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Questions to ask your crush

If we had to choose each other's outfits for a night out, how much trust would you have in me?Jump to this question ↓

Sometimes it's hard to come up with questions to ask your crush and still sound casual. That's why I came up with this list of questions. Hopefully it will help you strike up a conversation and get to know your crush a little bit better.

Questions: 168

Questions to start talking

  1. What’s your favorite thing to do on the internet?
  2. What do you spend most of your time doing?
  3. What’s your favorite thing to shop for? Why?
  4. What was the most beautiful view you have ever experienced?
  5. What fad have you held on to, even though it isn’t popular anymore?
  6. What country do you not know the location of even though you should?
  7. What's something you would happily spend an afternoon watching somebody make?
  8. What's something you like better when it's a little worn out?
  9. Which local business would you be sad to see close even though you never go in?
  10. What's something you like hearing someone talk about even though you have no interest in doing it yourself?
  11. What do you still do the hard way on purpose?
  12. What kind of place makes you start whispering even when you don't have to?
  13. What's a place you like much more at night?
  14. When you find a song you like, do you want someone else to hear it immediately, or do you keep it to yourself for a while?
  15. If you loved a painting, would you rather hear what the artist meant by it or keep your own version?
  16. What do you pay attention to when you're eating alone that you don't notice when you're with someone?
  17. What do your friends still expect you to like even though you grew out of it years ago?
  18. What's something you would rather learn from a stranger than from a friend?
  19. What do you wish people would invite you to more often?
  20. What would I have to learn about to follow a conversation between you and your closest friends?
  21. Whose footsteps could you recognize without seeing them?
  22. Which of your friends would be hardest to explain to someone who hadn't met them?
  23. Is there someone whose stories you enjoy enough to let them get away with exaggerating?
  24. Who would you put in charge of telling you when you're taking yourself too seriously?
  25. When you walk into a room, do you look for a good seat or a good person to sit next to?
  26. What would you warn me about before I met your oldest friend?

Funny questions to ask your crush

  1. What do you find hilarious but most people don’t find funny?
  2. When was the last time you tried to do something to look cool and it ended in utter embarrassment?
  3. What is the most cringe worthy thing you have seen someone post on social media?
  4. What is the most ridiculous rule you have to follow?
  5. Who do you have a hard time taking seriously?
  6. What’s something that people go on and on about, and you just can’t take sitting through?
  7. What do you have a hard time with but most people find quite easy?
  8. What’s a huge story in the news that you care absolutely nothing about?
  9. What would you sneak onto a very serious person's playlist?
  10. Which romantic movie scene would be much less romantic if it happened to you?
  11. What is the most effort you've put into making something look accidental?
  12. When have you had to stop telling a story because the person you were talking about walked in?
  13. Have you ever gone along with someone else's ridiculous plan because you wanted to see how far they'd take it?
  14. When did you realize that something you thought was fancy was actually cheap?
  15. What's the difference between your 'I'm listening' face and your 'I have absolutely no idea what you're talking about' face?
  16. What would you buy immediately if somebody made a tiny working version of it?
  17. If somebody challenged us to be silent for ten minutes, what would you do to make me laugh?
  18. What would be a funny thing for two people to discover they were both trying to hide on a first date?
  19. What would you put on a postcard to make your hometown look like a terrible place to visit?
  20. How often do you end up being the sensible one against your own will?
  21. What would you be doing right now if you weren't being responsible?
  22. When have you been deep into a conversation before realizing you were talking about two different people?
  23. Who in your life would be most suspicious if you suddenly started dressing better?
  24. How long would you watch me struggle with something silly before offering to help?
  25. What do you think I'd do well at for all the wrong reasons?
  26. If we put up a 'Free advice' sign, what would you hope nobody asked us about?
  27. What would be a ridiculous reason for two people to break up that you would secretly understand?
  28. If we found a locked box on the beach, what would you hope would be inside?
  29. What should come with a practice round before it counts?
  30. What would you like to be asked to name that nobody should trust you to name?
  31. Which 'life hack' sounds like more work than just doing the thing?
  32. Which shop would be the funniest place to get banned for life from?
  33. If you had a conspiracy theorist cork board with photos, red string, and push pins, what would it be about?
  34. Are you better at making someone laugh on purpose or by accident?
  35. What would convince you to join in with strangers who were dancing?
  36. Would you pay more or less for a hotel room if the receptionist said it had been the scene of an unsolved mystery?
  37. Could you date a songwriter knowing every argument might end up on an album?
  38. What did you volunteer for once and somehow end up being in charge of forever?

Questions about their stories and interests

  1. What was the best year of your life so far?
  2. What do you spend way too much money on?
  3. What’s something you can do that most people can’t?
  4. What is your worst getting trolled story?
  5. What bullet have you recently dodged?
  6. What’s the most impressive skill you have?
  7. When was the last time you went somewhere intending to stay only ten minutes and stayed for hours?
  8. Have you ever spoiled the ending of something for yourself because you couldn't stand not knowing?
  9. Have you ever become friends with someone because you both hated the same thing?
  10. What's something you want to finish before you tell people you've started it?
  11. What would you refuse to buy if the seller seemed too eager to get rid of it?
  12. What's something you would happily spend a whole evening helping someone with?
  13. Would you be pleased or annoyed if someone returned a book you lent them with their favorite lines underlined?
  14. What's the smallest thing you've ever treated as a special occasion?
  15. What have you stopped making fun of since you tried it yourself?
  16. What's the nicest place you've ever had a terrible time?
  17. Have you ever decided you respected someone more after watching them lose?
  18. What's an argument you've enjoyed losing?
  19. What have you made for someone that you still wonder whether they kept?
  20. What would you ask the person who lived in your home before you?
  21. What have you agreed to go to or do and then had to look up what it was?
  22. What's a promise to yourself that you keep breaking for a perfectly good reason?
  23. Have you ever started something just to prove a person wrong or on a dare and ended up liking it?
  24. Which stranger do you still wonder about because you only got half their story or the encounter was too short?
  25. How do you react when someone loves the thing you recommended for a completely different reason?
  26. What's something you've done very carefully that nobody noticed?

Flirty questions to ask your crush

  1. What’s the best compliment that someone can receive?
  2. Have you ever realized someone was flirting with you about six months too late?
  3. Would you want a friend to tell you if someone liked you, or would you rather find out for yourself?
  4. Have you ever been disappointed to find out someone was single because it meant you might actually have to do something about liking them?
  5. Do you like holding hands with the person you are dating when you walk around together?
  6. If I fell asleep on your shoulder, how long would you let me stay there?
  7. If you knew I was about to ask you out, would you make it easier for me or enjoy watching me try?
  8. Have you ever liked someone's voice before you knew what they looked like?
  9. If a stranger thought we were together, how quickly would you correct them?
  10. Do you enjoy the part where neither person has admitted they like the other yet?
  11. If someone gets flustered while trying to compliment you, does that make it better or worse?
  12. Could you flirt successfully using only questions about the weather?
  13. Would you be more nervous about meeting someone's friends or letting them meet yours?
  14. What would you notice first if I was trying to look less nervous than I felt?
  15. How do you act around someone who has caught you staring at them?
  16. Which is worse, asking someone out and getting a no, or finding out years later that you both liked each other?
  17. What would convince you to leave a party early with me?
  18. Would you tell someone you liked them if the only time you could get them alone was in an elevator?
  19. Do you want to know when someone has made an effort to look good for you, or would you rather they played it cool?
  20. When you're excited about someone, who in your life gets tired of hearing about them first?
  21. Has anyone ever made you lose your train of thought just by looking at you?
  22. Can you enjoy flirting with someone you know you'd be terrible at dating?
  23. What would you ask me if I promised not to dodge the question?
  24. Could you be won over by someone who was terrible at flirting but very good at making you breakfast?
  25. Would you tell someone before a first kiss that you were nervous?

Questions to ask your crush over text

  1. Would you rather I waited until I had something clever to say, or just send a text when I thought of you?
  2. Do you ever save a message because you like the way the person said something?
  3. When was the last time you caught yourself smiling at your phone and hoped nobody would ask what it was?
  4. Would you open a message from me marked 'don't open this at work' straight away or wait until you got home?
  5. At what point in getting to know someone do you stop tidying the background before a video call?
  6. Which bit of our last conversation should we have kept going with?
  7. What happened today that would have been funnier if I'd been there?

Questions about spending time together

  1. Would a twenty-minute coffee with me improve your day or just make you late?
  2. What would you add to a picnic to make it feel like an occasion?
  3. How much would you trust your friends to pick where to go on a date for you?
  4. Would you be annoyed if a date went exactly as planned and there was nothing funny to tell your friends afterward?
  5. Would you rather I asked you out with a plan already made or gave you a choice of things we could do?
  6. What would you want to do differently if we met a second time?
  7. What would make a bad first date worth a second try?
  8. What would you stop to show me if we were walking through your neighborhood?
  9. If we took a terrible photo together that made us both laugh, would you keep it or insist on a better one?
  10. If we ordered something to share, would you keep track of whether we'd had equal amounts?
  11. Would you rather tell me a story that makes you look good or one you know will make me laugh?
  12. If we started making up a story about the people at the next table, who would turn out to be the villain?
  13. If we picked each other something to read, would you try to impress me or give me something you actually like?
  14. If we had to make a meal using only things from one aisle of the supermarket, which aisle would you pick?
  15. What would you do with a free afternoon in a town where everything had closed?
  16. If we went to a wedding together, would you head for the dance floor or find somewhere to talk?
  17. Are you better company when you've planned something or when you've got nowhere to be?
  18. What would you be quietly relieved to find out I was bad at?
  19. If I asked you to come with me somewhere without telling you where, what would you need to know before you said yes?
  20. If we went somewhere you knew everyone and I knew nobody, who would you introduce me to first?
  21. What game could you teach me without needing to look up any rules?
  22. If I joined you for your favorite hobby, what would I get told off for first?
  23. If I asked you for a recommendation, would you give me your favorite or the one you thought I'd like?
  24. If I started winning a game you'd taught me, would you be pleased with yourself or annoyed with me?
  25. If we had to choose each other's outfits for a night out, how much trust would you have in me?
  26. If we had to sit through a terrible movie together, would you want me to behave or help you make fun of it?
  27. If I cooked for you and it was awful, how long would you let me think I'd done a good job?

More personal questions

  1. How do you calm yourself down when you are angry?
  2. What event small or large has changed the course of your life the most?
  3. What is something you have read or heard that has stuck with you for a long time?
  4. What do you judge people for most often?
  5. If we met after a long day, would you want to tell me everything or do something that helped you forget it?
  6. What's the longest you've waited around because you didn't want to say goodbye?
  7. What would you want me to remember after we'd spent a day together?
  8. Would you like your future self more if they had kept your current opinions or changed most of them?
  9. Which part of the day would improve most if you had some company?
  10. When you need some time to yourself, do you say so or find an errand to run?
  11. Have you ever been relieved when something you were supposed to want didn't happen?
  12. When does remembering little things about you feel sweet, and when does it feel like someone has been doing research?
  13. Have you ever enjoyed waiting for something more than the thing itself?
  14. What do you enjoy more when nobody is trying to make it special?
  15. What would you ask someone who had the life you previously thought you wanted?
  16. What do you think you would miss about your life now if one of your big plans worked out?
  17. If you could read one review written about you, would you choose one from a stranger, a friend, or someone you dated?
  18. What do you hope someone notices about you after they've known you for a while?
  19. Have you ever wished people would stop praising you for something because it wasn't what you wanted to be known for?

Questions to ask your crush PDF and image

Here's a PDF of the original 25 questions to ask your crushPDF · English · Questions · 317 KB.

Here's an image of the original 25 questions.

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