185 Fun Questions to Ask in Absolutely Any Situation

Spark some fascinating, funny, and lively conversation with these prompts.

Science says that exchanging questions is a great way to strengthen the bond between two individuals. And while that's well and good, there's a lot more to uncover about someone beyond small talk. To get under the service, you need to ask the right questions. Below, we've rounded up some of the weirdest, most random, and most interesting conversation prompts you could ever hope to ask—or be asked—during your next encounter. Use them in good health and good spirits, and you're sure to walk away with a special new connection.

RELATED: 152 Funny Questions to Get the Whole Room Laughing.

Random Fun Questions to Ask

group of women eating ice cream on the curb and laughing
Xavier Lorenzo/Shutterstock

  1. What's your biggest pet peeve?
  2. What's your favorite sports team?
  3. What's the worst job you've ever had?
  4. What's the first thing you would buy if you were given a million dollars?
  5. What's your favorite memory from the past two weeks?
  6. Can you describe a mirror using colors?
  7. What's the weirdest thing you've ever eaten?
  8. What's the greatest invention of all time?
  9. What's one phone app you could never live without?
  10. What's one song you know all the words to without fail?
  11. Would you rather deal with a really bad sunburn or a sprained ankle?
  12. What's the best thing to re-gift?
  13. Do you believe in ghosts?
  14. What's the dumbest dance move you can think of?
  15. What's the longest car ride you've ever taken?
  16. What's one piece of technology that makes your life way easier?
  17. What do you typically wear around the house?
  18. What's the kindest thing you've ever seen someone do?
  19. Have you ever broken any bones?
  20. Is cake a normal enough thing to eat for breakfast?
  21. What's the best way to get rid of the hiccups?
  22. What's the most boring sport to watch live?
  23. What's the riskiest thing you've ever done in your life?
  24. What are three words your friends would use to describe you?
  25. Are you a morning person or more of a night owl?
  26. What was the last show you binge-watched?
  27. What's your favorite season?
  28. What's your favorite holiday?

RELATED: 210 Deep Questions to Ask for a Closer Connection.

Weird Questions to Ask Your Friends

group of co-workers thinking of fun questions to ask each other during lunch
  1. Do you have a secret talent you've been hiding from us?
  2. Where do you get fresh inspiration for creative ideas?
  3. Which fictional character would you want to marry and why?
  4. What's been your favorite age so far?
  5. Have you ever purposely swallowed toothpaste?
  6. What would you do if you found a dead body in a hotel room?
  7. What's the worst smell you can think of?
  8. What's your favorite deli meat?
  9. What's the weirdest thing you secretly do every day?
  10. If animals could talk, which species would be the nicest?
  11. What color best describes your personality?
  12. Do you ever think about how birds pee?
  13. What's the worst thing you've seen on television recently?
  14. If you had to flee the country, where would you go to find your new home?
  15. Do you have a secret hideout?
  16. If you got arrested with no prior warning, what would your friends and family assume you had done?
  17. What's the strangest text you've received in the past week?
  18. What do you typically think about when on the toilet?
  19. Who is the sixth person on your missed calls list?
  20. Where's the most random place you've ever fallen asleep?
  21. What's the dumbest thing you used to believe in?
  22. Name one celebrity you think would be genuinely kind in real life.
  23. Which meditative activity brings you the most joy?
  24. What's the strangest thing you've ever seen on the side of the road?
  25. What's the most important part of your morning routine?
  26. Can you tell us a story about the most fun you've ever had at work?
  27. What's the most interesting thing you've ever found in a thrift store?

RELATED: 180 Interesting Questions to Ask Friends You Want to Know Better.

Fun Questions to Ask Kids

father and son laying on the floor facing each other
George Rudy/Shutterstock
  1. What's your favorite movie?
  2. Who's your favorite family member?
  3. How would you survive a zombie apocalypse?
  4. What's your favorite board game?
  5. What's the funniest joke you know?
  6. Who is your favorite famous person?
  7. What's your favorite sport?
  8. How many animal sounds can you make?
  9. If you could ask your pet any question, what would you say?
  10. Would you rather go to the bottom of the ocean or into outer space?
  11. What's something you're really good at?
  12. If you could go out and buy anything right now, what would you get?
  13. What's your favorite ice cream flavor?
  14. Can you play any instruments?
  15. Have you ever eaten a bug?
  16. Do you pick your nose?
  17. What's your favorite part of the day?
  18. What is your favorite thing to put on a cracker?
  19. What's something that scares you?
  20. What's a fun way to pass the time during a long car ride?
  21. What's the funniest thing your mom or dad has ever done?
  22. What's your favorite TV show?
  23. What's the grossest food you can think of?
  24. What's your absolute favorite food to eat?

RELATED: 127 Questions to Ask Your Partner About Love, Life, & Intimacy.

Fun Questions to Ask About Someone's Past

woman looking pensive holding a pen and paper
  1. What's your favorite childhood memory?
  2. How did you meet your best friend?
  3. What was the best birthday you can remember?
  4. What's one food that always makes you think of home?
  5. Would you ever move to the same town you grew up in?
  6. What's something you do or something you own that you think might be starting to date you?
  7. What was your best-ever Halloween costume as a kid?
  8. Did you have a nickname growing up?
  9. How did you spend your summer breaks growing up?
  10. What was your favorite toy to play with as a kid?
  11. Where was the first place you drove to after getting your license?
  12. Who was your role model growing up?
  13. Did you ever cheat on a test in school?
  14. Did you keep a journal or diary when you were young? If so, do you still have it?
  15. When did you start drinking coffee?
  16. When you were little, what did you think you'd be doing at the age you are now?
  17. Were your parents strict growing up?
  18. Can you describe the craziest person you've ever met?
  19. If you could turn back time, what day would you choose to relive and why?
  20. What was your favorite subject in school?
  21. What's the most embarrassing moment you can remember from high school or college?
  22. What was the most ridiculous outfit your parents ever dressed you in?

RELATED: 200+ Get to Know You Questions That Actually Work.

Juicy Questions for R-Rated Conversations

two mature women thinking of fun questions to ask each other at a cafe
  1. What's your favorite body part?
  2. How would you describe your sex life using just one word?
  3. What's the furthest you've ever gone in a movie theater?
  4. Have you ever been in an open relationship?
  5. When did you lose your virginity?
  6. Big spoon or little spoon?
  7. Where was the last place you went skinny dipping?
  8. Have you ever had an inappropriate crush?
  9. Rough or romantic?
  10. Are you double-jointed?
  11. What's the widest age gap you've ever entertained?
  12. What's the wildest thing you've ever tried?
  13. Have you ever been caught romancing yourself? If so, by whom?
  14. Are you comfortable with laughter in the bedroom or do you prefer to keep things more serious?
  15. What was the last dirty dream you had?
  16. Have you ever accidentally sent a sexy picture to the wrong person?
  17. Do you think revealing clothes are a turn-on or a turn-off?
  18. If you had a dollar for every person you've ever kissed, what could you buy?
  19. Sleeping in the nude: yay or nay?
  20. Are you more of a giver or a reliever?
  21. What kind of music do you like to listen to when being intimate?
  22. What's your favorite way to flirt with someone?

RELATED: 206 Questions to Ask Your Crush to Learn Who They Really Are.

Creative Questions to Ask on a Date

man and woman thinking of fun questions to ask each other during a first date
  1. What's the most embarrassing thing you've ever done while trying to impress someone?
  2. How long do you wait to introduce someone to your friends?
  3. How would you describe your dream house?
  4. What's one thing you'd like to cross off your bucket list in the near future?
  5. Who is your celebrity crush?
  6. Are you a risk taker?
  7. How into podcasts are you?
  8. Do you always hit the snooze button when your alarm goes off?
  9. Do you daydream about anything in particular?
  10. What's one skill you'd love to master?
  11. How do you usually deal with conflict?
  12. Do you have any routines that you stick to religiously?
  13. Have any of your values or beliefs changed over the years?
  14. Why is pineapple on pizza so controversial?
  15. What does your ideal weekend look like?
  16. Is there any food you refuse to eat?
  17. What's something you're proud of?
  18. What's worse during a kiss: sneezing or burping?
  19. Do you believe in manifestation?
  20. What's a rule you can't help but break?
  21. What's the dumbest way you've ever injured yourself?
  22. How do you define beauty?
  23. What's your favorite international food?
  24. Have you experienced more luck on any one dating app over another?
  25. Is there one love language you gravitate toward most?
  26. What's one red flag you always look out for on a first date?
  27. Do you believe in love at first sight?
  28. What's your favorite alcoholic and non-alcoholic drink?
  29. How do you like to unwind after a long day?
  30. What's the last book you got really into?
  31. What's a good joke you've heard recently?
  32. Are you friends with any of your exes?
  33. What childhood tradition would you like to one day introduce to your own family?

RELATED: 241 Questions to Ask a Guy on a Date, In-Person, or Via Text.

Fun Questions for a More Interesting Conversation

Group of four friends laughing while hanging out outside
  1. What's the best gift you've ever been given?
  2. What's one piece of advice you'd give to your younger self?
  3. What do you consider your most prized possession?
  4. What's your most irrational fear?
  5. What are two things that seem perfectly normal, but become really strange when performed repeatedly?
  6. What's more heartwarming: a cat choosing to sit in your lap or a baby saying your name for the first time?
  7. Who knows you better than anyone else in the world?
  8. If you were the ruler of your own country, what's the first law you'd put into place?
  9. How would you feel if your partner made more money than you?
  10. Are you team Harry Potter or team Lord of the Rings?
  11. Which of these items do you find most useful: an umbrella, light bulb, cell phone, loaf of bread, or pencil?
  12. What kind of content would you create if you had your own YouTube channel?
  13. How can you tell if someone is a good listener?
  14. Which celebrity do you think does not deserve their fame?
  15. Do you have any superstitions?
  16. Have you ever farted in yoga class?
  17. Do you have any fast food horror stories?
  18. What's a telltale sign that you're upset?
  19. What's cozier: snow or rain?
  20. What's the worst thing about where you live?
  21. Do you have any recurring dreams?
  22. What's your biggest fear?
  23. Have you ever had a near-death experience?
  24. Would you rather someone be honest and hurt your feelings or lie to protect them?
  25. What superpower would you pass on?
  26. What's your least favorite mode of transportation?
  27. Would you rather have more money or more time on your hands?
  28. Who is the wrong person to call in the event of an emergency?
  29. What's the craziest thing you've ever done to get out of plans?

Wrapping Up

That's it for our list of fun questions to ask of anyone you'd like to know better, but be sure to check back in with us soon! Best Life is committed to helping you find the right words for any occasion. Sign up for our newsletter to enjoy similar kinds of content, as well as the latest in health, entertainment, and travel.

Carrie Weisman
Carrie Weisman oversees all SEO efforts at Best Life. She specializes in content optimization and editorial marketing. Read more
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