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Random Questions to Ask

Looking for random questions to ask someone to start a conversation? People love to talk – among various things, they love to talk about themselves. While some people love to talk with much enthusiasm, others might need a push or a stimulus. That’s where ice-breaking questions can come useful when starting a conversation. A good conversation can thrive when the participants ask each other excellent questions.

Therefore, we have compiled a list of random questions to ask to get to know anyone you want!

Random questions to ask
Random questions to ask

Best random questions to ask

  1. What’s the most ridiculous thing you’ve been duped into doing by your friends?
  2. What is one truth about you that no one believes?
  3. How difficult would it be if you had married a vegan?
  4. If you were exiled from the country, where would you go?
  5. Who is one person whom you would like to avoid in your life?
  6. Who is cooler – your dad or mom?
  7. What is one incident when your sibling tricked you?
  8. When was the last time you were outsmarted by a person you thought was dumb?
  9. What was the worst April fool you had in your life?
  10. Do you love vintage cars or modern cars?
  11. Have you ever gone to prison?
  12. What is the most bizarre food you have ever tasted?
  13. What’s an unusual habit that very few people know about you?
  14. What would be your first decision if you were ever made the President of the USA?
  15. Do you like fishing or boating?
  16. If you are paid for bad behavior, what behavior of yours can make you a fortune?
  17. If you had to be an expert conman in a profession, which profession would you choose?
  18. Which job do you think is the most undermined and underpaid?
  19. If you could domesticate a wild animal, which one would it be?
  20. How much money would you charge if you were to swallow a dead worm?

Expert advice: Clinical psychologists frequently refer to this study. It shows that laughter truly is a “medicine.” When meeting new people, getting a laugh from them won’t simply make them appreciate you. It may improve their health, too.

Random questions to ask
Random questions to ask

Random questions to ask to start a conversation

  1. How was your first date?
  2. How do you react when people call you but forget the reason?
  3. What is one strange coincidence that has ever happened to you?
  4. If you have to eat only one food next five years, what would that be?
  5. What is one thing people would never guess about you?
  6. What is a story you love to tell but hardly ever get a chance to?
  7. What is one popular but negative opinion people have about you?
  8. What sport will you like to invent next?
  9. What was the most memorable memory of your high school?
  10. What is one unusual item you keep in your refrigerator?
  11. If you had to wish for one last thing in your life, what would it be?
  12. Have you ever sneaked into your girlfriend/boyfriend’s house in the night?
  13. Have you ever broken the law but didn’t get caught?
  14. What was the most bizarre thing you ever did in your childhood?
  15. If you had to travel time, which era would you live in?

Related: Random questions to ask a girl

Random questions to ask
Random questions to ask

To ask your friends

—Random questions to ask your friends

  1. What makes you feel jealous of me?
  2. What do you choose between your heart and your mind?
  3. What was the most eye-opening moment for you in life?
  4. What is one thing you want to change about your past?
  5. What would it be if you had to choose only one between beauty, power, and money?
  6. Do you think you have achieved what you always wanted to achieve in life?
  7. If you could change a regretful moment, what would it be?
  8. What do you think about people – they are mostly good or evil?
  9. What is one thing that you love about traveling?
  10. What philosophy do you follow in your life?
  11. What was one experience that changed your life?
  12. What is one thing for which you hate yourself?
  13. What deja vu moment do you remember well?
  14. What legacy do you like to leave behind after you are gone?
  15. What gives you hope in the most difficult times?

Related: Random questions to ask a guy

Random questions to ask
Random questions to ask

For a girl

—Random questions to ask a girl

  1. Who is your celebrity crush?
  2. Do you like to read a book or take a nap when you travel?
  3. What’s one thing for which you can go to any extent?
  4. What do you do when you are agitated?
  5. What’s the scariest dream you’ve ever had?
  6. How do you react when you make a mistake?
  7. What is one thing that you find strangely attractive in boys?
  8. If you could read the mind of a celebrity, who would it be?
  9. What is one thing people meeting you the first time wrongly assume about you?
  10. If you could steal a thing from your friend, what it be and from whom?
  11. Did you dial the wrong number but find the person interesting?
  12. What is the strangest way someone has asked for a date?
  13. If you had to invite only three people to your wedding, who would they be?
  14. If you had to travel solo to a place, where would it be?
  15. Who would you choose to go on a date with – Brad Pitt, Tom Crusie, or Leonardo DiCaprio?

To ask your girlfriend

—Random questions to ask your girlfriend

  1. What is one thing others find fun but you don’t?
  2. What is the most thoughtful gift you like to receive?
  3. Which is one place you want to visit anyhow in your lifetime?
  4. What is your favorite TV show?
  5. Which food do you like more – Italian or Mexican?
  6. Would you rather join a gym or a Yoga session?
  7. What is one thing that makes you upset the most?
  8. If you had to choose only one ice cream flavor every time you want to have it, which one it would be?
  9. What is one question you always wanted to ask me but could not dare?
  10. When do you pretend to be annoyed but secretly love it?
  11. What is one thing that you want to steal from your favorite celebrity crush?
  12. What is your favorite vacation country?
  13. What makes you annoyed on Instagram?
  14. If you could check my phone, what would you check first?
  15. Do you feel proud or jealous when other girls publicly check me out?

Questions to ask people

—Random questions to ask people

  1. What are your views on life?
  2. Do you like to have a simple life or an extravagant life?
  3. What’s one thing about yourself that you’d like to change?
  4. When was the last time you had a binge night?
  5. Who is your all-time favorite president?
  6. Do you consider yourself a trustworthy person?
  7. What is one silly thing you are passionate about?
  8. If you could enter the White House invisibly, what would you do?
  9. What makes you believe people you don’t know?
  10. What is one talent you wish you never had?
  11. Which was the best trip you ever had in your life?
  12. If you had magical power for a day, how do you use it?
  13. Do you like to have a cat or a dog as a pet?
  14. How did you meet your first crush?
  15. Would you like to be in a job that you are not passionate about but pays well, or can you settle for less if you find a job you’re passionate about?

Fun random questions to ask

  1. What’s the most ticklish spot on your body?
  2. What is something that characters do in movies that annoys you the most?
  3. What is the most ridiculous outfit you have ever worn in public?
  4. If you could speak to one animal, which one it would be?
  5. What is the most creative Wi-Fi password you ever know?
  6. Which animal would be the rudest if it could speak?
  7. If you could extend the period of one season, which one would it be?
  8. How comfortable would you be if you have to show your closet right now?
  9. What is the greatest risk you have ever taken for your crush?
  10. Which is one book you can read again and again?
  11. Would you rather leave Facebook or Instagram?
  12. What place would you first travel to if you could teleport?
  13. What sitcom scenario would you most like to see play out in real life?
  14. If you had to invest $1 million in one stock, which one would it be?
  15. Which movie villain would like to be your roommate?

Random questions to ask your crush

  1. What similarity do you find between you and me?
  2. What is your worst cooking experience?
  3. What does your ideal weekend look like?
  4. What’s your favorite pastime?
  5. What’s your favorite way to indulge?
  6. Do you like planning in advance or love to be spontaneous?
  7. What is your superstition (if you believe in it)?
  8. What movie best describes your life?
  9. What song can you listen to in a loop without getting tired of it?
  10. Who was your first crush/love?
  11. What is one childhood memory that you are ashamed of?
  12. Did you ever feel heartbroken?
  13. Do you have any phobias that you never share with anyone?
  14. How do you deal with stress or anxiety?
  15. What traits do you think are most important to find in a partner?

Funny random questions to ask

  1. Which weird animal would you be willing to take on as a pet?
  2. What is the best business idea you have ever had?
  3. What is one thing for which you like yourself?
  4. Would you like to visit a place where you can’t communicate with anyone?
  5. What is one unforgettable goosebumps moment in life?
  6. What will you do first if you ever wake up to find your gender changed?
  7. What is one food that you can’t live without?
  8. Who is one person always on your speed dial?
  9. What is one weird thing you can’t stop doing in public?
  10. How would you react if you had ever been kidnapped by aliens?
  11. What is one thing you want to be famous for?
  12. What is the most ridiculous thing you ever did on a date?
  13. How do you react when you realize you forgot to switch on the charger after an hour?
  14. Would you rather go to a mountain or beach for a holiday?
  15. What was the most unexpected and coolest punishment you ever got?

Weird random questions to ask

  1. Did you ever wave at someone thinking you know the person, only to realize that it is not the person?
  2. What is one song you pretend to dislike but you enjoy secretly?
  3. Have you ever tried to look cool in front of someone and failed?
  4. What’s the weirdest thing you have done on public transport?
  5. Have you ever slept in class and woken up only to find everyone else staring at you?
  6. If you could live anywhere in the world but had to stay naked all the time, where would you choose? 
  7. Have you tried a voice accent impersonation only to fail miserably?
  8. Did you ever fall in front of a large crowd?
  9. What’s one weirdest fact you know about your sibling?
  10. Did you ever blackmail your best friend/sibling after finding their weirdest fact?
  11. Did you ever wake up in the morning only to find that you have more time to sleep?
  12. What would it be if you were given the to speak your mind in front of your boss?
  13. What is classy, according to you, that others consider trashy?
  14. If animals can speak, who do you think will be the most sarcastic?
  15. What’s the most awkward first date you’ve ever been on?
  16. Have you ever yelled at a person only to realize later that you yelled at the wrong person?
  17. What can be the dumbest bio to write for a dating app?
  18. What is the one useless talent you have that you are ashamed of?
  19. What would you do if you were given a useless superpower?
  20. What is the dumbest way to injure yourself?

Random questions to ask over text

  1. What are your favorite “go-to” videos or screenshots for a laugh?
  2. What was the most embarrassing thing you ever said to someone?
  3. What is the most amusing thing you ever received on your birthday?
  4. What’s your favorite quote from a movie?
  5. What’s the funniest text you have ever received?
  6. What was the weirdest thing that you faced last week?
  7. Why would you go mad while driving?
  8. What was the worst text you accidentally sent to someone?
  9. Which item do you really wish to buy right now?
  10. If you had to buy only one thing on Black Friday Sale, what would it be?
  11. Do you find it funny when people share a secret that you already know?
  12. What was one incident from your childhood you want to forget but can’t?
  13. What strange smell do you find surprisingly appealing?
  14. What are some unwritten rules you follow in life?
  15. What is a thing that is not real but you want it to be?

Random questions to ask a stranger

  1. Did you ever apologize to someone for no reason?
  2. What is a rumor about you wish it to be true?
  3. If you had to start a conspiracy, what would it be?
  4. What is one thing that is invisible but you wish to see it?
  5. Which sound do you think would be the scariest if people could hear it?
  6. What is the scariest dream you ever had in your life?
  7. What is one dream you have that you wish to be true?
  8. What is the last movie you watched in the theater you think was a waste of time?
  9. What would you do if you were trapped on an island with a beautiful girl?
  10. When was the last you were upset after watching your favorite lose?
  11. If you go back to one past year, which one would it be?
  12. What is the weirdest place you visited on vacation?
  13. What is a stupid thing you stole from someone?
  14. Would you be comfortable showing your Google search history, including the Incognito history if you could?
  15. Which is your favorite social media app?

Random questions to ask when you’re bored

  1. If you could go on a date with an animal or bird, which one it would be?
  2. What was the most embarrassing moment in your grade school?
  3. Have you tried to impress someone only to fail terribly?
  4. What makes you feel proud when you are in public?
  5. If you had to give up one piece of electronics in life, what would it be?
  6. Did you ever give someone advice that proved to be ridiculous?
  7. Did you ever laugh out loud in public?
  8. When was the last time you shouted at yourself for your stupidity?
  9. If you could change the result of one FIFA final, which one would it be?
  10. What is one bad habit you want to get rid of badly?
  11. If you could dive deep into the ocean for a day, what would you do?
  12. Did you ever visit a therapist because you find him/her attractive?
  13. What is your favorite guilty pleasure?
  14. If you have to leave your office early, what reason would you tell your boss?
  15. Did you ever watch cartoons with kids and find them enjoyable?

Interesting questions to ask

  1. What’s your favorite sleeping position?
  2. Which three scents do you like the most?
  3. What’s one thought you ever had that you think is the weirdest?
  4. What comes to your mind when you hear the word “Chinese”?
  5. What’s one letter you would like to erase from the English alphabet?
  6. What animal or bird would you like to be reincarnated as?
  7. If you were given a chance to visit a planet in the solar system apart from the Earth, which one would it be?
  8. Are you a Marvel fan or a DC fan?
  9. If you could become a Marvel character for a day, which one would it be?
  10. What would you do if you were given the power of your favorite Marvel character?
  11. How will you react when you realize that you have become invisible?
  12. Which place on Earth does fascinate you the most?
  13. What’s one thing without which you can’t live?
  14. What’s your favorite foreign language?
  15. Which song reminds you of your childhood?

Teenage random questions to ask

  1. What’s the most irritating thing that friends do to you?
  2. What’s your favorite exotic cuisine?
  3. What would like to learn if you have to – French or Spanish?
  4. How many of your classmates share the same first name as you?
  5. What color would you choose to paint your bedroom?
  6. What do you like more for your birthday – Ice cream cake or sponge cake?
  7. If you have to become the principal of your school, what would you like to change?
  8. What comes to your mind when you are alone and it becomes dark?
  9. Where will you go if you could travel anywhere in the world for free right now?
  10. What’s your favorite soda flavor?
  11. If you have to choose between wealth and fame, what would you choose?
  12. Who is your celebrity crush that no one knows?
  13. Has your teacher ever caught you sleeping in class?
  14. Who is your favorite sports celebrity?
  15. Who can you approach easily when you make a mistake – your dad or mom?

Basic random questions to ask (conversation starters)

  1. Which famous person would you like to have dinner with and why?
  2. What’s the strangest thing you do when no one is looking?
  3. What did your past relationship teach you about love?
  4. What’s one word that best describes who you are?
  5. If you could go anywhere in the entire world, where would it be?
  6. What’s your most useless talent?
  7. What’s your favorite sports team?
  8. How many pairs of sneakers do you own?
  9. How would you describe humanity to an alien?
  10. Do you have a secret talent?
  11. What’s your favorite family tradition?
  12. What’s your favorite fast food restaurant?
  13. What is your favorite movie of all time?
  14. What’s the craziest thing you’ve ever done with your friends?
  15. What’s the funniest thing to ever happen to you?

Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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