What Are The Deep Questions to Ask Your Crush? Get over the Shyness and Act with These Questions

What Are The Deep Questions to Ask Your Crush? We Have the Solution You Have Been Waiting for. We all have had someone who can be considered our crush. Now, most people never manage to walk up to them and talk. They simply cannot express exactly what they are feeling. Now, if your crush is someone like a movie star or something, then, of course, you will never be able to get a chance to express your feelings. But if it is someone in your college, workplace, or neighborhood, then you still may have a chance. But how can you start the conversation?

Well, this is where this post comes to your aid. If you wish to make things easier for you, then we can help you with some questions you can ask your ex. These simple yet important questions will help you get the conversation started. We have some very interesting questions that can make the conversation interesting, and you never know; your crush might just say yes to your very first coffee date.

Let’s get started.

Why Is It So Difficult to Talk or Ask Deep Questions With Your Crush?

Having a crush is not necessarily having true feelings of love for someone. It is more of an infatuation. This is what makes everything so complicated between people. But this is where these questions can make things easier for you. 

deep question to ask your crush guide tips
Deep question to ask your crush guide tips

Now, you won’t feel so very awkward with your crush since we can make things smoother. 

  • These questions are more of conversation starters, something that has been your goal for a long time. 
  • At least, they can help you get an idea if, however, that person is interested in you at all or not. If he/she is not at all into you, then you can take the hint and leave the person alone, keeping your self-dignity intact. 
  • And if everything goes well and you manage to keep the conversation going, then, of course, you might just win a chance to go on a date with her.

Some Good Yet Deep Questions to Ask Your Crush

You don’t have to be too chatty, but you must surely initiate the conversation. One should not be too pushy yet find the right chord. For that, these questions can be perfect for you. They are usually general questions, but they are decent ones and help you understand the person as well. Let’s look at them one by one.

  1. What is that one thing you always look forward to in life?
  2. Tell me about the best compliment you have ever received
  3. Do you think we have any kind of similarity between us?
  4. Is there any suggestion in particular that you wish to give to people of your age?
  5. Tell me your most favorite food
  6. Do you know how to cook a meal?
  7. What would you be doing if you were not in your current profession?
  8. Tell me the best vacation you have ever had and where the place was.
  9. Tell me the three best places you wish to travel to next
  10. When you are low, what do you do to feel energized again?
  11. Do you vote every year? What is your political stand?
  12. Do you have any favorite authors?
  13. Do you have any tattoos? If not, would you like to have one someday?
  14. Suppose you take a sudden day off, how would you like to spend it?
  15. Do you have any favorite childhood memory?
  16. Is there anything about you that people usually fail to guess?
  17. Have you discovered any new artists that you can’t stop listening to lately?
  18. If you are stranded in a desert with just one album, which one would, that be?
  19. Who is your best friend? And how did you meet?
  20. When is your birthday?
  21. Tell me about the most beautiful or worst date you have been on.
  22. Have you ever volunteered for any charitable event?
  23. What has been your most favorite movie of all time?
  24. Do you have any random piece of trivia in your life?
  25. Do you have any favorite things that you wish to indulge in?
  26. Tell me about the first kiss you have ever had in your life and who the person was.
  27. Is there anything in your life for which you are really very proud?
  28. Are you a person who gets bored with things very easily?
  29. Do you have any siblings before or after you?
  30. How many cousins do you have?
  31. Do you always plan things ahead of your life, or do you like to be spontaneous?
  32. Is there anything on which you spend a lot of money?
  33. Tell me about the luckiest day of your life
  34. Have you been to any concert by any artist or band you love?
  35. Tell me the meaning of your name, and who gave you this name?
  36. Would you consider yourself a superstitious person?
  37. Do you think that you are very competitive?
  38. Tell me your preferred place to have a vacation and also the preferred itinerary
  39. Have you ever felt any sort of supernatural experience?
  40. What do you think can never go out of style?
  41. Tell me about something that’s popular and you think that deserves 100% of its hype.
  42. What is the best thing you like about being single? What are the things you don’t like about being single?
  43. Tell me the name of that famous personality around whom you will have a fanboy/fangirl moment
  44. What is the worst movie according to you?
  45. Were you very naughty when you were a kid?
  46. Do you have a go-to karaoke song on your song list?
  47. Do you have any kind of guilty pleasure in your life?

Some Deep Questions to Ask Your Crush and Start a Conversation

When you have a crush, the idea is to start talking to her and get to know her a bit better. After all, as we all know, communication is the key to everything. If you are not able to communicate, then things will never move forward in the right direction. So, here are a few questions that you should use to start a good conversation.

  1. Tell me about that one thing that you wish you never did
  2. Between being super intelligent and super-happy, which one would you choose?
  3. Is there anything that you believe must most other people don’t?
  4. Suppose you are granted a super-power for a day; what would you choose?
  5. Tell me the moment when you were the most nervous in your life
  6. Do you have a crush on any of the celebrities?
  7. What is the best city in the world according to you?
  8. What do you do when you are the happiest?
  9. Is there anything about your past that most people are absolutely unaware of?
  10. Do you have any dream destination where you wish to travel?
  11. Do you have any super bizarre habits?
  12. Tell me about your favorite movie ever
  13. Tell me about the last book you have read
  14. Tell me about the best piece of advice you have ever received from your parents
  15. Do you have any TV shows that you can binge on all day?
  16. What age has been the best phase of your life?
  17. Would you rather go back in time and advice yourself about something?
  18. Do you have any type of regrets in life?
  19. Between being in love and having a lot of money, which one would you choose?
  20. Between a beach or a mountain, which one would you choose?
  21. Suppose doctors told you that you are going to die in one month; how would you spend the rest of your days?
  22. Tell me your favorite musical genre and why it is your favorite.
  23. Suppose you are allowed to be incredibly skilled in something; what would you choose?
  24. Suppose you win a big lottery; what would you do with the money?
  25. Between being rich and famous and just being rich, which one would you choose?
  26. Suppose you can speak to the whole world one night; what would you like to say?
  27. If you become a talented rapper, what would you rap about?
  28. Is there anything that your friends tease you about? Like something you did in the past?
  29. Would you like to go to a big party or just small gatherings?
  30. What has been the worst time of your life?
  31. What, according to you, is the biggest deal-breaker?
  32. Suppose you become a fictional superhero; who do you want to be?
  33. Do you often blame your fate, or do you believe we can control our lives?
  34. Do you think that Karma exists?
  35. What is the one thing you find the most attractive in people?
  36. Do you read the newspaper? Do you have the habit of skipping any section?
  37. What is that one superstition you have in your life?
  38. Have you ever had any frightening experiences in your life?
  39. Do you have any favorite candidates for the presidential election?
  40. Tell me about the cheesiest song you love
  41. If you are allowed to have a dinner date with someone you love, whom would you choose?
  42. Do you have the habit of staying up to date with current affairs?
  43. Tell me about the best gift you have given to someone
  44. What is the best gift you have ever received?
  45. Do you use Apple phones or Android phones?
  46. If you become just the opposite gender for one day, how would you react to things?
  47. If you were given a huge or practically unlimited amount of money to buy your mother a gift, what would you gift?
  48. Tell me the kindest thing you have ever heard from someone
  49. Between a huge mansion and a cozy apartment, which one would you choose?
  50. Tell me the weirdest thing that happens in your family.

Some Deep Questions to Ask Your Crush and Know Her Better

When you have a crush, you would obviously wish to know her better, right? So how can you know more about her mindset and inner thinking? Asking the wrong questions can surely blow your chances for good. That’s why here are some questions you can easily try and have a wonderful conversation with her.

  1. Is there anything specific or abnormal that you do to calm yourself when angry?
  2. Do you often consciously try and look better in front of people?
  3. Do you have any definite rules in your life that you abide by?
  4. What is your favorite pastime activity?
  5. Is there anything that you spend money on but is actually a waste?
  6. Have you ever had any life-altering events in your life?
  7. Do you like serious people, or do you actually prefer light-hearted people?
  8. Is there any compliment that you receive regularly?
  9. Is there any particular thing that always drives you crazy about other people?
  10. Do you have any huge fear in your life?
  11. What is the feeling you get when your favorite music is being played?
  12. Tell me about the most emotional scene you have seen in a movie.
  13. Would you like to be alone or around people?
  14. When do you think the time is just flying around you, and you can’t seem to catch it?
  15. Do you believe that you are living your present life to its fullest?
  16. Tell me the kind of person you love being around the most
  17. What is your view on religion? Do you think it is good or bad?
  18. Would you call yourself a spiritual person?
  19. What does love mean to you in the broader sense?
  20. Have you ever felt heartbroken in your life?
  21. What is the one greatest thing you have ever accomplished in your life?
  22. When someone is saying “home,” then what do you feel?
  23. Is there anything that you always dream of?
  24. Do you believe that reality is beyond that what we can see with our eyes?
  25. What, according to you, is the purpose of your life? Or is it something completely meaningless?
  26. What is your view on marriage?
  27. What happens in our afterlife?
  28. What do you think can be done to eradicate the pain we feel in our life?
  29. Do you wish to live forever? Why would you want that?
  30. Between loving and being loved, which one would you choose?
  31. What is a true beauty, according to you?
  32. Is there any routine you like to have?
  33. What is the source of your biggest happiness?
  34. If I allow you to ask a question to me that I must answer truthfully, then what would that be?
  35. Tell me the best lesson you have had in your life
  36. Have you sorted out your priorities in life? Were they different in the past?
  37. Would you prefer to be rich and single or just poor but in love?
  38. Tell me about the hardest situation you’ve ever had in your life
  39. If you are asked to have a tattoo right now, then which one would you have?
  40. Do you think it is important to be kind to everyone, or just the near and dear ones are enough?
  41. Would you like to call yourself a very introvert or a very extrovert person?
  42. Whom do you hang out with more in life? Introvert or extrovert?
  43. Tell me the best trait you have in yourself
  44. Tell me about the worst trait you have in yourself
  45. What is that one thing you need to achieve before you die?
  46. When was that time you felt real awe in your life?
  47. What is that one single thing you completely hate seeing people do?
  48. Is there anything in society that makes you very much angry?
  49. What is your view on porn? Do you watch it?
  50. What is the one thing that motivates you the most in life?
  51. Is there anyone in your life that you wish you had met sooner?
  52. Is there any kind of people that you don’t respect at all?
  53. Between mind over matter or matter over mind, which one would you choose?
  54. What is that one moment when you feel super confident?

Some More Funny Yet Deep Questions to Ask Your Crush

When you have already become friends with your crush, now it is time to take things a bit forward. That’s why we have jotted down a few important questions which will help you make the bond even stronger. Here are such questions.

  1. What is your view on monogamy?
  2. How many times in your life so far have you fallen in love? 
  3. When was the first time you fell in love?
  4. When did your last relationship end? What was the reason behind it?
  5. Have you ever considered using the therapy?
  6. Tell me the kindest thing someone has done to you.
  7. Do you think something like a soulmate exists?
  8. Have you ever broken someone’s heart?
  9. Do you have any specific love language?
  10. What about phobias? Do you have any?
  11. What is your biggest fear in life?
  12. Do you feel that someone else’s approval is important to you?
  13. Tell me the last time you were really inspired by someone
  14. Whom do you respect, praise, and admire the most in your life?
  15. How do you wish to be comforted in life?
  16. Is there anything that you wish to learn more about?
  17. Are you good at keeping secrets?
  18. Did you ask your parents how did they meet each other?
  19. How do you resolve any kind of conflict in life?
  20. Do you think that the people that surround us play a role in our success?
  21. How do you deal with stress and anxiety?
  22. What is your proudest accomplishment in life?
  23. Do you believe in any theories as to what happens when we die?
  24. Do you have any idea how you will be in your old age?
  25. Is there anything you are unwilling to do?
  26. Have you ever cheated on someone? Or have you ever been cheated on?
  27. What is the most important thing you look for in your partner?
  28. What is the most important thing about yourself?
  29. Tell me about that one relationship you admire the most
  30. Is there anything about you that you wish to change?
  31. Who are you the closest to in your family?
  32. What is the one thing you hate about dating these days?
  33. Which year has been the most eventful in your life?
  34. Do you have any specific relationship deal-breaker?
  35. Do you always keep your guards on?
  36. Do you fall in love very easily?
  37. When it comes to relationships, what matters the most? Quality or quantity?
  38. Who is your oldest friend?
  39. Is there anything you wish to do in your next relationship?
  40. Do you have anything that you wish to re-do in life?
  41. Would you quit your job to follow your passion?
  42. How many kids do you wish to have?
  43. How religious would you call yourself?
  44. Do you take things slow or move quickly in a relationship?
  45. What is your view on mental health?
  46. Is there anything that you wish to be remembered for?

What Remains?

So, these are the deep questions you can ask when you have a crush on someone. I hope next time you meet your crush, you can use these questions. If you have any such personal experience, then do feel free to share that with us in the comments section. Your experience can help our readers a lot.


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