950 Questions to Ask Your Crush [Never Run Out]

Want to get closer to your crush but don’t know what to say? Asking questions is the golden key! It’s like a fun game where you both win. You learn cool stuff about them, and they get to know you too.

From silly to serious, questions help turn small talk into a real chat. So get ready because asking the right questions can light that romantic spark!

Flirty Questions to Ask

  1. What’s your idea of a perfect date with me?
  2. How would you feel about a midnight kiss?
  3. Do you believe in love at first sight, or should I walk by again?
  4. What’s your favorite thing to daydream about?
  5. What’s the most romantic movie you’ve ever seen?
  6. How would you react if I kissed you right now?
  7. What kind of outfit would you like to see me in?
  8. What’s your favorite pick-up line?
  9. What’s the most daring thing you’ve ever done?
  10. Do you think we have chemistry?
  11. How would you feel if we went on a beach vacation together?
  12. What’s your go-to dance move?
  13. Do you like cuddling, or are you more of a space person?
  14. What’s your idea of the perfect kiss?
  15. What’s the most romantic place you’ve ever been to?
  16. How do you like to be kissed?
  17. What’s your biggest turn-on?
  18. What’s your favorite love song?
  19. Do you like it when someone makes the first move?
  20. What’s your favorite type of hug?
  21. Do you think you’re a good kisser?
  22. Would you rather go out for a fancy dinner or have a cozy night in?
  23. How would you feel about a weekend getaway with me?
  24. What’s your favorite thing about flirting?
  25. How do you feel about PDA (public displays of affection)?
  26. What’s the sexiest quality someone can have?
  27. What’s your zodiac sign, and do you think we’re compatible?
  28. What’s your go-to drink on a night out?
  29. Do you like it when a girl/guy plays hard to get?
  30. How would you feel about skinny dipping?
  31. What’s the most romantic thing you’ve ever done?
  32. Do you like to be the big spoon or the little spoon?
  33. How do you feel about breakfast in bed?
  34. What’s your favorite feature of mine?
  35. Do you believe in love languages, and what’s yours?
  36. What’s your favorite thing to do on a rainy day?
  37. Would you ever write a love poem?
  38. What’s the most exciting date you can think of?
  39. What’s a secret talent that makes you extra dateable?
  40. What’s your idea of a dream vacation?
  41. How would you feel about a couples’ massage?
  42. What’s your favorite dessert, and would you share it with me?
  43. Do you prefer holding hands or linking arms?
  44. How would you feel about a couples’ cooking class?
  45. Do you like to be surprised, or do you like to call the shots?
  46. What’s the most spontaneous thing you’ve ever done?
  47. Would you ever take dance lessons with me?
  48. What’s a pet name you’d give me?
  49. Do you like it when I text you first?
  50. How would you feel if I serenaded you?

Funny Questions to Ask

  1. If you could have any superpower but only one, what would it be?
  2. If you were a vegetable, what vegetable would you be?
  3. What’s your go-to karaoke song?
  4. What’s the weirdest food you’ve ever tried and liked?
  5. If you could only eat one food for the rest of your life, what would it be?
  6. Do you believe in aliens, and what do you think they’d think of us?
  7. If you were a pirate, what would your pirate name be?
  8. What’s the funniest joke you know?
  9. If you had to be trapped in a TV show for a month, which one would you choose?
  10. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
  11. What’s your spirit animal, and why?
  12. If you had to live in a fast-food restaurant, which one would it be?
  13. What’s the most useless talent you have?
  14. If you were a wrestler, what would your entrance song be?
  15. What’s your favorite cheesy pick-up line?
  16. If you were a kitchen appliance, which one would you be?
  17. What’s the worst hairstyle you’ve ever had?
  18. If you could have dinner with any three people (dead or alive), who would you pick?
  19. What’s the funniest nickname you’ve ever been given?
  20. What’s the weirdest dream you’ve ever had?
  21. Would you rather always have to speak in rhyme or sing instead of speak?
  22. If you were an ice cream flavor, which one would you be?
  23. What’s the most embarrassing thing you’ve ever done on a date?
  24. What’s the weirdest smell you actually kind of like?
  25. Would you rather have a pet dragon or be a dragon?
  26. If you could be a character in any movie, who would you be?
  27. If you had to be a Disney villain, who would you be?
  28. What’s your secret talent that no one knows about?
  29. What’s your silliest fear?
  30. What would you do if you won the lottery?
  31. Do you have a funny dance move you’d like to share?
  32. If you could swap lives with a cartoon character, who would it be?
  33. What’s a fashion trend you’re glad went away?
  34. If your life was a sitcom, what would the title be?
  35. What’s the most ridiculous thing you’ve ever believed?
  36. What’s the funniest WiFi name you’ve ever seen?
  37. If you had to survive a zombie apocalypse, what three items would you take?
  38. Would you rather always have to wear clown shoes or a clown wig?
  39. What’s a word you can never spell correctly on the first try?
  40. What’s your “guilty pleasure” song?
  41. If you were a superhero, what would your weakness be?
  42. What’s the weirdest thing you’ve ever eaten on a dare?
  43. Would you rather fight a chicken every time you get into a car or fight an orangutan once a year?
  44. What’s a movie that you can quote way too much of?
  45. Do you have any weird eating habits?
  46. What’s the strangest place you’ve ever been to?
  47. If you had to eat a crayon, what color would you choose?
  48. Would you rather have a rewind button or a pause button on your life?
  49. What’s your funniest gym fail story?
  50. If you could talk to animals for a day, what would you ask them?

About Yourself

  1. What was your first impression of me?
  2. Do you think I’m funny?
  3. What’s your favorite thing about me?
  4. Do you think we have stuff in common?
  5. How would you describe me in three words?
  6. What’s something you think I’m really good at?
  7. Do you think I’m a good listener?
  8. What’s the nicest thing I’ve ever done for you?
  9. Do you think I’m shy or outgoing?
  10. Do you think I’m more of a morning person or a night owl?
  11. What’s a song that reminds you of me?
  12. How do you feel when we’re apart?
  13. What’s your favorite memory with me?
  14. If you could change one thing about me, what would it be?
  15. Do you think I’m good at making decisions?
  16. What’s a talent you think I have?
  17. Do you think I’m easy to talk to?
  18. If I were an animal, what do you think I’d be?
  19. What’s a food that makes you think of me?
  20. How do you feel when I’m the one who texts first?
  21. Do you think I’m more of a leader or a follower?
  22. How would you feel if I made the first move?
  23. Do you think I’m brave?
  24. What’s a movie that you think I’d love?
  25. Do you think I’m more into looks or personality?
  26. How would you feel if I cooked dinner for you?
  27. Do you think I’m romantic?
  28. How do you feel when I compliment you?
  29. Do you think I have a good sense of style?
  30. What’s your favorite outfit that I wear?
  31. How do you think I handle stress?
  32. Do you think I’m more of an introvert or extrovert?
  33. What’s something you wish I knew about you?
  34. Do you think I’m stubborn?
  35. If we were stranded on an island, do you think we’d survive?
  36. What’s a book you think I should read?
  37. How do you feel when we disagree on something?
  38. What’s something you think I should try?
  39. Do you think I’m patient?
  40. How do you feel when I hug you?
  41. What’s a trip you’d like to take with me?
  42. What’s a hobby you think I’d be good at?
  43. Do you think I’m a positive person?
  44. How would you feel if I surprised you?
  45. Do you think I’m good with money?
  46. How do you feel when I say I miss you?
  47. Do you think I’m good at keeping secrets?
  48. Do you think I’m close with my family?
  49. What’s a talent you wish I had?
  50. If you could give me any gift, what would it be?
  51. Do you think I’m good at giving advice?
  52. How do you feel when we laugh together?
  53. What emoji reminds you of me?
  54. Do you like my sense of humor?
  55. What’s your favorite thing we’ve ever done together?
  56. How would you feel about meeting my friends?
  57. Do you think I’m reliable?
  58. What’s something I’ve said that stuck with you?
  59. If we were in a band, what instrument would I play?
  60. How do you feel when we run into each other unexpectedly?
  61. Do you think I’m a dreamer or a realist?
  62. Do you like the way I smell?
  63. What’s your favorite quality of mine?
  64. How do you feel when I touch your hand or arm?
  65. Would you want to dance with me?
  66. Do you think I’m the competitive type?
  67. How do you feel about my driving?
  68. What’s your favorite photo of us?
  69. If you could pick a place for us to go on a date, where would it be?
  70. Do you like the way I kiss?
  71. Do you think I’m organized or messy?
  72. Do you think I’d be a good parent someday?
  73. How would you feel if I wrote you a love letter?
  74. What sport do you think I’d be good at?
  75. Do you like my taste in music?
  76. Do you think I’m a fast learner?
  77. How do you feel when we’re in a crowd together?
  78. Do you think I’d be good at a game show?
  79. Do you like it when I show affection in public?
  80. Do you think I’d be good at camping?
  81. How would you feel about a road trip with me?
  82. Do you think I’m the kind of person who likes challenges?
  83. What color do you think looks best on me?
  84. What nickname would you give me?
  85. How would you feel about cooking together?
  86. Do you think I’m into high fashion or comfort?
  87. How do you feel when I’m sick?
  88. Do you think I handle arguments well?
  89. Would you say I’m more of a city or a country person?
  90. What would be our perfect weekend together?
  91. Do you think I take risks?
  92. How do you feel when I say something sweet?
  93. Do you think I’m a good dancer?
  94. Do you like my family?
  95. Would you say I’m more chill or high-energy?
  96. What’s a goal you think I should aim for?
  97. Do you think I’m good with animals?
  98. How would you feel about a surprise vacation?
  99. Do you think I’m good at planning surprises?
  100. What’s a moment with me that you’ll never forget?

About Love and Relationships

  1. What’s your idea of a perfect relationship?
  2. Do you believe in soulmates?
  3. What’s the most important thing in a relationship for you?
  4. What’s your love language?
  5. How do you handle disagreements in a relationship?
  6. What’s the most romantic thing you’ve ever done?
  7. Do you like grand gestures of love or small acts of kindness?
  8. What’s your deal-breaker in a relationship?
  9. How do you know when you’re in love?
  10. What’s your opinion on long-distance relationships?
  11. How would you feel about dating someone with different religious beliefs?
  12. Do you think couples should have shared hobbies?
  13. How do you feel about public displays of affection?
  14. What’s the longest relationship you’ve ever been in?
  15. What’s the best relationship advice you’ve ever received?
  16. What’s a mistake you think people often make in relationships?
  17. Do you think “opposites attract” is true?
  18. What’s your go-to romantic date?
  19. How important is physical attraction to you?
  20. How do you feel about sharing passwords with a partner?
  21. Do you think age matters in a relationship?
  22. What’s a lesson you’ve learned from a past relationship?
  23. What’s your opinion on couples who work together?
  24. How do you feel about pet names in a relationship?
  25. Do you believe in love at first sight?
  26. How important is communication to you in a relationship?
  27. Would you move for love?
  28. Do you think couples should live together before getting married?
  29. How do you feel about social media and relationships?
  30. What’s your idea of the perfect proposal?
  31. Do you think it’s okay to keep secrets in a relationship?
  32. What’s the most meaningful gift you’ve ever received?
  33. How do you feel about sharing finances with a partner?
  34. How important is family approval in a relationship for you?
  35. What’s your opinion on having kids?
  36. How do you feel about dating a friend’s ex?
  37. Do you think chemistry is more important than compatibility or vice versa?
  38. How would you like to celebrate anniversaries?
  39. What’s the best way to say “I love you” without using words?
  40. How do you feel about couples’ therapy?
  41. What’s your take on open relationships?
  42. Do you have a “type“?
  43. How do you handle jealousy in a relationship?
  44. What’s more important to you: passion or stability?
  45. What do you think about couples who have a “hall pass“?
  46. How do you feel about dating someone with a different cultural background?
  47. What’s the most romantic place you’d like to visit?
  48. How long do you think people should date before getting engaged?
  49. Do you believe in “the one“?
  50. What’s your opinion on marriage; is it an outdated institution or still relevant?

About Random Fun Stuff

  1. If you could hang out with any fictional character, who would it be?
  2. What’s your favorite ice cream topping?
  3. If you could time travel, what era would you visit?
  4. What’s your all-time favorite video game?
  5. If you could have dinner with three celebrities, who would they be?
  6. What’s your favorite theme park ride?
  7. What’s the most unusual hobby you’ve ever tried?
  8. If you were on a deserted island, what three books would you want with you?
  9. What’s your go-to snack at the movies?
  10. Would you ever go skydiving?
  11. What’s the coolest magic trick you’ve seen?
  12. If you had a magic lamp, what would your three wishes be?
  13. What’s your favorite board game?
  14. Are you a morning person or a night owl?
  15. What’s your go-to karaoke song?
  16. Do you have any hidden talents?
  17. If you were a superhero, what would your superpower be?
  18. What’s the weirdest food combination you actually enjoy?
  19. What’s your favorite animal, and why?
  20. If you had to eat only one cuisine for a month, what would it be?
  21. Do you prefer the beach or the mountains?
  22. What’s your favorite type of dance?
  23. If you could switch lives with a historical figure for a day, who would it be?
  24. What’s the craziest adventure you want to go on?
  25. What’s your favorite way to waste time?
  26. Do you have a favorite planet?
  27. What’s the most interesting documentary you’ve ever seen?
  28. If you had to be on a reality TV show, which one would you choose?
  29. What’s your favorite type of puzzle?
  30. What’s the most interesting fact you know?
  31. If you could own any type of animal as a pet, what would it be?
  32. What’s your favorite joke?
  33. Do you enjoy roller coasters?
  34. What’s your favorite kind of weather?
  35. If you could be any fictional villain for a day, who would you be?
  36. What’s the best concert you’ve ever been to?
  37. Do you like stargazing?
  38. What’s your dream car?
  39. If you had to listen to one song for the rest of your life, what would it be?
  40. What’s your favorite sport to watch?
  41. Do you have any weird superstitions?
  42. What’s the best costume you’ve ever worn?
  43. If you could have any job for one week, what would it be?
  44. What’s your favorite type of tea or coffee?
  45. What’s the most interesting place you’ve ever visited?
  46. Do you believe in ghosts?
  47. What’s your favorite holiday and why?
  48. Would you rather be a famous actor or a famous musician?
  49. What’s the most daring thing on your bucket list?
  50. What’s your favorite cheesy joke?

About Their Interests

  1. What’s your favorite book and why?
  2. Who’s your favorite musician or band?
  3. Do you like to cook? What’s your best dish?
  4. What’s your favorite sport to play?
  5. What TV show are you currently binge-watching?
  6. Do you have a favorite artist or painting?
  7. What’s the last movie that you really loved?
  8. Do you like to garden or take care of plants?
  9. Are you into video games? Which ones?
  10. What’s your favorite way to exercise?
  11. Do you have a favorite podcast?
  12. What’s your go-to comfort food?
  13. Do you enjoy hiking or outdoor activities?
  14. Are you a coffee person or a tea person?
  15. What hobbies do you wish you had more time for?
  16. Are you into any extreme sports like skateboarding or skydiving?
  17. Do you like photography?
  18. What’s the last concert or live performance you went to?
  19. Do you have a favorite genre of music?
  20. Do you enjoy crafting or DIY projects?
  21. What kind of movies make you cry?
  22. Are you a fan of any sports teams?
  23. What’s your favorite type of dance?
  24. Do you like to draw or paint?
  25. What’s your dream vacation destination?
  26. Are you into history? Any favorite periods?
  27. Do you like to write, maybe poems or stories?
  28. What’s your favorite type of exercise?
  29. Do you enjoy watching documentaries?
  30. Are you a fan of any YouTube channels?
  31. Do you like going to museums or galleries?
  32. What’s your favorite play or musical?
  33. Do you like board games or card games?
  34. What’s your favorite animal to see at the zoo?
  35. Are you interested in fashion?
  36. Do you like fishing or camping?
  37. What’s your favorite season and why?
  38. Are you into astrology?
  39. Do you enjoy cooking shows?
  40. What’s your favorite type of candy?
  41. Do you like puzzles or brain teasers?
  42. Do you enjoy visiting theme parks?
  43. What’s your favorite type of video content to watch?
  44. Do you have a favorite superhero?
  45. Are you into fitness and wellness?
  46. Do you enjoy biking or cycling?
  47. What’s your favorite holiday tradition?
  48. Do you like to collect anything?
  49. Are you a fan of animated shows or movies?
  50. What’s your favorite way to unwind after a long day?

About Movies and Music

  1. What’s the last movie you watched?
  2. Do you prefer action movies or comedies?
  3. Who’s your all-time favorite movie character?
  4. What movie do you think is overrated?
  5. Have you ever walked out of a movie because it was bad?
  6. Which movie has the best soundtrack, in your opinion?
  7. Do you like watching foreign films?
  8. Who’s your favorite movie director?
  9. What’s your favorite movie quote?
  10. Do you like horror movies?
  11. What’s a movie that made you laugh really hard?
  12. Have you ever watched a movie more than three times in the theater?
  13. Do you prefer watching movies at home or in a theater?
  14. What’s the saddest movie you’ve ever watched?
  15. What’s your favorite movie trilogy or series?
  16. What was the last concert you went to?
  17. What song is currently stuck in your head?
  18. Do you play any musical instruments?
  19. What’s your favorite music video?
  20. Do you have a go-to workout song?
  21. What was the first album you ever bought?
  22. Who’s your favorite singer?
  23. Do you like live music?
  24. What’s a song you know all the lyrics to?
  25. Do you like to dance? What’s your favorite song to dance to?
  26. What’s a song that always makes you happy?
  27. Do you have a favorite music genre?
  28. What’s your favorite song to sing in the shower?
  29. Do you have a song that reminds you of your childhood?
  30. What’s a song that you think everyone should listen to?
  31. What movie do you think has the worst soundtrack?
  32. Do you like musicals? If so, which is your favorite?
  33. What song would make a great theme for a movie about your life?
  34. If you could be a character in a musical, who would you be?
  35. Have you ever listened to a film score just for fun?
  36. What’s your favorite Disney song?
  37. Do you like watching music documentaries?
  38. What’s a good song that was ruined by a movie?
  39. If you could make a soundtrack for a movie, what kind of movie would it be?
  40. What musician would you like to see act in a movie?
  41. Do you ever watch movies just for the soundtrack?
  42. What’s your favorite movie adaptation of a musical?
  43. Who’s a musician you think would make a great movie director?
  44. What’s a movie you love but hate its soundtrack?
  45. Do you have a favorite film composer?
  46. What’s a song you wish was in a movie?
  47. If your life was a movie, what song would play in the credits?
  48. Have you ever discovered a musician or band through a movie?
  49. What’s a classic movie you think needs a modern song in its soundtrack?
  50. What’s a movie you wish you could see turned into a musical?

About Food and Favorites

  1. What’s your all-time favorite meal?
  2. Do you like spicy food?
  3. What’s your go-to fast-food order?
  4. What’s a dish you can cook really well?
  5. Do you have a favorite type of bread?
  6. Ice cream or gelato?
  7. What’s your favorite fruit?
  8. Do you like sushi?
  9. What’s your favorite type of cheese?
  10. Do you prefer salty snacks or sweet treats?
  11. What’s a food you could eat every day and not get tired of?
  12. What’s the strangest thing you’ve ever eaten?
  13. Are you a fan of seafood?
  14. What’s your favorite breakfast food?
  15. Do you prefer coffee, tea, or hot chocolate?
  16. What’s your favorite type of pie?
  17. Do you like to grill food?
  18. Do you have a favorite restaurant?
  19. What’s your favorite international cuisine?
  20. Do you like trying new foods, or do you stick to what you know?
  21. What’s your favorite color?
  22. Do you have a favorite number?
  23. What’s your favorite season of the year?
  24. Do you have a favorite flower?
  25. What’s your favorite sport to watch?
  26. What’s your favorite book genre?
  27. Do you have a favorite quote?
  28. What’s your favorite holiday?
  29. What’s your favorite type of weather?
  30. Do you have a favorite brand of clothing?
  31. What’s your favorite type of exercise?
  32. What’s your favorite way to relax?
  33. Do you have a favorite scent or perfume?
  34. What’s your favorite day of the week?
  35. What’s your favorite type of shoe?
  36. Do you have a favorite cartoon from childhood?
  37. What’s your favorite board game?
  38. Do you have a favorite app on your phone?
  39. What’s your favorite way to travel?
  40. What’s your favorite city that you’ve visited?
  41. What’s your favorite dessert to make at home?
  42. Do you have a favorite recipe book?
  43. What’s your favorite type of cake?
  44. What’s your favorite fruit juice?
  45. What’s your favorite milkshake flavor?
  46. What’s your favorite wine or cocktail?
  47. What’s your favorite cooking show?
  48. Do you have a favorite kitchen gadget?
  49. What’s your favorite meal of the day: breakfast, lunch, or dinner?
  50. What’s your favorite holiday dish?

About Travel and Adventure

  1. Have you ever traveled outside of your country?
  2. What’s the most beautiful place you’ve ever been to?
  3. Do you prefer the beach or the mountains?
  4. What’s your dream travel destination?
  5. Have you ever gone on a solo trip?
  6. What’s the longest flight you’ve ever been on?
  7. Do you prefer road trips or flying?
  8. What’s your favorite type of vacation: relaxing or active?
  9. Have you ever been on a cruise?
  10. What’s a travel destination that you think is overrated?
  11. Do you like camping?
  12. What’s your go-to travel snack?
  13. How many states or countries have you visited?
  14. Have you ever been backpacking?
  15. Do you collect souvenirs when you travel?
  16. Have you ever gone skydiving or bungee jumping?
  17. What’s the most adventurous thing you’ve ever done?
  18. Do you like hiking?
  19. Have you ever gone scuba diving or snorkeling?
  20. What’s an outdoor activity you want to try but haven’t yet?
  21. Have you ever gone on a hot air balloon ride?
  22. Do you enjoy winter sports like skiing or snowboarding?
  23. Have you ever gone whitewater rafting?
  24. Do you like horseback riding?
  25. What’s the most daring food you’ve tried?
  26. Have you ever been ziplining?
  27. Do you enjoy cycling?
  28. Have you ever participated in an adventure race?
  29. What’s the most challenging physical activity you’ve done?
  30. Would you go on a treasure hunt?
  31. What’s the most off-the-beaten-path place you’ve visited?
  32. Do you like to plan out your trips or be spontaneous?
  33. Would you ever want to live in another country?
  34. What’s your ideal travel companion: friends, family, or significant other?
  35. What’s a festival or event you’d like to travel to?
  36. Have you ever taken a cooking class in another country?
  37. What’s your favorite travel memory?
  38. What’s the first thing you do when you arrive at a new travel destination?
  39. Have you ever taken a scenic train journey?
  40. What’s your must-have travel item?
  41. Do you prefer luxury hotels or cozy inns?
  42. Have you ever volunteered while traveling?
  43. What’s the most romantic place you’ve visited?
  44. Do you prefer city travel or countryside visits?
  45. Have you ever been on a safari?
  46. What’s your favorite way to document your travels?
  47. Do you enjoy local street food when traveling?
  48. Have you ever been lost while traveling? What happened?
  49. Would you travel to space if you could?
  50. What’s the next place on your travel bucket list?

About Future Plans

  1. What’s your dream job?
  2. Where do you see yourself in 5 years?
  3. Do you want to have kids someday?
  4. What’s a skill you’d love to learn in the future?
  5. Do you plan to stay in your current city long-term?
  6. Would you ever want to start your own business?
  7. What’s a goal you want to achieve in the next year?
  8. Do you have a dream car you’d like to own one day?
  9. Is there a charity you’d like to be more involved with in the future?
  10. Do you have a dream wedding in mind?
  11. Would you like to go back to school or get another degree?
  12. What’s the next big purchase you’re saving up for?
  13. Do you see yourself living in a house or an apartment in the future?
  14. What’s a hobby you’d like to take up when you have more time?
  15. Are you planning to travel to a specific place soon?
  16. Would you like to work abroad one day?
  17. Is there a mentor or role model who inspires your career goals?
  18. Do you see yourself sticking with your current job long-term?
  19. Do you have a “retirement dream” like sailing around the world or writing a book?
  20. What’s a job you’d never want to have, no matter how well it pays?
  21. Do you want a big family or a small one?
  22. What’s an ideal age for you to settle down?
  23. Do you think you’ll be a strict parent or a cool parent?
  24. How do you feel about long-term commitments or marriage?
  25. What’s something you’re looking forward to in your personal life?
  26. Is there a physical feat like running a marathon that you want to achieve?
  27. What’s one thing you want to do to improve yourself?
  28. Is there a cause or issue you’re passionate about that you’d like to dedicate time to?
  29. Do you have a bucket list? What’s at the top?
  30. What’s a bad habit you want to break in the future?
  31. If you could design your dream home, what’s one feature it would have?
  32. What’s a pet you’d like to have one day?
  33. Would you ever go on a reality TV show?
  34. Do you plan to get any tattoos or piercings in the future?
  35. What’s a concert or event you’re looking forward to attending?
  36. What’s a book you plan to read soon?
  37. Is there a specific place you want to move to in the future?
  38. Do you have plans to change your lifestyle, like becoming vegan or more active?
  39. What’s an investment you’re thinking of making?
  40. Are you planning to take up any new sports or activities?
  41. Is there a language you want to learn?
  42. Do you have any plans for further studies or courses?
  43. What’s your next big adventure?
  44. Are you planning to join any clubs or social organizations?
  45. What’s something you want to do as soon as you retire?
  46. Do you see yourself ever going on a long-term journey or expedition?
  47. Is there a side hustle you’re considering starting?
  48. What’s an event or milestone you’re most looking forward to in the next decade?
  49. Would you like to write a book or start a blog?
  50. Are there friends or family you’re planning to reconnect with in the future?

About Friends and Family

  1. Who is your oldest friend?
  2. How do you usually meet new friends?
  3. What do you and your friends like to do on weekends?
  4. Have you ever been on a road trip with friends?
  5. Do you have a friend who has really influenced your life?
  6. What’s the craziest adventure you’ve had with a friend?
  7. Do you have a go-to person for advice?
  8. How do you handle conflicts with friends?
  9. What qualities do you value most in a friend?
  10. Do you have a friend who you think is really funny?
  11. Have you ever lost a friend? How did it happen?
  12. How often do you catch up with old friends?
  13. Do you have any work friends?
  14. What’s your favorite memory with a friend?
  15. Are most of your friends from school, work, or someplace else?
  16. How many siblings do you have?
  17. What’s your favorite family tradition?
  18. Do you have a big family or a small one?
  19. How often do you visit your hometown?
  20. Do you look more like your mom or your dad?
  21. What’s your favorite family holiday?
  22. How close are you with your extended family?
  23. Do you have a family member who you really look up to?
  24. What’s a recipe that has been passed down in your family?
  25. Have you ever gone on a big family vacation?
  26. Who is the funniest person in your family?
  27. Do you have any family pets?
  28. What’s the best piece of advice a family member has given you?
  29. Do you have family movie nights?
  30. Who’s the cook in your family?
  31. Do your friends know your family well?
  32. What’s a trait you think you’ve inherited from your family?
  33. Do you think friends can be like family?
  34. Have you ever taken a friend to a family gathering?
  35. Who are you closer to, your friends or your family?
  36. What’s something your friends would be surprised to know about your family?
  37. Do you have a childhood friend you’re still close to?
  38. How does your family feel about your friends?
  39. Have you ever had to choose between a friend and a family member?
  40. What’s a value or belief you share with your family and friends?
  41. Do you and your family have inside jokes?
  42. Have any of your friends ever dated one of your siblings?
  43. Do you and your family have a favorite game to play together?
  44. How do you introduce new friends to your family?
  45. How do you deal with friends your family doesn’t like?
  46. What’s a song that reminds you of your friends or family?
  47. Do you and your family have a favorite restaurant?
  48. Is there a book or movie that you enjoy and have recommended to friends and family?
  49. How have your friends influenced your relationship with your family?
  50. Do you think you’re more like your friends or your family?

About School or Work

  1. What was your favorite subject in school?
  2. Did you play any sports in school?
  3. Were you part of any clubs or groups in school?
  4. Did you like high school or college better?
  5. What’s your favorite school memory?
  6. Did you ever pull an all-nighter studying?
  7. What was the hardest class you ever took?
  8. Did you have a teacher who really inspired you?
  9. Did you go to your school prom?
  10. Have you ever cheated on a test?
  11. What’s the most fun project you’ve ever worked on in school?
  12. Did you ever skip class?
  13. How did you usually get to school?
  14. Did you ever win any school awards?
  15. Were you a good student, or did you struggle?
  16. What was your first job?
  17. What do you like most about your current job?
  18. Have you ever had a really tough boss?
  19. Do you have work friends?
  20. How do you handle stress at work?
  21. Do you prefer working alone or in a team?
  22. Have you ever had to fire someone?
  23. What’s the most challenging part of your job?
  24. Do you have a side hustle?
  25. What’s the most interesting project you’ve worked on?
  26. Do you like to dress up for work or keep it casual?
  27. How do you usually commute to work?
  28. Have you ever pulled an all-nighter for work?
  29. What’s the funniest thing that’s happened at your workplace?
  30. Do you see yourself staying in your current job for a long time?
  31. Would you ever go back to school to change careers?
  32. How did your school experience prepare you for work?
  33. Do you still keep in touch with friends from school or old coworkers?
  34. What’s a skill you learned in school that you use at your job?
  35. Have you ever had to move for school or work?
  36. What’s a common misconception people have about your job?
  37. Did you have an internship that helped you in your career?
  38. Have you ever been the new kid at school or the new person at work?
  39. Do you prefer practical experience or academic knowledge?
  40. What’s the best career advice you’ve ever received?
  41. Did you ever do something in school or work that you regret?
  42. Have you ever been really proud of a grade or work accomplishment?
  43. Is there a subject you wish you’d paid more attention to in school?
  44. How do you continue to learn and grow in your career?
  45. Do you mentor anyone or have a mentor yourself?
  46. Do you have a routine for getting ready for school or work?
  47. What’s your go-to lunch for a busy day?
  48. Have you ever had to give a presentation or speech? How did it go?
  49. What’s the biggest lesson you’ve learned from school or work?
  50. If you could go back in time, would you choose the same career or study the same subject?

About Their Childhood

  1. Where did you grow up?
  2. What’s your earliest memory?
  3. Did you have a favorite toy as a kid?
  4. Were you a troublemaker or a good kid?
  5. What was your favorite game to play outside?
  6. Did you go to summer camp?
  7. Did you have a childhood pet?
  8. What cartoons did you watch?
  9. Did you learn to ride a bike? Who taught you?
  10. What was your favorite subject in elementary school?
  11. Did you ever have an imaginary friend?
  12. What’s your favorite childhood snack that you still eat?
  13. Did you have a treehouse or a secret hideout?
  14. What was your go-to childhood outfit?
  15. What did you want to be when you grew up?
  16. How did you get along with your siblings?
  17. Did you live close to your grandparents?
  18. Who was your best friend in elementary school?
  19. Did you ever run away from home, even if just to the end of the street?
  20. What was your family’s first computer?
  21. Did you play any musical instruments?
  22. Were you in any kids’ clubs, like Scouts or a sports team?
  23. What was the first movie you saw in theaters?
  24. Did you ever collect anything, like stamps or coins?
  25. What was the best birthday party you had?
  26. What was the best gift you ever got as a kid?
  27. Did you believe in Santa Claus or the Tooth Fairy?
  28. How do you usually celebrate your birthday?
  29. What’s a family holiday tradition you loved?
  30. Did you have a special place your family went to for vacations?
  31. Did you ever get caught doing something you shouldn’t?
  32. What’s a funny story your family always tells about you?
  33. Did you ever get a really bad haircut?
  34. What’s something silly you believed as a kid?
  35. Did you have a childhood nickname?
  36. What was your favorite book as a kid?
  37. Do you have a favorite lullaby or song?
  38. What scared you the most when you were little?
  39. Did you ever have to go to the hospital for something silly, like swallowing a Lego?
  40. What was the first sport you played?
  41. Did you ever win any trophies or medals as a kid?
  42. What’s a TV show you were not allowed to watch?
  43. Did you have chores? Which one did you hate the most?
  44. Were you a picky eater?
  45. What was the first thing you saved up money to buy?
  46. Did you have a favorite blanket or stuffed animal?
  47. What was the name of your first crush?
  48. Did you ever write a letter to someone famous?
  49. What was the first concert or event you went to?
  50. What would your younger self think of you now?

About Social Media Habits

  1. What’s your go-to social media app?
  2. Do you follow any celebrities? Who’s your favorite?
  3. What’s the funniest meme you’ve seen lately?
  4. Do you watch YouTube? What kind of channels do you like?
  5. How often do you check social media every day?
  6. Do you prefer watching stories or scrolling through posts?
  7. Have you ever been in a group chat that got way too chaotic?
  8. Do you like sharing selfies or more scenery pictures?
  9. What’s the last song you shared on social media?
  10. Do you use social media to stay updated on the news?
  11. Have you ever taken a break from social media?
  12. What’s the most interesting account you follow?
  13. Do you use any apps to help you unplug or relax?
  14. Have you ever done a social media challenge? Which one?
  15. What’s your favorite hashtag to follow?
  16. Do you have any online friends you’ve never met in person?
  17. What’s the weirdest DM you’ve ever received?
  18. Do you follow any food blogs or recipe pages?
  19. Have you ever had to block someone? Why?
  20. How do you feel about getting tagged in photos?
  21. Do you watch or post TikToks?
  22. What’s your favorite filter or photo effect?
  23. Do you keep your profile public or private?
  24. Have you ever regretted a post and deleted it?
  25. What’s your most-liked picture?
  26. Do you use social media for work or just for fun?
  27. Have you ever used a dating app?
  28. Do you read the comments on public posts?
  29. Have you ever participated in an online discussion or debate?
  30. How do you pick what to post on your feed?
  31. Do you enjoy inspirational quotes or posts?
  32. Do you follow any sports teams or athletes online?
  33. Have you ever bought something because you saw it on social media?
  34. Do you follow any travel blogs or pages?
  35. What’s your opinion on people who overshare on social media?
  36. Have you ever won a giveaway or contest online?
  37. Do you post more when you’re happy or when you’re down?
  38. Have you ever helped out in an online campaign or charity?
  39. Do you watch live streams? What kind?
  40. How do you feel about people who post every detail of their day?
  41. Do you think you act the same online and in real life?
  42. Have you ever had a post go viral?
  43. Do you follow any pets or animals on social media?
  44. Do you use any fitness or health apps?
  45. Have you ever gotten into a new hobby because of social media?
  46. Do you have any favorite online games or challenges?
  47. What’s the most heartwarming thing you’ve seen online?
  48. Do you enjoy watching unboxing or review videos?
  49. Have you ever met someone in real life that you first met online?
  50. What would you do if social media suddenly disappeared one day?

About Sports and Fitness

  1. Do you have a favorite sports team?
  2. Ever played on a sports team?
  3. Do you watch the Olympics?
  4. What’s the craziest sports game you’ve ever been to?
  5. How do you feel about fantasy sports?
  6. Do you like any solo sports like swimming or tennis?
  7. Have you ever run a marathon or a 5K?
  8. Do you like extreme sports?
  9. Ever tried something like golf or fishing?
  10. How about martial arts or boxing?
  11. Do you have a regular workout routine?
  12. Gym or home workouts?
  13. Do you like group exercise classes?
  14. Ever done yoga or pilates?
  15. What’s your go-to cardio exercise?
  16. Do you like to watch sports live or on TV?
  17. Have you ever tried a new sport just because it looked fun?
  18. Do you have a favorite athlete?
  19. Do you like indoor or outdoor activities more?
  20. Do you follow any sports blogs or podcasts?
  21. What’s your proudest sports moment?
  22. Ever had a sports injury?
  23. Do you like to play sports video games?
  24. Have you ever coached a team or taught a sport?
  25. Did you play sports as a kid?
  26. Do you like hiking or nature walks?
  27. Ever been skiing or snowboarding?
  28. Do you like water sports like kayaking or paddleboarding?
  29. What’s your ideal way to stay active on vacation?
  30. Do you count your steps or use a fitness tracker?
  31. Do you like playing casual games like frisbee or cornhole?
  32. Ever tried an unusual sport like archery or curling?
  33. Do you like to dance as a form of exercise?
  34. What’s a sport you’re really bad at but enjoy anyway?
  35. Do you like watching extreme sports?
  36. Do you follow a specific diet for fitness?
  37. What’s your go-to post-workout snack?
  38. Do you take any fitness supplements?
  39. How do you stay hydrated during a workout?
  40. Do you meal prep for the week?
  41. Do you have any fitness goals right now?
  42. Planning to try any new sports soon?
  43. Do you ever do fitness challenges?
  44. Would you ever consider a career in sports or fitness?
  45. What’s a sport you’ve never tried but want to?
  46. Do you watch sports documentaries?
  47. Do you prefer team sports or individual sports?
  48. How do you feel about esports?
  49. Do you have any sports memorabilia?
  50. Do you like sports movies?

About Pets and Animals

  1. Do you have any pets?
  2. What was the name of your first pet?
  3. Have you ever had an unusual pet, like a snake or a tarantula?
  4. Do your pets do any funny tricks?
  5. If you could have any pet in the world, what would it be?
  6. Dogs or cats?
  7. Do you prefer big dogs or small dogs?
  8. Would you ever own a bird?
  9. Are you more into mammals, birds, or reptiles?
  10. Do you think fish are boring pets?
  11. Did you grow up with pets?
  12. Have you ever raised a pet from when it was a baby?
  13. Did you ever have a pet run away?
  14. Did you ever bring home a stray animal when you were a kid?
  15. Did you ever have a pet that had babies?
  16. Do you spoil your pets?
  17. Do you cook for your pets?
  18. How do you feel about dressing up pets in clothes?
  19. Do you talk to your pets like they’re people?
  20. Do you give your pets human names or goofy names?
  21. What’s your favorite wild animal?
  22. Have you ever been on a safari?
  23. What animal would you be most excited to see in the wild?
  24. Do you like going to the zoo or animal sanctuaries?
  25. Have you ever touched a really dangerous animal?
  26. What animal do you think you’re most like?
  27. What’s the cutest animal in the world, in your opinion?
  28. Do you follow any cute animal accounts on social media?
  29. Have you ever seen an animal do something really smart?
  30. What’s the funniest animal video you’ve ever seen?
  31. Do you think animals have personalities?
  32. Would you ever want to keep chickens for fresh eggs?
  33. How do you feel about animal actors in movies?
  34. Do you like going horseback riding?
  35. Do you think aliens have pets?
  36. How do you feel about using animals for testing?
  37. Do you think animals should have rights?
  38. What’s your opinion on hunting?
  39. Do you believe in the ethical treatment of livestock?
  40. Would you ever become a vegetarian or vegan for ethical reasons?
  41. Do you plan on adopting any pets in the future?
  42. Would you ever get a pet as a couple’s activity?
  43. If you were to get a new pet, what would you name it?
  44. How many pets are too many?
  45. Could you date someone who doesn’t like pets?
  46. What animal do you wish you could talk to?
  47. If pets could answer one question, what would you ask?
  48. What’s an animal that you don’t get why people like?
  49. Do you believe in mythical animals like unicorns or Bigfoot?
  50. What’s your Patronus? (Or what do you think it would be?)

About Fears and Challenges

  1. Are you afraid of heights?
  2. Do you have any phobias?
  3. How do you deal with fear?
  4. Are you afraid of the dark?
  5. Do spiders freak you out?
  6. What’s your biggest fear in relationships?
  7. Are you scared of getting too attached?
  8. What’s your biggest fear in life?
  9. Do you worry about the future?
  10. Are you afraid of being alone?
  11. What’s the hardest thing you’ve ever done?
  12. Have you ever conquered a big fear?
  13. What’s a challenge you’re proud of overcoming?
  14. Have you ever stood up for something you believe in, despite the risk?
  15. What was your most physically demanding challenge?
  16. Does public speaking make you nervous?
  17. Are you afraid of flying?
  18. Do you find social situations challenging?
  19. Is there something that scares you but you wish it didn’t?
  20. Do you fear failure?
  21. What’s a fear you’ve never told anyone?
  22. Do you believe that what doesn’t kill you makes you stronger?
  23. What keeps you up at night?
  24. Do you have any regrets?
  25. Do you think fear is necessary?
  26. How do you prepare for a challenge?
  27. Do you like to face your fears head-on?
  28. When was the last time you stepped out of your comfort zone?
  29. Do you think facing your fears is exhilarating or terrifying?
  30. How do you build courage?
  31. What’s a future challenge you’re not looking forward to?
  32. Are you scared of getting old?
  33. Do you worry about climate change?
  34. What’s a skill you find challenging but want to learn?
  35. Do you fear missing out on opportunities?
  36. Are you afraid of commitment?
  37. Is it hard for you to trust people?
  38. Do you fear being judged by others?
  39. Are you afraid of losing someone you love?
  40. Do you find it challenging to make new friends?
  41. What personal challenge are you currently facing?
  42. Do you fear you won’t achieve your dreams?
  43. How do you handle rejection?
  44. Are you afraid of change?
  45. Do you find it challenging to express your emotions?
  46. What’s a silly fear you have?
  47. Are you scared of any movie monsters?
  48. What’s the scariest book you’ve ever read?
  49. Do you like watching horror movies?
  50. What’s a challenge you would never take on, no matter what?

About Their Bucket List

  1. What’s the number one place you want to visit?
  2. Do you want to see all seven wonders of the world?
  3. Is there a specific festival around the world you want to attend?
  4. Would you ever want to go on a hot air balloon ride?
  5. Do you dream of going on a safari?
  6. Have you ever thought about skydiving?
  7. Do you want to try bungee jumping?
  8. How about scuba diving? Ever wanted to explore the ocean?
  9. Would you like to go on a long hike or trek?
  10. Have you ever wanted to go on a road trip with no set plan?
  11. Is there a musical instrument you’ve always wanted to learn?
  12. Do you want to become fluent in another language?
  13. Have you ever wanted to write a book?
  14. Is there a type of dance you’d love to master?
  15. Do you have a cooking or baking challenge on your list?
  16. Is there a dream job you’re aiming for?
  17. Do you want to start your own business?
  18. Is there a big charity event you want to organize?
  19. Have you ever thought about going back to school or taking special courses?
  20. Do you want to achieve something big in your current job?
  21. Is volunteering in another country on your list?
  22. Do you have a cause you want to raise awareness or money for?
  23. Have you ever wanted to mentor someone?
  24. Do you dream of making a difference in someone’s life?
  25. Is there a charity you’d like to start?
  26. Is there something you’re afraid of that you want to face?
  27. Do you want to complete a physical fitness challenge?
  28. Have you thought about going on a meditation or wellness retreat?
  29. Do you aim to read a certain number of books?
  30. Is there a famous landmark you want to climb or hike?
  31. Is there a concert or event you dream of attending?
  32. Do you want to be part of a big celebration, like Mardi Gras or Carnival?
  33. Would you like to see the Northern Lights?
  34. Do you have a favorite artist you want to see in a live show?
  35. Have you ever wanted to be in a TV show or movie, even as an extra?
  36. Do you want to break a world record?
  37. Is there a food challenge you want to try?
  38. Would you like to be a game show contestant?
  39. Do you want to meet a celebrity?
  40. Have you ever wanted to try an extreme sport?
  41. Do you want to own a dream car or house?
  42. Is there a specific place you want to get married or propose?
  43. Do you want to have kids, and how many?
  44. Is there a particular way you’d like to celebrate a big birthday?
  45. Do you want to renew your vows when you’ve been married for a certain number of years?
  46. Is there an odd or funny skill you want to learn?
  47. Do you want to visit a place just because of its weird name?
  48. Is there a silly world record you want to break?
  49. Have you ever wanted to be a flash mob participant?
  50. Do you want to send a message in a bottle?

Frequently Asked Questions

How can I use these questions to take things to the next level?

Questions can be a stepping stone to a deeper connection. If your crush seems interested and engaged, and their answers align well with your own thoughts and feelings, it might be a good sign to move forward. However, make sure to respect their comfort zone and let things progress naturally.

What if I’m too shy to ask questions?

If you’re shy, you might find it tough to break the ice with your crush. But remember, questions are your friends! You can start with simple, low-risk questions that can be tucked into casual conversation. Something like, “Have you seen any good movies lately?” is easy to ask and can lead to more interesting topics.

Tip: Texting is also a less intimidating way to ask questions if you’re not quite ready for face-to-face chats.

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Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.