700 Random Questions to Ask Your Friends

Want to make hangouts more fun and know your friends better?

Random questions are your new best friend! From silly to serious, these questions spark conversations that you’ll remember forever. So get ready to laugh, think, and dive deep into each other’s minds. Let’s get chatting! 

Random Questions to Confuse Them

1. If you could have any superpower, but only for 10 seconds a day, what would it be?
2. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
3. If you could only eat one color of food for the rest of your life, what color would it be?
4. If you had to rename yourself using a fruit name, what would it be?
5. If animals could talk, which one would be the most annoying?
6. Is a hotdog a sandwich?
7. Would you rather have fingers as long as your legs or legs as long as your fingers?
8. If you had to pick one age to be forever, what age would you choose?
9. What would you do if you found a penguin in your freezer?
10. If you were a vegetable, what would you be?
11. Would you rather have a head the size of a watermelon or a grape?
12. What would you do if you were invisible for a day?
13. Would you rather sneeze glitter or cry chocolate tears?
14. If you had to listen to one song for the rest of your life, what would it be?
15. If you could only say one word for the rest of your life, what would it be?
16. If you could be any fictional character, who would you be?
17. Would you rather be a giant mouse or a tiny elephant?
18. If you had to smell like one food forever, what would it be?
19. What would you do if you could time travel, but only 10 seconds back or forward?
20. Would you rather have a pet dragon or be a dragon?
21. If you could have any job for just one day, what would it be?
22. Would you rather never have to sleep again or never have to eat again?
23. If you were a ghost, where would you haunt?
24. What’s something you’d never say but would like to?
25. Would you rather have one real get-out-of-jail-free card or a key that opens any door?
26. What’s your strategy for a zombie apocalypse?
27. Would you rather only be able to walk backward or only be able to hop?
28. If you could be famous for one thing, what would it be?
29. Would you rather have a rewind button or a pause button in your life?
30. If you were a pizza, what toppings would you have?
31. Would you rather always be slightly underdressed or overdressed?
32. If you could ask your future self one question, what would it be?
33. Would you rather fight a kangaroo or a badger?
34. If you were a superhero, what would your weakness be?
35. What’s your spirit animal?
36. Would you rather be able to breathe underwater or fly?
37. If you could replace one body part with a super bionic replacement, what would it be?
38. If you could be a master at any instrument but only play one song, what would it be?
39. Would you rather be able to talk to animals or speak all foreign languages?
40. Would you rather eat spaghetti with your hands or drink coffee through a straw?
41. If you had to tattoo your next text message on your body, where would you put it?
42. Would you rather live in a world with no music or no color?
43. If you could bring one fictional character to life, who would it be?
44. Would you rather live in space or under the sea?
45. If you could change one law, what would it be and why?
46. If you were a kitchen appliance, what would you be?
47. Would you rather have your dream job but always be broke or a job you hate but be filthy rich?
48. Would you rather have no sense of time or no sense of direction?
49. What would you do if you found a genie lamp?
50. Would you rather never have internet access again or never be able to travel?

Weird Random Questions

1. If you were a potato, how would you want to be cooked?
2. Would you rather fight a squirrel-sized elephant or an elephant-sized squirrel?
3. What would you do if you could control the weather for one day?
4. If you had to live in a fruit, which one would it be?
5. If you could replace your hand with any kitchen utensil, what would it be?
6. If you could only smell one scent for the rest of your life, what would it be?
7. Would you rather have a tail or an extra arm?
8. What’s the weirdest dream you’ve ever had?
9. What animal would you want to be reincarnated as?
10. What’s the strangest food you’ve ever eaten?
11. If you had to eat only one type of cheese forever, what would it be?
12. Would you rather be stuck in an elevator full of angry bees or angry snakes?
13. If you were a cereal, what would you be called?
14. If you could have dinner with any three people (real or fictional), who would they be?
15. If you were a tree, what kind would you be?
16. What’s the weirdest place you’ve ever found something you lost?
17. If your belly button had a magical power, what would it be?
18. Would you rather be an inch tall or 100 feet tall?
19. What’s the weirdest talent you have?
20. Would you rather have to eat a whole onion or a whole lemon?
21. If you could choose any animal to talk to, which one would you pick?
22. Would you rather have your mouth or your eyes glued shut for a day?
23. If you were a scent, what would you smell like?
24. What’s the strangest habit you have?
25. If you could only communicate using dance moves, would you?
26. Would you rather have spaghetti hair or sweat maple syrup?
27. If you could only eat food that rhymes with your name, what would you eat?
28. What would you do if you were the last person on Earth?
29. Would you rather be able to breathe in space or walk on lava?
30. If you could trade lives with a cartoon character, who would it be?
31. Would you rather be allergic to sunlight or allergic to smartphones?
32. What color would you want the sky to be, if not blue?
33. If you had to replace your feet with wheels, would you?
34. If you could have dinner on any planet, which one would it be?
35. What’s the weirdest gift you’ve ever received?
36. Would you rather be a human-sized ant or an ant-sized human?
37. What’s the weirdest thing you’ve ever said in your sleep?
38. Would you rather have a pet dinosaur or a pet dragon?
39. If you had to rename Earth, what would you call it?
40. What’s the most bizarre fact you know?
41. If you could eat only one food for the rest of your life, but it has no calories, what would it be?
42. Would you rather have a permanent clown face or permanent clown clothes?
43. If you could change the sound of your voice, what would it sound like?
44. Would you rather be trapped in a painting or a song?
45. What’s the weirdest YouTube video you’ve ever seen?
46. Would you rather have taste buds on your fingertips or hear through your elbows?
47. If you could turn any activity into an Olympic sport, what would it be?
48. What fictional world would you never want to visit?
49. If you could only eat things that started with the first letter of your name, what would you eat?
50. Would you rather be a reverse mermaid/merman or a reverse centaur?

Funny Random Questions

1. If you were a wrestler, what would your entrance theme song be?
2. Would you rather have a permanently clogged nose or a piece of popcorn stuck in your teeth forever?
3. What’s the silliest nickname you’ve ever had?
4. What would you do if you were invisible for one hour?
5. If you could be a professional at any board game, which one would you choose?
6. If you had to be on a reality TV show, which one would you pick?
7. Would you rather have a pet rock that could talk or a monkey that can’t?
8. If you could only wear one outfit for the rest of your life, what would it be?
9. What’s the most useless talent you have?
10. Would you rather be able to only whisper or only shout?
11. If you were a fruit, what kind would you be?
12. If you could only eat one pizza topping forever, what would it be?
13. What would you do if a penguin walked into the room right now?
14. If you were a superhero, what would your mundane, day-to-day superpower be?
15. If you could switch places with any actor in any scene of any movie, what would it be?
16. What’s the worst hairstyle you’ve ever had?
17. If you had to replace your hands with objects, what would they be?
18. What TV show do you wish your life was like?
19. What animal do you think you were in a past life?
20. Would you rather have to dance every time you hear music or sing along to any song you hear?
21. If you were a kitchen appliance, which one would you be?
22. Would you rather always be 10 minutes late or 20 minutes early?
23. What’s the funniest Wi-Fi name you’ve ever seen?
24. If you could swap your legs with the legs of any animal, which animal would you choose?
25. What food would you absolutely refuse to eat under any circumstances?
26. If you had to pick a new name for yourself, what would it be?
27. What’s the funniest joke you know?
28. Would you rather always have to skip everywhere or run everywhere?
29. If you were to win the lottery tomorrow, what are the first three things you would do?
30. What would your autobiography be called?
31. What’s the weirdest thing you’ve ever googled?
32. If you had to eat a crayon, what color would you choose?
33. If you had a pet unicorn, what would you name it?
34. Would you rather have a hand twice as big or half as small?
35. What’s the strangest thing you’ve ever eaten on a dare?
36. If you had to describe yourself as a type of bread, what would you be?
37. What’s your zombie apocalypse survival plan?
38. If you could only use one emoji for the rest of your life, which one would it be?
39. If you could instantly become an expert at any one type of dance, what would it be?
40. What’s the most ridiculous fact you know?
41. If you had to be a Disney villain for a day, who would you be?
42. What’s the most embarrassing thing that’s ever happened to you?
43. If you were a vegetable, which one would you be and why?
44. Would you rather be a chicken-sized elephant or an elephant-sized chicken?
45. What would you do if you could stop time for 10 seconds?
46. If you were a candy, what would you be?
47. What’s the funniest place you’ve ever fallen asleep?
48. What’s your go-to karaoke song?
49. If you were a flavor of ice cream, what would you be?
50. What’s the weirdest thing you’d do if you were a billionaire for a day?

About Yourself

1. What’s my middle name?
2. Can you name my favorite color?
3. What’s my go-to snack?
4. Do I prefer coffee or tea?
5. How many siblings do I have?
6. What’s my dream job?
7. What’s my favorite movie?
8. Do I like cats or dogs more?
9. What’s a hobby I love?
10. Where was I born?
11. What’s my favorite type of music?
12. What’s my zodiac sign?
13. What am I most afraid of?
14. Who’s my celebrity crush?
15. What’s my favorite food?
16. What’s my lucky number?
17. Do I prefer the beach or the mountains?
18. What’s my favorite book?
19. What’s a sport I like to watch?
20. Do I prefer summer or winter?
21. What’s my favorite TV show?
22. Am I a morning person or a night owl?
23. What’s my favorite kind of ice cream?
24. What high school did I go to?
25. What’s my favorite holiday?
26. Do I like spicy food?
27. What’s my favorite video game?
28. Who is my best friend?
29. What’s my favorite dessert?
30. Do I like to cook?
31. What’s a talent I have?
32. What’s my favorite type of exercise?
33. What’s my favorite animal?
34. What’s my favorite subject in school?
35. Do I like tattoos?
36. What’s my favorite type of weather?
37. Do I have any allergies?
38. What’s my favorite restaurant?
39. What’s my shoe size?
40. What’s my favorite social media platform?
41. What’s a place I’ve always wanted to visit?
42. What’s my favorite drink?
43. Do I play any musical instruments?
44. What’s something I always say?
45. What’s a pet peeve of mine?
46. What’s my favorite board game?
47. Am I good at keeping secrets?
48. Do I like roller coasters?
49. What’s my favorite way to relax?
50. What’s a show I’ve binge-watched recently?

About Love and Relationships

1. What’s your idea of a perfect date?
2. Do you believe in love at first sight?
3. What’s the most romantic thing you’ve ever done?
4. How did you know your partner was “the one“?
5. What’s your love language?
6. Do you think opposites attract?
7. What’s the best relationship advice you’ve ever received?
8. What’s the longest relationship you’ve been in?
9. What’s the most important thing in a relationship for you?
10. What’s a deal-breaker for you in a relationship?
11. Have you ever been in a long-distance relationship?
12. What’s your go-to love song?
13. Do you think it’s important to have common interests with your partner?
14. How do you handle arguments in a relationship?
15. What’s your favorite romantic movie?
16. How did you meet your first love?
17. What’s the most meaningful gift you’ve ever received from a partner?
18. What do you wish you knew about love when you were younger?
19. Do you think love can last forever?
20. What’s the craziest thing you’ve done for love?
21. What do you think about online dating?
22. How important is physical attraction to you?
23. What’s your ideal way to celebrate an anniversary?
24. Do you have a “type” when it comes to dating?
25. How do you know when you’re in love?
26. Do you think age matters in a relationship?
27. How do you feel about public displays of affection?
28. What’s your opinion on “love at first sight“?
29. Do you believe in soulmates?
30. What’s the most romantic place you’ve ever visited?
31. How do you keep the spark alive in a long-term relationship?
32. What qualities are most important to you in a partner?
33. How do you handle jealousy?
34. Do you believe in “the one“?
35. What’s the best way to get over a breakup?
36. How do you feel about marriage?
37. What’s your dream honeymoon destination?
38. How do you define love?
39. What’s your favorite love quote?
40. Do you think it’s okay to keep secrets in a relationship?
41. How important is money in a relationship for you?
42. What’s your ideal proposal story?
43. What’s your opinion on open relationships?
44. How important is family approval in a relationship for you?
45. Do you have a relationship role model?
46. What do you think about “taking a break” in a relationship?
47. What’s the best way to say “I love you” for the first time?
48. How do you feel about dating a friend’s ex?
49. What do you think is the right time to move in together?
50. How do you keep boundaries in a relationship?

About Movies and TV Shows

1. What’s the last movie you watched?
2. What’s your all-time favorite TV show?
3. Who’s your favorite actor or actress?
4. What’s your favorite movie genre?
5. Can you name a movie that made you cry?
6. What’s the funniest movie you’ve ever seen?
7. Do you like watching foreign films?
8. What’s a movie you think is overrated?
9. What TV show are you watching right now?
10. Do you prefer comedy shows or drama shows?
11. What’s the scariest movie you’ve ever seen?
12. Who’s your favorite superhero in movies or TV?
13. Have you ever binge-watched a TV show in one day?
14. What’s a classic movie you’ve never seen but want to?
15. Do you like musicals? If so, which one is your favorite?
16. What’s the most epic movie you’ve ever seen?
17. What’s a movie you love that most people haven’t heard of?
18. Have you ever walked out of a movie because it was bad?
19. Do you prefer watching movies in the theater or at home?
20. What’s your favorite movie quote?
21. What’s a show you loved as a kid?
22. Who’s your favorite TV show character?
23. Do you watch reality TV?
24. What’s a movie that you think deserves a sequel?
25. Who’s the best movie villain?
26. What’s your favorite animated movie?
27. Have you ever watched a TV show just because someone recommended it?
28. What’s a movie that always makes you laugh?
29. Do you like documentaries? If so, what’s a good one you’ve seen?
30. What’s a movie you can watch over and over again?
31. Do you like watching sports movies?
32. What’s your favorite movie soundtrack?
33. Have you ever dressed up as a movie or TV character for Halloween?
34. What’s your favorite TV show theme song?
35. What movie would you like to see turned into a TV show?
36. Do you have a favorite film director?
37. What’s the first movie you remember seeing in theaters?
38. Do you like watching movie adaptations of books?
39. What’s a TV show you thought you’d hate but ended up loving?
40. What’s the best action movie you’ve seen?
41. Do you like romantic comedies?
42. What’s your favorite movie from the year you were born?
43. Have you ever watched a TV series more than once?
44. What’s a TV show that you think ended too soon?
45. Do you like watching award shows like the Oscars?
46. What’s a movie that changed your life?
47. Do you prefer old movies or new movies?
48. What’s a show that everyone loves but you don’t get the hype?
49. What’s your favorite movie based on a true story?
50. Do you like movie sequels and prequels?

About Food and Cooking

1. What’s your favorite comfort food?
2. Do you like cooking or eating out more?
3. What’s the best dish you know how to cook?
4. What’s a food you can’t stand?
5. Do you have any food allergies?
6. What’s your favorite fast-food place?
7. What’s your go-to breakfast?
8. What’s your favorite fruit?
9. Do you like seafood?
10. What’s your favorite kind of pizza?
11. Have you ever tried making your own bread?
12. Do you like sweet or savory snacks?
13. What’s the weirdest food you’ve ever eaten?
14. Do you follow any food blogs or YouTubers?
15. Do you like spicy foods?
16. What’s a dish you’d love to learn how to make?
17. What’s your favorite kind of cheese?
18. Do you have a signature dish?
19. What’s your favorite international cuisine?
20. What’s the most complicated dish you’ve ever cooked?
21. What’s your favorite thing to grill?
22. Do you prefer soda or juice?
23. What’s your favorite ice cream flavor?
24. What’s the best cake you’ve ever had?
25. Do you like eating veggies?
26. Do you use cookbooks?
27. Have you ever taken a cooking class?
28. What’s your favorite cookie?
29. What’s your favorite kind of salad?
30. What’s your go-to midnight snack?
31. Do you like smoothies?
32. What’s the first dish you ever cooked?
33. Do you prefer burgers or hot dogs?
34. What’s your favorite holiday food?
35. What’s your go-to potluck dish?
36. Do you like eating breakfast for dinner?
37. What’s your favorite candy?
38. Do you prefer tea or coffee?
39. What’s your favorite sandwich?
40. Have you ever been to a food festival?
41. Do you like trying new foods?
42. What’s your favorite dip?
43. Do you prefer homemade meals or takeout?
44. What’s a dessert you don’t like?
45. What’s your favorite kind of soup?
46. Do you like meal prepping?
47. Have you ever done a food challenge?
48. What’s your go-to drink at a coffee shop?
49. What’s your favorite type of bread?
50. Have you ever cooked a meal for more than 10 people?

About Music and Bands

1. What’s the last song you listened to?
2. Who’s your favorite artist or band?
3. What’s your go-to karaoke song?
4. What’s the best concert you’ve ever been to?
5. Do you play any musical instruments?
6. What’s a song that makes you happy?
7. What’s your favorite genre of music?
8. Have you ever met a musician you admire?
9. What’s a song you can’t stop singing along to?
10. What’s the first album you ever bought?
11. Do you like going to music festivals?
12. What’s a song you love from the year you were born?
13. Do you have a favorite music video?
14. Do you listen to podcasts about music?
15. What’s a song that makes you want to dance?
16. Who’s an underrated artist you think people should listen to?
17. What’s a band you loved as a teenager?
18. Do you like listening to live music?
19. What’s the most emotional song you’ve ever heard?
20. Do you like to listen to music when you work out?
21. What’s a song that helps you relax?
22. Do you prefer digital music or vinyl records?
23. What’s a popular song that you don’t like?
24. Have you ever been in a band or choir?
25. What’s your favorite song to listen to on a road trip?
26. Do you have a favorite movie soundtrack?
27. What’s a song that reminds you of your childhood?
28. What’s your favorite workout playlist?
29. Do you like to discover new music or stick to your favorites?
30. What’s a song that you love but is totally different from what you usually listen to?
31. What’s your favorite song lyric?
32. Have you ever written a song?
33. Do you like listening to covers of songs?
34. What’s the first concert you ever went to?
35. Do you have a favorite one-hit wonder?
36. What’s a song that reminds you of someone special?
37. What’s the best album you’ve listened to recently?
38. Do you have any guilty pleasure songs?
39. Do you like classical music?
40. What’s your go-to shower song?
41. Do you listen to music when you’re feeling down?
42. Who’s an artist you used to love but don’t listen to anymore?
43. What’s your favorite duet?
44. Have you ever made a mixtape or playlist for someone?
45. What’s a band you wish would get back together?
46. Do you have a favorite Christmas song?
47. Who’s an artist you want to see live but haven’t yet?
48. What’s your favorite song to listen to in the morning?
49. Do you have a favorite song from a musical?
50. What’s a song that always gets stuck in your head?

About Travel and Adventure

1. What’s the last place you traveled to?
2. What’s your dream vacation spot?
3. Have you ever traveled solo?
4. Do you prefer the beach or the mountains?
5. What’s the longest flight you’ve been on?
6. Do you like road trips?
7. What’s your favorite city that you’ve visited?
8. Have you ever been camping?
9. Do you like to stay in hotels or Airbnb?
10. What’s the most exotic food you’ve tried while traveling?
11. Do you collect souvenirs from places you visit?
12. What’s your go-to travel snack?
13. Have you ever gotten lost while traveling?
14. What’s the coolest landmark you’ve ever visited?
15. Do you like to visit museums when you travel?
16. What’s the most beautiful place you’ve ever been to?
17. Do you prefer traveling with family or friends?
18. What’s a place you’d never want to visit?
19. Have you ever been on a cruise?
20. What’s the most adventurous thing you’ve done while traveling?
21. Do you like to plan your trips or be spontaneous?
22. What’s your favorite travel app?
23. Have you ever been to a theme park in another country?
24. Do you prefer the city or the countryside when traveling?
25. What’s your favorite way to pass time on a long journey?
26. What’s your must-have travel item?
27. Do you prefer hot places or cold places?
28. Have you ever visited a place that felt like home?
29. What’s a country you want to visit but haven’t yet?
30. What’s the first trip you remember taking?
31. Do you like taking pictures when you travel?
32. What’s your favorite travel memory?
33. Have you ever traveled for a special event like a wedding or festival?
34. Do you like to try local foods when you travel?
35. What’s the most relaxing vacation you’ve ever had?
36. Have you ever had a trip go totally wrong?
37. Do you like to travel light or pack a lot?
38. Have you ever stayed in a hostel?
39. What’s the most remote place you’ve visited?
40. Have you ever visited a place just because you saw it in a movie or on TV?
41. Do you like history tours or nature hikes?
42. What’s your dream travel destination for a honeymoon?
43. What’s a local dish you fell in love with while traveling?
44. Have you ever gone backpacking?
45. What’s the furthest you’ve traveled from home?
46. Have you ever been on a safari?
47. Do you like to travel during the holidays?
48. What’s your favorite way to meet new people while traveling?
49. Do you ever travel for work?
50. What’s on your travel bucket list?

About Fun Hypotheticals

1. If you could have any superpower, what would it be?
2. If you could time travel, where and when would you go?
3. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
4. If you won the lottery, what’s the first thing you’d buy?
5. If you could be any animal for a day, which one would you choose?
6. If you could have dinner with any three people, dead or alive, who would they be?
7. Would you rather be famous or the best friend of someone famous?
8. What fictional world would you love to live in?
9. If you could swap lives with any historical figure, who would it be?
10. Would you rather always be 10 minutes late or always be 20 minutes early?
11. If you were invisible for a day, what would you do?
12. What’s a talent you wish you had?
13. If you could be the best in the world at one thing, what would it be?
14. Would you rather never eat your favorite food again or only eat your favorite food?
15. If you could relive any day of your life, which one would you choose?
16. If you could talk to animals, what’s the first thing you’d ask them?
17. Would you rather be able to fly or breathe underwater?
18. If you had to eat only one cuisine for the rest of your life, what would it be?
19. What’s a law you would make if you were president for a day?
20. Would you rather always have to sing rather than speak or dance everywhere you go?
21. If you could change one thing about your past, what would it be?
22. What’s a movie you wish you could live in?
23. If you could be any age for a week, what age would you choose?
24. Would you rather be super smart or super strong?
25. If you could instantly learn any language, which one would it be?
26. What’s a job you would love to try for a day?
27. If you were a ghost, who or where would you haunt?
28. Would you rather never have to sleep again or never have to eat again?
29. If you could choose your own nickname, what would it be?
30. What’s a skill you’d like to master instantly?
31. If you could teleport, where’s the first place you’d go?
32. Would you rather lose all your money or all your pictures?
33. If you could have any pet in the world, real or fictional, what would you choose?
34. Would you rather always have to say what you’re thinking or never be able to speak again?
35. If you could make one rule that everyone had to follow, what would it be?
36. Would you rather be able to talk to your past self or your future self?
37. What’s a game or sport you wish you were pro at?
38. If you had a magic wand, what’s the first thing you’d do?
39. What’s an invention you wish existed?
40. Would you rather live without music or without TV?
41. If you could be a character in any book, who would you be?
42. Would you rather live in space or under the sea?
43. If you could erase one thing from existence, what would it be?
44. What’s a TV show you wish never ended?
45. Would you rather live without the internet or without air conditioning?
46. What’s a hobby you’d take up if time and money weren’t an issue?
47. If you had a time machine, would you go to the future or the past?
48. Would you rather be incredibly lucky or incredibly skilled?
49. What’s a question you’ve always wanted to know the answer to?
50. If you were a superhero, what would your superhero name be?

About Hobbies and Interests

1. What’s a hobby you’ve always wanted to pick up but never did?
2. Do you have a hidden talent?
3. What’s your favorite way to relax after a long day?
4. Are you into any extreme sports?
5. Do you like painting or drawing?
6. What’s your go-to video game?
7. Do you like doing puzzles?
8. Are you a morning person or a night owl?
9. Do you play any board games?
10. What’s your favorite thing to do at the beach?
11. Do you like gardening?
12. What’s a book you couldn’t put down?
13. Do you like to write?
14. Are you into astrology?
15. What’s your favorite type of dance?
16. Do you collect anything?
17. Do you like to go fishing?
18. What’s your favorite way to exercise?
19. Are you into DIY projects?
20. Do you enjoy cooking for others?
21. What’s a sport you’re really good at?
22. Do you like birdwatching?
23. What’s your favorite thing to photograph?
24. Do you like to go thrift shopping?
25. Are you a fan of hiking?
26. Do you enjoy stargazing?
27. Have you ever tried geocaching?
28. Do you like scrapbooking?
29. What’s your favorite social media platform?
30. Are you into podcasts?
31. Do you like magic tricks?
32. Are you into fashion?
33. Do you enjoy knitting or crocheting?
34. What’s your favorite card game?
35. Do you play any musical instruments?
36. Are you into stand-up comedy?
37. Do you like attending live sports events?
38. What’s a movie you can watch over and over?
39. Do you like to bake?
40. Are you into meditation?
41. Do you enjoy roller coasters?
42. What’s your favorite way to spend a rainy day?
43. Do you like going to the zoo?
44. Are you a history buff?
45. Do you enjoy cycling?
46. Do you like to go camping?
47. What’s your favorite kind of puzzle?
48. Do you enjoy doing karaoke?
49. Are you into martial arts?
50. Do you like making your own jewelry?

About Childhood

1. What’s your earliest memory?
2. Did you have a favorite stuffed animal?
3. What was your go-to childhood snack?
4. Who was your best friend in kindergarten?
5. Did you play any sports as a kid?
6. What was your favorite subject in school?
7. Were you a troublemaker or a goody-two-shoes?
8. What’s a childhood game you loved to play?
9. Did you have any silly fears as a kid?
10. What’s a TV show you were obsessed with?
11. What was your favorite book as a kid?
12. Did you ever go to summer camp?
13. What’s a toy you always wanted but never got?
14. What’s the first movie you remember seeing in theaters?
15. Did you have any childhood heroes?
16. What was your favorite playground equipment?
17. What was your favorite candy?
18. What was your favorite birthday party?
19. Were you in any clubs in school?
20. Did you ever have a treehouse or fort?
21. Did you like family road trips?
22. What’s the first thing you saved your allowance for?
23. Did you believe in Santa Claus?
24. Were you a picky eater?
25. Did you have a childhood nickname?
26. What was your favorite thing to wear as a kid?
27. What’s the worst trouble you got into?
28. What’s the first song you remember loving?
29. Were you into video games?
30. What’s your favorite family tradition from your childhood?
31. Did you have a favorite cartoon character?
32. What’s something you miss from your childhood?
33. What was your first pet’s name?
34. What was your favorite family vacation?
35. Did you ever win any trophies or medals as a kid?
36. What’s a talent show act you did?
37. Did you collect anything?
38. What’s a childhood habit you still have?
39. What’s a weird food you loved as a kid?
40. Did you ever have an imaginary friend?
41. What’s a lesson you learned the hard way as a kid?
42. What was your go-to Saturday morning cartoon?
43. Did you ever make a prank call?
44. What was your favorite cereal?
45. Did you ever have a lemonade stand?
46. What’s a funny childhood story your family always tells?
47. Were you good at hide and seek?
48. Did you have a favorite relative you loved to visit?
49. What was your favorite holiday as a kid?
50. Did you ever have to go to the principal’s office?

About Work and School

1. What was your first job ever?
2. Did you have a favorite teacher in high school?
3. What’s the most interesting project you’ve worked on?
4. Have you ever pulled an all-nighter for school or work?
5. What was your favorite field trip as a kid?
6. What’s the most boring job you’ve ever had?
7. Did you join any clubs in high school or college?
8. What was your favorite lunch to bring to school?
9. Have you ever had a really tough boss?
10. Did you like gym class?
11. What’s the most useful thing you’ve learned in your current job?
12. Did you ever cheat on a test?
13. What’s your go-to work outfit?
14. What subject did you struggle with the most?
15. Have you ever gotten a promotion?
16. What’s your dream job?
17. Have you ever been fired?
18. What’s the best career advice you’ve received?
19. Did you go to prom?
20. Do you prefer working from home or in the office?
21. What was your major in college?
22. Have you ever had a work crush?
23. Did you take any fun electives in school?
24. What’s the hardest part about your job?
25. What’s the best school project you’ve ever done?
26. Have you ever been the “employee of the month“?
27. What was your least favorite job and why?
28. Did you ever skip class?
29. What’s the coolest work event you’ve been to?
30. Have you ever done any internships?
31. Did you ever forget your lunch at home?
32. What’s the longest you’ve ever stayed at a job?
33. Did you ever win any academic awards?
34. Have you ever had to work on a holiday?
35. Did you have a study group in college?
36. What’s the most difficult decision you’ve had to make at work?
37. Did you ever get caught passing notes in class?
38. What’s the best perk about your job?
39. Did you ever take a gap year?
40. Have you ever had to do a presentation at work?
41. What’s a subject you wish you’d paid more attention to?
42. Have you ever had a side hustle?
43. Did you ever have to wear a uniform to school?
44. What’s the most challenging job you’ve ever had?
45. What’s your favorite school or work memory?
46. Do you get along with your coworkers?
47. Did you play any sports in school?
48. Have you ever led a team at work?
49. What was your go-to snack during study sessions?
50. Have you ever had a really easy job?

About Family and Home Life

1. What’s your favorite home-cooked meal?
2. Do you have any family traditions?
3. Did you share a room growing up?
4. What’s your favorite room in your house?
5. Do you have any siblings?
6. What’s the best piece of advice your parents ever gave you?
7. Did you have family game nights?
8. What’s your idea of a perfect weekend at home?
9. Did you go on family vacations?
10. Do you have a “family movie” that everyone loves?
11. Do you have any family inside jokes?
12. What’s the biggest family gathering you’ve been to?
13. What’s your favorite family holiday?
14. How did your parents meet?
15. Do you enjoy DIY home projects?
16. Are you close with your extended family?
17. What’s a family recipe you love?
18. What chores did you hate the most as a kid?
19. What’s the first big purchase you made for your home?
20. Do you have any family heirlooms?
21. Who’s the funniest person in your family?
22. What’s your favorite childhood memory with your family?
23. Do you like having guests over?
24. How do you deal with family disagreements?
25. What’s the best gift you’ve ever given your parents?
26. What’s your go-to comfort food at home?
27. Did your family have a pet when you were growing up?
28. What’s your family’s favorite takeout?
29. Do you have a favorite family photo?
30. Did your family ever have a garage sale?
31. Who’s the most organized person in your family?
32. Did your family have any weird rules?
33. What’s your favorite type of family outing?
34. Have you ever traced your family history?
35. Who in your family are you most like?
36. Do you like hosting family events?
37. What’s a lesson your family taught you?
38. Have you ever moved houses?
39. What’s a special talent someone in your family has?
40. Do you have a favorite aunt or uncle?
41. What’s the furthest you’ve been from home?
42. Have you ever had a big family reunion?
43. Who’s the best cook in your family?
44. What’s a typical Sunday like at your home?
45. What’s the oldest thing in your home?
46. Do you have any family friends you’ve known forever?
47. What’s a favorite story from your grandparents?
48. Do you have a family sport?
49. What’s a home improvement you’d like to make?
50. How do you celebrate birthdays in your family?

Frequently Asked Questions

How do I keep the conversation flowing?

• Listen Carefully: Sometimes, the answers to one question can spark a whole new question.
• Be Open: Share your own thoughts and feelings as well.
• Mind the Mood: If a question brings down the mood, have a lighter one ready to lift spirits again.

Can I ask these questions in a group setting?

Yes, and that can actually make it even more fun. Different perspectives can make the conversation more enriching. However, be mindful that some people may be more comfortable answering certain questions in a one-on-one setting.