18. Have you ever had a crush on a cartoon character?
  19. When was the last time you crapped your pants?
  20. What was your worst rebound?
  21. What is the worst fight you’ve been in?
  22. Do you get jealous if your partner hangs out with or is friends with people of your gender?
  23. What was your biggest fear as a child?
  24. Have you ever hooked up with someone and you didn’t know their name?
  25. What was your biggest mistake?
  26. When did your hubris get you into serious trouble?
  27. What is the most detestable thing you would do for 1 million dollars?
  28. What do you feel most guilty about?
  29. What embarrassing thing have your parents caught you doing?
  30. What are you self conscious about?
  31. What’s the most serious crime you’ve committed?
  32. Who’s most to blame for your baggage?
  33. Have you ever had a crush on a romantic partner’s friend?
  34. What’s the most awkward date you’ve been on?
  35. What lie do you tell yourself most often?

If you are looking to make the questions more of a game, why not try our never have I ever questions or our truth or dare questions.

Random questions to ask your friends

  1. What do you want your retirement to look like?
  2. What’s the best way to spend a vacation?
  3. How much of an open book are you?
  4. When are you most in your element?
  5. What’s your way to vent stress?
  6. Where is the most spectacular place you’ve been?
  7. How important is looking good to you?
  8. What was or is your favorite piece of clothing?
  9. What famous person do you admire?
  10. Would you ever open a business? If so, what type?
  11. What’s your outlet for creativity?
  12. What’s the most annoying thing you have to deal with on a daily basis?
  13. What do you take for granted?
  14. What do you consider pretentious?
  15. What do most people just not get?
  16. What did you learn too late?
  17. What lesson was hardest for you to learn?
  18. Who got a reputation they didn’t deserve?
  19. What food do some people consider normal but you think is gross?
  20. What did you learn way later than you should have?
  21. What is something that everyone seems to love but you hate?
  22. When was a time you were terrified?
  23. Where do you feel most at home that isn’t home?
  24. Who do you wish you could reconnect with?
  25. What is the best present you’ve gotten?
  26. When was a time you were falsely accused of something?
  27. What small slight are you still upset about years after it happened?
  28. What aged like milk?
  29. When did you fake it till you made it?
  30. Who depends on you the most?
  31. What are your tribes?
  32. How adventurous do you think you are?
  33. When was the last time you did karaoke?
  34. What is the most annoying new “innovation“?
  35. How often do you get into political arguments with people?
  36. What has changed most since you were a kid?
  37. What do you think you’ll be like when you are old?
  38. How do you think other people view you?
  39. What’s the worst holiday?
  40. What competition do you think you’d be most likely to win?
  41. What’s the funniest band name you’ve heard of?
  42. If you were in charge of designing a public park, what would it be like?
  43. What upgrades to your belongings would you like to make?
  44. What was/is your favorite pet?
  45. What irrational fear do you have?
  46. What is your go to snack or a snack you have a hard time stopping once you start?
  47. What is the most tedious thing you have to do on a regular basis?
  48. What’s is the coolest decorative thing you own?
  49. Who much did/do you like or hate school?
  50. How comfortable do you feel in a crowd?
  51. Do you think dreams have any significance or is it just your brain doing maintenance?
  52. What job are you uniquely qualified for?
  53. What questions should people ask each other more often?
  54. What are some of your personal rules?
  55. What are some of the worst things that people do to your favorite foods?
  56. What are some of the best examples of the illusion of safety in daily life?
  57. How much do you rely on other people?
  58. What is you most treasured possession?
  59. How gullible are you?
  60. What is the funniest haircut you’ve seen in the wild?
  61. What are some of the benefits of growing old?
  62. What’s the spiciest thing you’ve ever eaten?
  63. What type of personality do you find most exhausting to be around?
  64. What defines you most as a person?
  65. Who is the funniest person you know?
  66. Regardless of your age, what is your best “kids these days” rant?
  67. What is the dirtiest bathroom or house you’ve seen?
  68. What is the dumbest thing you’ve seen someone do in person?
  69. What idea or ideas would you love to act on if you had the time, money, and/or know how?
  70. What is something that happened recently that took you completely off guard?
  71. What are you putting off?
  72. What is your best story about one of your teachers?
  73. Do you think the present is better than 15 years ago? Why or why not?
  74. What kind of first impression do you think you give?
  75. What are some of the most “backwards” things about your country, how about some of the most “progressive” things?
  76. How do you feel about the direction your life is headed?
  77. What do you think of the advances in AI, optimistic or nervous?
  78. Do you believe in absolute truth?
  79. What kinds of beliefs or values have shaped history the most?
  80. Do you think once an invention becomes possible, it’s inevitable that someone will invent it?
  81. How accurate do you think some of the stereotypes are for certain countries? What stereotypes do people have about your country?
  82. Do you think the place where you get your news presents an accurate picture of the world? How could it be improved?
  83. How could your work or school be better than it is now?
  84. What do you think about your/our country’s tax system?
  85. What do you consider to be some prestigious jobs? Do you think you would be good at any of them?
  86. Would you ever volunteer to join the military?
  87. What, besides posture, do you constantly have to remind yourself of?
  88. What radically new forms of government can you think of?
  89. What kind of long-term career goals do you have, if any?
  90. What do you need more practice doing?
  91. How much of a person’s personality is up to them and how much is just who they are?
  92. Why do you think people like the things they like? Is it all environmental influence or do you think some preferences are genetic?
  93. What did your hideouts look like when you were a kid?
  94. What dressings do you choose for different types of food? (Salad, wings, baked potatoes, etc.)
  95. What are some things you began but never finished?
  96. What kind of advantages does your personal history give you?
  97. What do you need a crash course in?
  98. How important are borders when it comes to countries?
  99. What’s your opinion on cabins? Creepy, cozy, or somewhere in between?
  100. What do you half ass that maybe you should whole ass?
  101. What just isn’t fair?
  102. How tenacious are you?
  103. What totally wrong search or social media algorithm choices have you had a hard time shaking?
  104. How good are social media algorithms with your tastes?
  105. If you had a big red button, and could assign it to do one thing every time you pressed it, what would you want it to do?
  106. What elaborate prank do you wish you could pull on someone?
  107. What leaps of faith have you taken and how did they turn out?
  108. What do you think the most annoying thing you do on a regular basis?
  109. What would you say is your best quality?
  110. What function of the body do you wish we do away with?
  111. What totally wrong search or social media algorithm choices have you had a hard time shaking?
  112. What elaborate prank do you wish you could pull on someone?
  113. What leaps of faith have you taken and how did they turn out?
  114. What do you think is the most annoying thing you do on a regular basis?
  115. What would you say is your best quality?
  116. How good are social media algorithms with your tastes?

For more random questions check out our conversation starters page or our good questions to ask page.

Weird questions to ask your friends

  1. If existence is just a simulation, what would be the name of the game?
  2. What would be the most disturbing thing to throw up?
  3. If you could change the sound of your farts, what new sound would you pick? (Silence doesn’t count.)
  4. What would the creepiest horror monster be like?
  5. If you had to sleep on food every night, what food would you choose?
  6. What kind of tail would you want if you had to get one?
  7. What would be a better name for a brain?
  8. What would be the funniest thing to randomly come out of your shower head while taking a shower?
  9. If you had to design a completely new instrument, what would it be?
  10. If body parts could talk, what would different ones say?
  11. What would be the most inconvenient thing to make a house out of?
  12. What would the be the funniest animals to train to dance?
  13. What would you wait in line for a week to get?
  14. How would you make funeral fun? A “fun”eral if you will.
  15. If you could change a planet in our solar system into an object that would keep the same planetary size and mass, what object would you choose?
  16. What food would you want to grow from your hands instead of fingers?
  17. If trees could talk, what would they sound like?
  18. When is reality least real for you?
  19. Where would be a cool place to throw some more joints and muscles in our bodies?
  20. If you could be half animal like a mermaid or centaur, what animal would you choose?
  21. Where would be the funniest place to make 1 ton of pudding instantly appear?
  22. If people’s names had to be changed to accurately describe the person, what would our new names be?
  23. Which condiment would be the funnest to swim in and which would be the worse?
  24. What would you do with a mirror that shows what your body looks like beneath the skin?
  25. If you could start a new fashion trend and no matter how silly it was people would take it seriously, what would be the funniest trend to start?
  26. If you found a new species (your choice of what it is/looks like) and got to name it, what would you name it?
  27. What would you do with the super power of whatever living thing you touch farts?
  28. What mythical creature do you wish you had as a pet?
  29. What is the most trouble you could get into with a 200 pound bag of those polymer beads that grow in water?
  30. If tattoos could move and loop like gifs, what would be the most annoying thing to get tattooed on you and where?
  31. What could you do to make a good tasting desert pasta? The one rule being it must use normal pasta.
  32. What competition would you like to create and what would the trophy look like? And remember you can at anytime in you life just buy a trophy for yourself or someone else.
  33. Sunscreen protects you from the sun, what other things do you wish you could defend against with a daily applied cream?
  34. If you were trapped in a room for a week, and the walls ceiling and floor were painted one color, what would the best and worst color for the room to be?
  35. Where do you fall on an alignment scale? *
  36. If you could be anywhere in the world when a 50 mile in diameter impenetrable (except for liquids and gases like air), inescapable, eternal bubble appeared with you in the exact center, where would you want to be standing?
  37. Would you want to be put into a comfortable alien zoo and be a small part of a larger universe? Or keep your autonomy and not know if aliens exist or not?
  38. If you became famous and a city wanted to make a statue of you, what pose would you want to be in?
  39. What expression would you like to be in popular use and what would it mean / how would it be used?
  40. If you were born 500 years ago (and made it to adulthood), what kind of job do you think you’d be good at?
  41. Can you give me an example of a great but bad idea?
  42. What’s the funniest thing you could shoot 
  43. from a cannon?
  44. If you got 5$ for every minute you sat without moving how long do think you could sit?
  45. What keeps you going?
  46. When was one of the most inopportune times you farted?
  47. What are some things that would seem really weird if they were turned a different color?
  48. What household object best represents your personality?
  49. If you had a personal flag, what would it look like?
  50. If you were given a free sitting for a very large and professional painted portrait of yourself, how would you want yourself to be portrayed?
  51. You find a trap door hidden in your house or apartment, what do you hope to find inside? What are you afraid you’ll find inside?
  52. What would be the worst thing to make a sofa out of?
  53. What kind of crazy ad campaign would you like to see a company run? Even if it means driving the company into the ground.
  54. What crazy or stupid statue would you like to see put up?
  55. What would be the weirdest thing to find in the basement of a hospital?
  56. Would you be a hermit with no technology and no human interaction for 5 years but you were paid 100k a year and food and cave were included?
  57. If you had a disease named after you, what would you want the symptoms to be?
  58. What is the grossest thing you could have a vat full of?
  59. What mythical creature creeps you out the most?
  60. What would be the most fun yet efficient way to move people around a big city?
  61. What would be the most entertaining way countries could settle their disputes?
  62. If you had a big red button, and could assign it to do one thing every time you pressed it, what would you want it to do?
  63. What function of the body do you wish we do away with?

For more weird questions try our weird questions to ask a guy, weird questions to ask a girl, or funny questions.

Deep questions to ask your friends

  1. Where does a person’s worth come from?
  2. When things go wrong do you blame yourself or others more?
  3. How much does your personality change around different groups of people?
  4. What are some of the turning points of your life?
  5. How often do you leave your comfort zone?
  6. Who do you turn to when things get bad?
  7. Who causes you the most stress?
  8. What does our society need most?
  9. What dream did you give up on?
  10. Who do you wish you could apologize to?
  11. What is your self destructive habit?
  12. What is taboo that shouldn’t be?
  13. When was the last time you were ashamed by how you handled a situation?
  14. What do you fear most?
  15. What are some good and bad things about the culture you grew up in?
  16. What kind of parent do you think you’d make? Or if they have a kid, what’s different about parenting than what you expected?
  17. How good of a person are you?
  18. How can we know if how we perceive colors is how others perceive that color? How do we know that colors don’t look different to everyone?
  19. Why do some people crave power over others?
  20. How well do you think the mind can understand itself?
  21. What flaws in human nature hold humanity back?
  22. How much control do we have over the workings of our autonomous body functions do you think we have?
  23. When do you feel most alone?
  24. What are you most insecure about?
  25. How would we tell if we were actually living in a simulation?
  26. What responsibilities, if any, do tech companies have to control how people use their platforms and what content shows up on them?
  27. How do you think our friendship will change over time as we get older and our life circumstances change?
  28. What would the colors of infrared and ultraviolet look like if we could see them?
  29. How do you deal with trauma?
  30. Why do you think people feel so empty in the modern world, or is this how it’s always been?
  31. Do you think shame is a natural human emotion or something that society drills into us?
  32. What do you think the evolutionary reason is for humans basing so many of their choices on emotions?
  33. Why do humans create art?
  34. What is your reason for getting out of bed in the morning?
  35. Do you think animals have a sense of right and wrong or is it just humans?
  36. How big of a part should work be in a person’s life?
  37. What causes are most deserving of people’s time and charity?
  38. Are wars inevitable as long as humans exist?
  39. What do you think is the secret to keeping a child like sense of wonder and avoid becoming jaded?
  40. What’s is the biggest impediment to innovation?
  41. How do you think the discovery of extraterrestrial intelligent life would impact society?
  42. How much does your past define you?
  43. What is the most worthwhile personal goal to work towards?
  44. What are the biggest factors in a smoothly running society?
  45. Why do you think humans find round numbers so appealing?
  46. Why do you think most people are nervous about change? Do you think humanity would be better off if we were quicker to embrace change or do you think we would have been wiped out as a species?
  47. What do you need help with the most?
  48. Who do you think actually knows what they are doing and has a good handle on things?
  49. What things do you feel like you’ve lost as you’ve gotten older? What do you think you’ve gained? (Not like socks, more like a sense of purpose or faith in humanity.)
  50. What do you think is worth going to war over? Would that change if you or your children had to fight versus if other people had to?
  51. What do you think your country could use more of and what could it use less of?
  52. What do you consider to be your biggest failure?
  53. Is it ever possible for a reporter to be completely unbiased? Do you think you would enjoy news that was totally unbiased?
  54. How important is having a status quo for society?
  55. How do you think our country will fare in the next five years?
  56. What do you think the some of the most important things a city government can do for its residents?
  57. What do you have a hard time accepting?
  58. What or who are you most loyal to?
  59. How do you decide if a person can be trusted?
  60. Why do you think people have a hard time appreciating what they have until they lose it?
  61. What makes you believe or not believe in fate?
  62. What do you want your funeral to be like?
  63. How well do you know yourself?
  64. What lies do you tell yourself?
  65. What have you become disenchanted by?
  66. What does healthy conflict or disagreement look like?
  67. What would you want on your tombstone?
  68. Why do you think most people are so keen to judge other people?
  69. Why is it so hard for people to see things in shades of gray instead of black and white?
  70. How much does your past shape you? What parts have shaped you the most?
  71. How much do you think you improve the lives of the people around you?

For more questions like these check our philosophical questions, our deep conversation topics, or this list of conversation starters for best friends from our friends at Deeper Conversations.

Questions to ask your friends about yourself

It can be a little weird just asking someone questions about yourself, it can come off wrong. So just make sure these are the types of questions you want to be asking and if you do decide to ask these questions make sure the other person gets to choose some for themselves. 

  1. What do you think some of my favorite things are?
  2. What job do you think I’d be best at?
  3. What is my best personality trait?
  4. What did you think about me when you first met me?
  5. What do you think makes me unique?
  6. How well do you think you know me?
  7. What’s the best thing about our friendship?
  8. What do you still hold a grudge against me for?
  9. How much do you trust me?
  10. When have I let you down?
  11. How often do you think I lie to you?
  12. Which of my clothes do you think look best on me?
  13. What is my best and worst habit?
  14. What different type of aesthetic would suit me?
  15. When have I crossed one of your lines?
  16. What role do you think I play in our friend group?
  17. Would you tell me if I smelled bad?
  18. What tattoo would look good on me?
  19. What kind of vacation do you think would suit me?
  20. What hair color/style could I rock?
  21. How awkward is it for you when we sit in silence?
  22. What’s my best talent?
  23. What is you best memory of us hanging out?

You might also want to try our 21 questions game page and get your friend to ask you some of those questions.