101 Questions To Ask Your Crush To Know Them Better

Ask these intriguing questions to discover the hidden, fascinating sides of your crush.

Reviewed by Dr Nancy B IrwinDr Nancy B Irwin, PsyD
By Harini NatarajanHarini Natarajan, Certified Emotional Intelligence Practitioner  • 

You might have a ton of questions to ask your crush, but you get tongue-tied when you meet your crush. Your thoughts are muddled. While your heart races, your incredible personality goes unnoticed. Your only chance of having your fantasies come true is if you talk to them and show interest in their life. An interesting conversation is all you need to showcase your personality and help you stand out from the crowd.

In reality, it is not always easy to think of questions for your crush without showing your nervousness! So, let us help you! Take a look at these questions to start a conversation with your crush. It will also provide an opportunity to get closer to your crush and know them better. You need to muster your courage and ask all of these questions the next time you see them. Scroll down.

101 Things To Ask Your Crush

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  1. What do you find funny but most people don’t?
  2. What is your favorite thing to do on the internet?
  3. What do you love to do when you are free? What do you spend most of your time doing?
  4. What do you spend your money on? What are your guilty pleasures?
  5. What event has changed the course of your life the most? Was it happy or sad?
Quick Tip
Asking personal questions will help you know the person better. However, make sure the other person is not uncomfortable and you do not sound interrogatory.
  1. What do you secretly judge people for most often? Do you feel guilty about it?
  2. What is something you have read that has stuck with you to date?
  3. What is the best compliment you have ever received? Why is it so memorable for you?
  4. Is there something you can do that most people can’t? For example, playing an instrument, solving puzzles, etc.?
  5. How do you manage to calm yourself when you get angry?
  6. What is the most humiliating thing that has happened to you?
  7. What is the tackiest thing you have seen someone post on Facebook or Instagram? Did you react to it or ignore it?
  8. Are your parents/ guardians strict?
  9. What is a trending story in the news that you care very little about? Why doesn’t it interest you?
  10. If you get to choose a city, state, or country anywhere in the world to live in for at least the next ten years, where would it be and why?

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    1. What are you secretly afraid of?
    2. If you had the opportunity, what advice would you give your younger self?
    3. What is your definition of true love? Do you believe in love at first sight?
    4. If you had to choose between unlimited money and unconditional love, what would you pick?
    5. Who do you respect most in your life? Why?
    6. What is that one thing that can always make you smile, no matter what?
    7. What is your idea of a perfect date?
    8. What are you most passionate about?
Quick Tip
Asking about their passions will help you form a more realistic expectation of who your crush is in real life.
    1. What is the worst lie you have told? Did you ever get caught?
    2. Have you ever been in a serious relationship?
    3. When making the first move, who do you think should do it first? The girl or the boy?
    4. What attracts you most in members of the opposite sex (or the same sex if you are LGBTQ)?
    5. If I kiss you right now, what would you do? Will you be mad at me?
    6. What would your parents be super surprised to learn about you?
    7. What superpower would you like to have, if you could?

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        1. Who knows you the best in this entire universe?
        2. What would you do if you won a million-dollar lottery?
        3. Did you watch cartoons as a kid? What was your favorite show as a child? Would you still want to watch it?
        4. What is your favorite kind of music?
        5. What kind of movies do you like?
        6. Name your favorite movie. Why do you like it?
        7. What’s your favorite dish? Can you cook it by yourself?
        8. Do you like to cook?
        9. Are there any good books you would recommend for me?
        10. What is the name of your favorite show? Why do you like it?
        11. What are your hobbies? Do you still take time out to engage in them?
        12. Where did you grow up? What was your hometown like?
        13. What do you and your friends do when you guys hang out?
        14. What was your first job? What did you have to do?
        15. What is the next big thing that you are aiming for?

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        1. In your opinion, what sport would be the funniest to watch if the players had to consume a decent amount of alcohol before playing?
        2. Have you ever watched a musical? What was your experience like?
        3. What is something that people have to do but look absolutely stupid doing?
        4. If animals could talk, which one do you think would have the most attitude?
        5. What is the scariest movie you have watched as a kid?
        6. What is the most ridiculous name you have heard of?
        7. What’s your favorite pizza topping?
        8. What can really annoy you in a person, whether you know them or not?
        9. Have you ever had any annoying guests at your place? What was the most ridiculous thing they did?
        10. What was the most immature thing your family ever did?
        11. What do you hope people would stop asking you?
        12. What areas of yourself do you want to work on? Have a devised a plan on how to do it?
        13. Do you think it is ok to lie sometimes? What if it is to protect someone’s feelings?
        14. Can one change their nature completely if conditioned by society?
        15. Would you sacrifice your life for someone? If yes, who?

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        1. What is the most important thing required in a happy and healthy relationship?
        2. What can make a person truly evil?
        3. What changes would you make to the state of our country, if you could?
        4. Do you make judgments about people quickly? How often are you correct?
        5. What is that one thing you wish you had never done?
        6. Would you prefer to be incredibly intelligent or incredibly happy?
        7. What is something you believe in that most people don’t?
        8. When have you been most anxious in life? What were you doing?
        9. Which celebrity do you have the hots for?
        10. What is your weirdest habit?
        11. What was the name of the last book you read? Why did you like it?
        12. What has been the best piece of advice that your parents gave you?
        13. Do you have any regrets? What’s the biggest one?
        14. Do you prefer the mountains or beaches for a holiday?
        15. Do you prefer big gala parties or small gatherings of close people?

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        1. Do you think everything is fated to happen, or are we in control of our own lives?
        2. Do you think Karma is real?
        3. Are you superstitious? Do you have any particular superstitions?
        4. Name a cheesy song that you love. Can you sing it for me?
        5. What is the kindest thing that someone has ever said to you?
        6. Do you prefer hanging out with no-nonsense, serious people or lighthearted people?
        7. Do you like to do things alone or be around people?
        8. Do you think you are living life to the fullest?
        9. Are you a spiritual person? Are you religious?
        10. Have you ever experienced heartbreak?
        11. Do you believe there is a purpose to life? Or is it all a meaningless, endless loop?
        12. Would you like to get married one day? Do you want kids? If yes, how many?
        13. What do you believe happens after death?
        14. If you could, would you eradicate pain from your life?
        15. Would you like to live forever? Why or why not?

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        1. Do you like routine or spontaneity?
        2. What is the biggest lesson about life you have learned?
        3. If you had to get a tattoo inked right now, what would you get, and where?
        4. Are you an introvert or an extrovert? Or an ambivert?
        5. What issues in today’s society make you most angry?
        6. Is there anyone in your life you wish you had met sooner?
        7. What kind of people do you least respect?
        8. Do you think we should choose our minds over our hearts?
        9. Are you a confident person?
        10. Do you have any siblings? Are you close to them?
        11. What is the worst date you’ve ever had?

Infographic Excerpt: 12 Deep Conversation Questions To Ask Your Crush

Do you get butterflies in your stomach every time your eyes meet? Well, you are not alone! The mere sight of your crush can make your heart beat faster and leave you full of happiness and excitement. But this can also make you feel nervous, and you might even run out of words. So, before you plan your next date with your sweetheart, run through the infographic below. This will help you to get ideas on how to have an engaging conversation.

12 deep conversation questions to ask your crush (infographic)

Illustration: StyleCraze Design Team

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Download Infographic in PDF version

Getting all nervous, sweaty, tongue-tied before your crush is nothing to be ashamed of. We have all been there. You prepare and practice before the mirror multiple times, but when you have a chance to talk to them, you struggle to find words. However, things can be quite different if you have a set of questions handy to keep the conversation alive and get to know your dream person better. The above list of questions to ask your crush will help you keep them engaged while giving them a chance to know you better. So, jot a few ideas down, take a deep breath, and let the conversations flow!

Frequently Asked Questions

How can you find out if your crush has a romantic interest in you through conversation?

Here are some signs that could show you that your crush is romantically interested in you:
• They focus more on you and maintain eye contact frequently.
• They attempt to carry on the conversation.
• They make physical contact.
• They positively respond to your questions.

How can I make sure I don’t make my crush feel uncomfortable when asking questions?

Be cautious of your crush’s comfort zone and boundaries while approaching them with questions. Begin with general questions and be mindful of the tone of your questions. Additionally, avoid asking them sensitive or private questions, and respect their choice to decline to answer if they don’t feel comfortable doing so.

Key Takeaways

  • It is natural to get tongue-tied when your crush is around you, but asking them funny and lighthearted questions can help you get talking.
  • You can ask them questions about their likes, dislikes, personal history, and outlook on life.
  • Remember, these questions are only conversation starters, and you need to carry on the conversation and take it to the next level.
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