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220 Questions to Ask Your Crush to Learn Who They Really Are

Asking the right questions will clue you in to just how compatible the two of you really are.

We all fantasize about people we're crushing on, but building up an image of someone without really getting to know them can cause serious problems down the line. That's why we've put together an extensive list of questions to ask your crush. We've also segmented them into categories so that you can be more discriminating about what kinds of questions you ask and when. At best, these prompts will help uncover even more amazing truths about a potential partner. At worst, they'll help you determine just how compatible the two of you really are—before those fantasies develop into real feelings.

RELATED: 21 Questions For a New Relationship.

Questions to Ask Your Crush Over Text

woman laying in bed texting her crush
  1. Who was your first celebrity crush?
  2. What's your favorite movie?
  3. What do you spend way too much money on?
  4. What's your most impressive skill?
  5. When are we hanging out next?
  6. What's one song that you know word-for-word?
  7. What's your biggest guilty pleasure?
  8. What's the most memorable trip you've ever taken?
  9. Can you describe your dream job?
  10. Do you play any instruments?
  11. What's your favorite animal?
  12. Fiction or non-fiction?
  13. How many pairs of shoes do you own?
  14. Are you a cat person or a dog person?
  15. What's your favorite restaurant?
  16. Do you live by yourself?
  17. Who was the first musical artist you ever got obsessed with?
  18. What's the best meal you've ever eaten?
  19. What's one movie you can watch over and over again and not get sick of?
  20. What's your favorite form of exercise?
  21. Where did you go to school?
  22. Do you get stage fright?
  23. What's your favorite food?
  24. What's your biggest pet peeve?
  25. Which famous person is your dream dinner guest?
  26. Would you rather be rich or famous?
  27. What are some of your favorite vices?
  28. Do you prefer small towns or cities?
  29. What's your favorite color?
  30. Are you a morning or night person?
  31. What do you think your next big purchase will be?
  32. Do you like huge parties or do you prefer to spend time in smaller groups?
  33. What's your favorite TV show?
  34. Do you have any recurring dreams?
  35. What's your favorite cocktail?
  36. What's your favorite childhood memory?
  37. If you could only bring three things to a deserted island, what would you pack?
  38. What's the next thing on your bucket list?
  39. What did you study in college?
  40. What's your favorite possession?
  41. Would you rather stay in a beach house or a cottage in the woods?
  42. Do you watch reality television?
  43. Do you have any allergies?
  44. What shows are you currently watching?
  45. What are you looking for in your next relationship?
  46. What's your favorite season?

RELATED: 290 Important Questions to Ask Your Girlfriend Before Getting Serious.

Deep Questions to Ask Your Crush

two men having a deep conversation while sitting on a hill overlooking the city
Dumblin Films/Shutterstock
  1. Have you ever broken someone's heart?
  2. What's something your younger self would not believe about your life today?
  3. Why did your last relationship end?
  4. What do you think your life's purpose is?
  5. What's your biggest fear?
  6. What part of your past would you like to relive?
  7. What part of your past would you like to rewrite?
  8. How do you usually handle conflict?
  9. Who in this world knows you the best?
  10. What's your biggest regret?
  11. How do you define love?
  12. How long do you think people should date before committing to a relationship?
  13. What's your sexual orientation?
  14. Have you noticed any type of pattern in past relationships that you'd like to avoid during your next?
  15. Do you think maintaining strong friendships is just as important as finding a romantic connection?
  16. Do other people consider you shy or outspoken?
  17. What's your elevator pitch in a job interview?
  18. What's your biggest deal breaker in a new relationship?
  19. If you could live anywhere in the world, where would you choose to live?
  20. How important are appearances to you?
  21. What are you scared of not accomplishing?
  22. What sort of things do you most enjoy doing alone?
  23. What's more important, physical attraction or meaningful conversations?
  24. Do you have any personal milestones?
  25. What do you think the biggest lesson you've ever learned was?
  26. If you could pass just one quality into your children, what would it be?
  27. What's a secret you've never told anyone?
  28. Do you think you're living life to the fullest?
  29. What's one memory you wish you could erase forever?
  30. Would you rather be incredibly intelligent or incredibly happy?
  31. What expectations do you have for a partner?
  32. What's the most frustrating part about modern dating?
  33. How do you define cheating?
  34. How many days a week would you like to spend with a new partner?
  35. What are your thoughts on sex before monogamy?
  36. Would you expect your partner to take an active interest in something you're passionate about?

RELATED: 241 Clever Questions to Ask a Guy On the First Date.

Yes or No Questions to Ask Your Crush

woman holding two post-it notes reading, "yes" and "no"
  1. Do you think I'm cute?
  2. Have you ever dated a friend's ex?
  3. Do you get jealous easily?
  4. Do you consider yourself relatively tech-savvy?
  5. Did you vote in the last election?
  6. If you won a billion dollars would you still choose to work?
  7. Are you still close with your childhood friends?
  8. Have you ever broken any bones?
  9. Do you freak out about bugs?
  10. Are you close with your extended family?
  11. Do you usually sleep soundly through the night?
  12. Did your parents meet your ex?
  13. Have you thought about me yet today?
  14. Do you like cuddling?
  15. Do you think only guys should make the first move?
  16. Do you think you're ready for your next relationship?
  17. Would you ever go to a nude beach?
  18. Do you ever get tongue-tied?
  19. Are you a good kisser?
  20. Do you want to be more than just friends?
  21. Have you ever been skinny dipping?
  22. Have you ever had your heart broken?
  23. Do you have a short fuse?
  24. Do you still have any of the stuffed animals you played with as a kid?
  25. Do you believe in love at first sight?
  26. Did you have a happy childhood?
  27. Do you want to have kids someday?
  28. Are you interested in pursuing a serious relationship?
  29. Have you ever cheated on a partner?
  30. Do you spend a lot of money on clothes?
  31. Are you close to your parents?
  32. Do you have any savings?
  33. Do you think individuals of the opposite sex can really be just friends?
  34. Do people find it easy to trust you?
  35. Have you ever visited a psychic?
  36. Is cereal a type of soup?
  37. Do you snore?

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

Funny Questions to Ask Your Crush

man and woman laughing together in a cafe
  1. What's your go-to karaoke song?
  2. What's the most embarrassing moment you can remember?
  3. What's the worst lie you've ever told?
  4. Can you describe the worst date you've ever been on?
  5. Who is the last person you would want to run into on the street?
  6. Who would be your celebrity pass if you were in a relationship right now?
  7. If you had to be a Disney character, who would you choose?
  8. What's your favorite type of cheese?
  9. Can you do any good impressions?
  10. What's the most useless invention of all time?
  11. What's the most annoying animal out there?
  12. What do you think people will be nostalgic for in 40 years?
  13. When was the last time you had "an accident" in public?
  14. How do you play it off after you trip over something?
  15. How do you feel about body hair?
  16. If you had to change your name, what name would you choose?
  17. What's the creepiest thing you could say to a stranger when passing them on the street?
  18. Who's your favorite comedian?
  19. What's your worst habit?
  20. If someone based a movie on your life, what genre would it be and who would play you?
  21. How long do you think you'd last in a zombie apocalypse?
  22. What's your least favorite smell?
  23. If you had to compete on a cooking show, what dish would you make during the audition?
  24. What sport would be a lot more entertaining to watch if the players were drunk?
  25. Would you rather have no nose or no arms?
  26. How do you feel about pineapple on pizza?
  27. What actually came first—the chicken or the egg?
  28. What could work as an alternative name for peanut butter?
  29. What famous people do you follow on social media?
  30. Would you rather have X-ray vision or the power of invisibility?
  31. What's the most embarrassing thing you've ever worn?
  32. How many chickens do you think it would take to kill an elephant?
  33. Do you know any good jokes by heart?
  34. What's the best excuse you've ever come up with for getting out of work?
  35. What's the weirdest thing you've ever seen in someone else's home?
  36. What's the most imaginative insult you can think of?
  37. If you had to become an influencer, what would be your niche?
  38. Do you think you have a celebrity lookalike?
  39. What do you think would make a better pet, a hamster or a rabbit?
  40. What's something you're terrible at?
  41. What used to be trashy but is now classy?
  42. What was something you splurged on that you now regret?

RELATED: 271 Essential Questions to Ask Your Boyfriend Before Getting Serious.

Flirty Questions to Ask Your Crush

hipster man and woman on a first date at a cafe
William Perugini/Shutterstock
  1. Can you describe your dream date night?
  2. What was your first impression of me?
  3. What's your love language?
  4. What's your zodiac sign?
  5. What do you do on a typical Saturday?
  6. What do you find attractive about me?
  7. What's your favorite sex position?
  8. Do you prefer the lights on or off?
  9. How do you feel about dirty talk?
  10. Do you have a favorite word?
  11. Do you prefer cuddling or kissing?
  12. How would you react if I kissed you the next time I saw you?
  13. What's the craziest thing you've ever done on a first date?
  14. Can you tell me the best joke you know?
  15. Do you have any sexual kinks?
  16. Have you always been this funny?
  17. What are some of your biggest turn-ons?
  18. What's your favorite thing about me?
  19. What's the most embarrassing thing that's ever happened to you on a first date?
  20. What's the best hobby a partner could have?
  21. What do you think of my outfit?
  22. If I wanted to cook a meal for you, what should I prepare?
  23. Have you ever had a dream about me?
  24. What part of the body are you most attracted to?
  25. How often do you work out?
  26. Where's the strangest place you've ever had sex?
  27. Do you have any tattoos? If so, can I see?
  28. What did you think when we first met?

RELATED: 228 Questions You Definitely Want to Ask a Girl on a First Date.

Sweet Questions to Ask Your Crush

man and woman flirting on a first date
  1. How was your day?
  2. How old were you when you had your first kiss?
  3. What's the most romantic thing you've ever done for someone else?
  4. What's the best compliment anyone has ever given you?
  5. What's the best gift you've ever been given?
  6. In your opinion, what would be the perfect date?
  7. Who is your favorite person in the world?
  8. How long have you known your best friend?
  9. What's the biggest surprise you've ever received?
  10. What helps calm you down when you're feeling stressed?
  11. What's something you're looking forward to?
  12. Have you ever been in love?
  13. Is there anyone that looks up to you as a role model?
  14. What impact do you hope to make on those around you?
  15. What's your favorite cocktail?
  16. If you had to sum up your life's philosophy in one sentence, what would it be?
  17. What accomplishment are you most proud of?
  18. What are you looking for in a potential partner?
  19. What's your favorite thing about being in a relationship?
  20. What excites you most about the future?
  21. When is your birthday?
  22. If a genie granted you three wishes, what would you ask for?
  23. Would you rather plan a special date or have someone plan one for you?
  24. What makes you nervous?
  25. How direct would you want someone who had feelings for you to be?
  26. How would your mother describe you to others?
  27. What's one major milestone you hope to experience in the future?
  28. What inspires you to be a better person?
  29. Are you an only child or do you have siblings?
  30. What was your nickname growing up?
  31. What's your favorite quote from a TV show or movie?

Tips for Approaching Your Crush With Questions

Woman using laptop and taking notes in notebook
El Nariz/Shutterstock

Make sure you remain an active listener.

If you're going to ask the hard-hitting questions, the least you can do is pay attention when someone starts serving up answers. Doing so demonstrates a genuine interest in what your crush has to say. It also helps you gather more material for follow-up questions, and studies have shown that people like people who continue with questions more than those who don't. So, let them talk and listen carefully.

Only ask questions you want to know the answers to.

As the old adage goes, "Don't ask questions if you don't want to know the answer." If the two of you actually end up together, you'll surely end up learning a lot about them. But for now, there's no harm in keeping it light. Spare yourself some drama, and only ask about subjects you're comfortable hearing about—at least for now.

Allow them to ask you questions back.

Don't turn the exchange into an interrogation. Allowing your crush to ask you questions in return will probably make them feel more comfortable. And that will likely result in them feeling close enough to you to reveal more than they otherwise would.

Wrapping Up

That's it for our list of questions to ask your crush but be sure to check back with us soon for even more tips on life, love, and relationships.

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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