590 Deep Questions to Ask Your Crush to Keep Conversation Flowing

We’re quite confident we can improve your knowledge of the deep questions to ask your crush. Do you have a crush on someone you want to get to know a little — or a lot — better?

There’s an art to planting a love interest with deep questions to ask your crush that can help you measure compatibility while also striking the right blend of fun, playful, and inquisitive. In other words, you want to learn more about this individual.

You don’t want it to appear as though you’re interviewing or ambushing them. Of course, there isn’t a set formula for things you ask your crush to do here. Talking to someone you like may be nerve-racking enough without mentally crossing off a list of stuff to say and not to say in your brain!

But if you need a little assistance steering the discussion in a flirtatious and informative direction, we’ve done some of the legwork for you. Here are some deep questions for your crush to consider.

Super Deep Questions to Ask Your Crush

You’re vaulting right into the deep end with these super deep questions to ask your crush. These questions will help you understand about their dating habits, preferences, and dislikes. ‎ ‎

1. If you could be the opposite s#x for one day, what would you do?

2. What is the kindest thing someone has ever said about you?

3. Do you believe in astrology? Does your sign fit you?

4. What’s the most spontaneous thing you’ve ever done?

5. What is something that people misunderstand about you?

6. What is something that you would change about your life?

7. What do you think is your best quality?

8. If you go to a restaurant and have terrible service, is it ever OK not to tip?

9. Do you like serious people? Or do you prefer to hang around light-hearted people?

10. What do you do to calm yourself when you are angry?

11. What are you most scared of?

12. Did ever any food remind you of me? If so, then which food?

13. When was the last time when you thought about me in a good way?

14. What is your proudest accomplishment?

15. If you had a time machine, would you go back in time or visit the future?

16. Do you ever consciously try to look good in front of other people?

17. Which year of your life would you like to get a do-over, and why?

18. What is one thing you will never put up with?

19. If you have a free day, how do you usually spend it?

20. If you could only hear one song for the rest of your life, what would it be?

21. What does your ideal day necessarily involve?

22. Do you follow your mind or hear while making any important decisions in your life?

23. What is the one thing you spend money on when you know you shouldn’t?

24. What is the worst lie you’ve ever told your parents?

25. If you were a superhero, what kind of secret identity would you have?

26. What would your younger self not believe about your life today?

27. If any actor or actress could play you in a movie, who would it be?

28. What’s something that just makes time seem to fly by?

29. Do you feel like you’re living life to the fullest? If not, why?

30. What’s something that you are glad you will never need to do again in your life?

31. What would you do with a billion bucks if you were given it all at once?

32. What is one rule that defines your life?

33. What is one event that completely changed your perspective on life?

34. What should people in a healthy relationship get out of it?

35. Do you believe that everything happens for a reason, or do we just come up with explanations after the fact?

36. Would you prefer a huge mansion in a poor area or a small cozy apartment in a rich area?

37. If you had to get your mom one present and you could spend an unlimited amount, what would you get?

38. Is there anything that you absolutely refuse to forgive?

39. What would you do first if you wake tomorrow without fear?

40. When was the last time you cried?

41. What was one time you really stepped out of your comfort zone?

42. What is the biggest lesson you’ve learned?

43. Do you ever feel jealous when you see me talking or waking up to other attractive people?

44. What is the worst assumption someone has made about you?

45. What are some of your excellent qualities that you admire a lot?

46. What do you think about when you lie awake in bed?

47. What do you understand today about your life that you did not understand a year ago?

48. Are you holding onto something that you need to let go of?

49. What do you think is the greatest injustice in the world?

Very Deep Questions to Ask Your Crush

Tired of running out of questions to ask your crush? Or perhaps you’ve had a lengthy conversation with your crush and are at a loss for what to say next? Here are some very deep questions to ask your crush to keep things going.

1. When was your last relationship, and how did it end?

2. What is one thing you wish you never did?

3. Would you rather be incredibly intelligent or incredibly happy?

4. What’s something you believe that most people don’t?

5. Have you ever been to therapy?

6. If you could have one superpower for a day, what would it be?

7. When in life have you been most nervous?

8. Have you ever had your heart broken?

9. What celebrity do you have the biggest crush on?

10. What city has been the best city you’ve ever lived in or travelled to?

11. What’s your biggest fear?

12. What are you doing when you’re at your happiest?

13. What’s something about your past that most people don’t know about?

14. Is the approval of others important to you?

15. What’s the best piece of advice that you received from your parents?

16. What TV show could you just binge watch all day?

17. Have you ever broken someone else’s heart?

18. What age has been your best so far?

19. If you could go back in time and talk to yourself, what advice would you give?

20. When’s the last time you felt inspired to create something? What’d you create?

21. What’s the biggest regret you have?

22. Would you rather be in love or have a lot of money?

23. How do you like to be comforted when you’re sad or upset?

24. If you knew you would die in one month, what would you do?

25. If you could be incredibly skilled at one thing, what would you choose?

26 If you won the lottery, what would be the first thing you would do?

27. What’s your love language?

28. Would you rather be rich and famous or rich without the fame?

29. If you could contact the whole world and they would listen, what message would you give?

30. Who in life do you look up to most?

31. If you were an incredibly talented rapper, what would you want to rap about?

32. What’s something you did in your past that your friends still tease you about?

33. What’s something you’d like to learn more about?

33. What was the worst age you’ve been so far?

35. Do you believe in fate? Or are we in control of our lives?

36. Do you believe in Karma?

37. Do people trust you to keep secrets?

38. Do you stay up to date with current affairs?

39 What’s something you find attractive that most people don’t?

40. Do you have any superstitions?

41. What was the most frightening experience you’ve ever had?

42. Do you have any phobias?

43. What non-politician do you wish would run for office?

44. Have you ever lied about not doing something you were supposed to do?

45. What is the best gift you’ve ever given someone?

46. Aside from necessities, what one thing could you not go a day without?

47. Would you rather be feared by all or loved by all?

48. Would you rather lose all of your memories from birth to now or lose your ability to make new long-term memories?

Best Deep Questions to Ask Your Crush

You must exchange ideas, thoughts, and feelings with your crush in order to get to know them well. If you want to learn more about that, here are some of the best deep questions to ask your crush to help you get there.

1. Do you have a sneaking suspicion about how you’ll pass away?

2. If you had the chance to choose where you were born, where would it be?

3. Do I make an appearance in your dreams or fantasies?

4. What are you uncertain about?

5. What has taught you the biggest life lesson?

6. What’s the type of person you enjoy being around the most?

7. What are you most proud of having accomplished in the previous year?

8. What were your life’s big turning points?

9. Do you think religion has been a good thing or a bad thing for the world?

10. What is the one thing you have done you would want everyone to try?

11. When was the last time you pushed yourself past your limits? What was your reaction to it?

12. What is the happiest memory you have?

13. Do you think there is really life after death?

14. What do you do over and over again that you hate doing?

15. What’s the biggest thing you’ve done that you’ve been most proud of?

16. What has been one of the most essential life lessons you’ve learned?

17. What is the most audacious thing you’ve ever attempted?

18. When you hear the word “home”, what do you think of first?

19. How would you know someone is into you?

20. What’s the most consistent thing that you usually dream about?

21. Do you think that there’s more to reality than what we see with our eyes?

22. Do you think there is a purpose to life? Or is it all meaningless?

23. Name three things that you and your partner seem to share.

24. Apart from your known names, what another name would you like to be called?

25. What do you think happens after death?

26. If you could eradicate pain from your life, would you?

27. What would be the perfect way for someone to ask you out?

28. Would you rather love or be loved?

29. What does true beauty mean to you?

30. What has changed about you in the last five years?

31. When was the last time you sobbed, and why did you cry?

32. What do you think is the ultimate secret to happiness and living a fulfilling life?

33. Has failure shaped your life in any way?

34. Where do you think happiness comes from?

35. Through all of life’s twists and turns, who has been there for you?

36. What do you think our future holds for us? What direction do you think it’ll go?

37. What are your relationship objectives?

38. What would you alter about the way you were raised if you had the chance?

39. What are you most focused on at the moment?

40. If you have the power to change one thing about the world right now, what would you change?

41. What life lessons did you have to experience firsthand before you fully understood them?

42. Right now, at this moment, what do you want most?

Fun Deep Questions to Ask Your Crush

These fun deep questions to ask your crush keep things light and casual while yet ensuring an engaging conversation. These questions are more likely to elicit a response from your crush since they are not too personal but disclose just enough about them.

1. What qualities must the mother of your kids have?

2. When was the last time you laughed the hardest till now?

3. If you get a chance of listening to only one song for the rest of your life then what would you like to choose?

4. Would you rather leave your hometown and never be able to return, or stay in your hometown but never be able to go?

5. Have you ever felt guilty of pop culture pleasure? If so, then what was that?

6. What’s the best conspiracy theory you can make up on the spot?

7. Do you have any hidden talents?

8. What was the most embarrassing thing that ever happened to you?

9. What’s your most embarrassing moment?

10. Have you ever visited a palm reader and did he predict the right thing about your future?

11. What inedible thing do you wish you could eat?

12. Where is the craziest place you have danced?

13. Who would you rather hire: a personal chef, a personal trainer or housekeeper?

14. What is the worst lie you’ve ever told your parents?

15. What would you like to do if you could be a woman for a day?

16. What is the one movie that you have seen more times that you can count?

17. What’s the dumbest thing you’ve done?

18. If a movie is being made about your life, then which actor would play your role? Which actress would play your love interest?

19. What were you like in high school? What was your personality at that time?

20. If you got invited to lunch with a person who you have always wanted to meet then who is it?

21. Which one do you like the most: a summer house, a boat or a yearlong vacation?

22. When you were a child, did you realize that you are fitted in perfectly?

23. Which moments of your life do you cherish the most?

24. Have you ever regifted something that you received as a gift?

25. What was the best party you ever went to and why did you enjoy it the most?

26. What do you think about couples who are married but live in different areas or cities?

27. What do you think about the couple who own a business together and spend all their time at once?

28. Which of your personality characteristics would you like to change?

29. What fictional character do you relate to most of the time?

30. What’s the grossest thing you’ve drunk?

31. Which fictional villain made you feel real hatred towards them?

32. If you could get the first kiss with your celebrity crush in a movie, who would you do the kissing scene with?

33. What’s the most embarrassing thing you would willingly do for a million dollars?

34. If you can be born in a different decade, then which decade would you choose?

35. Have you ever pretended to speak a foreign language you don’t know?

36. How often do you go into a room and forget why you went into the room?

37. What’s the lamest thing you did to make your first crush notice you?

38. When you fall asleep, then what do you prefer to be chilled and warmed?

Deep Questions to Ask Your Crush Over Text

The key is to keep them interested, to leave them wanting more, and to do so in a way that allows them to figure you out. Doesn’t it sound complicated? It’s not. There are a few simple ways to start a discussion with your sweetheart. These deep questions to ask your crush over text show that it isn’t as difficult as it appears. ‎

1. Are you someone who likes to plan ahead or be spontaneous?

2. What’s one thing you think you spend way too much money on?

3. What will you choose between money and love? And why?

4. How do you imagine a completely perfect relationship? And why so?

5. What’s a compliment that you regularly receive?

6. Tell me about something you’ve never told anyone in your life.

7. What is the most ridiculous reason you’ve ever given for not going out?

8. What’s the one thing that drives you crazy about other people?

9. Does your name contain any specific meaning? If so, then what is it?

10. How do you cope with people that deliberately irritate you?

11. What was your luckiest moment in life?

12. Have you ever been unlucky in love? What went wrong?

13. What have you taken away from your previous relationship(s)?

14. Have you ever had a supernatural experience?

15. What’s something you’re looking forward to?

16. What is one thing that people believe you are but aren’t?

17. What is one of the most bizarre pick-up lines you’ve ever heard?

18. What’s the best compliment you’ve ever received?

19. What is the most nice thing that I ever said to you and you liked it the most?

20. What is something that your parents will be surprised to know about you?

21. Are there things you like about being single? Things you don’t like?

22. What is the most adventurous place you have visited and wanted to go there again?

23. Have you thought and are tired of making the first move to someone whom you liked?

24. Who’s a famous person you would definitely lose your cool around if you saw them on the street?

25. What’s something you consider a guilty pleasure?

26. Would you rather be known for being so smart or being so s#xy?

27. Are you a reserved person or do you express your feelings most of the time?

28. Do you believe in monogamy?

29. In what ways do you think we’re similar?

30. What is something that most people don’t know about you?

31. Do you have something that most people won’t believe about you if you told them?

32. What’s something you’ve done that you think everyone could benefit from trying?

33. How do you recharge — on your own, or around other people?

34. What’s something you like that people wouldn’t necessarily guess about you?

35. What’s the best new artist/song you’ve discovered recently?

36. What’s the worst date you’ve ever been on?

37. Do you volunteer anywhere?

38. What would you consider the No. 1 best movie of all time?

39. What are you proud of right now?

40. Are you someone who gets bored, or not really?

Deep Questions to Ask Your Crush While Texting

You’re probably already conversing online on a regular basis, and you’re flirting sporadically. Texting is an easy method to communicate, especially in the early stages. Intentional conversation starters foster intimacy while being engaging. Here are some deep questions to ask your crush while texting.

1. Would you rather date for money or for fame?

2. What is the craziest thing you’d wish to try out?

3. What is the one thing you admire about your parent’s relationship?

4. Would you rather date a younger or older person?

5. Have you ever smashed with a married woman knowingly?

6. What are some of the common lies married people tell?

7. What are some of the things you keep on lying to yourself about?

8. What do you consider boring when it comes to bedroom matters?

9. If you had to describe yourself in three words, which would you choose?

10. What is one thing people would never guess about you just by looking at you?

11. When was the last time you cried and why?

12. What are your thoughts about someone having a side chick?

13. What is the craziest adult movie you have ever watched?

14. Have you ever done it in someone’s house?

15. What is the one thing you could not live without?

16. Are you the type to plan everything or do you prefer to let things happen naturally?

17. How often should a dating person make out?

18. If your best friend cheats, would you cover up for them?

19. Have you ever lost a loved one? What did he look like?

20. What is the scariest thing that has happened to you as a child?

21. Which member of your family (close or less close) do you resemble the most?

22. What makes a good relationship go bad easily?

23. How do you know when it’s time to move on?

24. Who is the one person you are struggling to get out of your mind?

25. Should people take a break from relationships after a breakup?

26. What is the thing from your past that has marked your life the most?

27. Does your family influence your choice of partner?

28. Is it a good idea for people to be asking about others’ body counts when starting to date?

29. Have you ever moved in with someone before?

30. What do you think about a lady proposing?

31. What is the thing that attracts you most about the opposite s#x?

32. What are the top three qualities you look for in a potential conquest?

33. Would you rather talk dirty over a phone call or erotic chat over a text message?

34. What are your views on the materialistic types of relationships?

35. What is your no-go zone when it comes to bedroom matters?

36. What is the one thing that makes you decide to trust someone?

37. Have you ever been in love?

38. Is ghosting the best way to break up with someone?

39. What is your definition of a gentleman?

Deep Questions to Ask Your Crush in Person

Talking to your crush can be difficult, especially if you are reluctant or edgy. The more you flirt with your crush, though, the more confident you’ll feel in yourself and your flirting talents. It’s also a great way to let them know they’re on your mind! Here are some deep questions to ask your crush in person that may help you.

1. Have had to choose between two people at one point in your life?

2. Do you prefer to budget and stick to it or live from day to day?

3. What do you consider to be wasted money?

4. Have you ever regretted not letting someone know you like them?

5. How do you imagine your perfect life?

6. What do you get overly emotional about?

7. What event made you mature as a person the most?

8. What would it look like if you fully lived up to your potential?

9. Do you prefer to spend your life traveling or building a stable home?

10. If you were forced to move and go to an unfamiliar country, what things would you take with you?

11. What are the most common lies guys easily fall for?

12. Are you able to keep your anger under control?

13. What’s the best way to earn somebody’s respect?

14. How do you handle disagreements?

15. If you could only eat one dish for the rest of your life, which one would you choose?

16. If you were to lose one of your 5 senses, which one would you choose and why?

17. Who is one person you wish you could be?

18. What’s the hardest truth you’ve come to grips with?

19. What is best about your job?

20. Who do you look up to for relationship advice?

21. If you could make three wishes, which would it be?

22. What word describes you better than any other word?

23. What are you really obsessed about?

24. If tomorrow was your last day on earth, what would you do during those 24 hours?

25. What is the coldest place you have ever traveled to?

26. What is the scariest thing you have done?

27. Do you ever take part in any community service?

28. What are some of your ideas for how to keep a relationship strong over time?

29. Do you think men and women can be platonic friends?

30. What’s the most incredible thing you’ve ever eaten?

31. What is the thing that you are most grateful for?

32. What is your ideal work-life balance?

33. When you break up with someone, how do you do it?

34. What’s the worst breakup you’ve ever experienced? Why was it so bad?

35. What do you find strange that most people find normal?

36. Have you ever made a decision that changed your life completely? If yes, which one?

37. What is the one thing that allows you to relax when you are stressed?

38. What kind of trip would you like to take? Traveling to Maui for an all-inclusive resort, London for sightseeing, or Yosemite National Park for camping?

39. What has been the strangest conversation you have ever overheard? Do you remember the details?

40. What is the hobby that you always dreamed of practicing but never did?

Deep Questions to Ask Your Crush about Relationships

Are you seeking for some deep questions to ask your crush about relationships? The benefit of asking these questions is that they can lead to a range of outcomes. They may have a lot of fun, flaunt their attractiveness, or keep the conversation serious and intellectual. ‎

1. What do you consider a red flag in a relationship?

2. What is the most important thing in a relationship?

3. Do you think we are made for each other?

4. Do you think fights and jealousy are healthy components of a romantic relationship? Or do you think it should be avoided?

5. Do we communicate enough when we’re not together?

6. What is the best compliment I have given you?

7. Do you have a dream that I can help you achieve?

8. What’s the best and worst relationship advice you’ve ever gotten from someone? And from whom was it?

9. Before we even got together, have you thought about what it will be like to kiss me?

10. Which habit of yours do you think annoys me the most?

11. Mention a crazy thing you would want us to do?

12. What would be the worst thing I can do to make you want to end the relationship right away?

13. What song do you think best fits our relationship?

14. What is the one quality in me that you adore the most?

15. What do you value in a relationship?

16. What do you look forward to experiencing with me?

17. What famous real or fictional couple reminds you the most of us?

18. Do you think you act like a snob at times?

19. What is your favourite thing about me?

20. What do you think destroys most relationships?

21. Which day from our relationship would you choose if we could relive it?

22. What are your expectations for our relationship?

23. Were you nervous during our first kiss?

24. What do you feel makes a healthy relationship?

25. What is your favorite memory from our time together?

26. What do you like the most about spending time with me?

27. What do I mean to you?

28. If you could bring me to a place, you absolutely love, where would it be?

29. What’s something you used to believe about relationships but no longer do?

30. Would you surprise me with an expensive gift, or would you consult me before spending the money on it?

31. Do you like us holding hands or me holding close to your arm while walking?

32. What do you think you bring to our relationship? What about what I bring in our relationship?

33. What’s something I can do that will instantly make your mouth drop open and make you speechless?

34. How would you describe the feeling of being in a relationship with me?

35. What’s your favorite part of my body that you want to touch the most?

36. What do you think made me fall in love with you?

37. What is one thing I can do to improve our relationship?

38. What is a pastime or talent that you would like to learn as a couple?

39. What kind of clothing do you think I look the best in?

40. Would you rather take a bullet or kiss me all day?

41. What makes you super happy in our relationship?

42. Is there anything in our relationship that you think we need to work on?

43. Is there anything that you always wanted to tell but never got the guts to talk about?

44. Would you love it if I kissed you in public?

45. Where do I fit in in the next five years of your life?

46. How long did you think our relationship would last when we first started dating?

47. What am I doing that makes you feel valued?

48. If I get scared watching horror movies, would you hold me?

49. Can you tell me something that I texted you that made you smile?

50. What’s your favorite thing about our relationship?

Deep Questions to Ask Your Crush about Love

Here are some deep love questions to ask your crush. Just one inquiry at a time to your crush! The game might be one-sided, but you can participate as well. Back and forth with questions, or take turns answering all questions in a succession.

1. Have you been in love before? Who was your first love?

2. Do you think it’s possible to fall in love at first sight?

3. What is love to you?

4. Do you think people are made for each other?

5. Where is the perfect honeymoon locale?

6. How would you go about explaining what love is?

7. Describe the most romantic date you can think of — spare no expense!

8. When was the first time you said “I love you” to someone in your life other than family?

9. Do you remember our first date?

10. What should your ideal date wear for a dinner date?

11. Have you ever had a heartbreak?

12. What is the worst love kill for you?

13. What do you do when heartbroken to help you heal fast?

14. Have you ever fallen out of love? What happened?

15. What is your favorite song about love?

16. Would you rather love someone or be loved instead?

17. What will you go for between money and love?

18. What’s your love language?

19. What is your dream date night?

20. Would you love to live forever? Why?

21. What is the most beautiful thing in the world?

22. Have you ever had a dream you wished to not wake up from? What was the dream about?

23. Do you believe we can fall in love with someone for the rest of our lives?

24. Do you believe in true love or love at first sight?

25. When was the first time you were in love?

Deep Questions to Ask Your Crush to Get to Know Them

Are you actually prepared to escalate your conversation with your crush? First and foremost, examine the existing state of affairs. For example, are you certain that things have been going well? Do you have any evidence that your crush is also interested in you? If things are going strong use these deep questions to ask crush.

1. What do you do when you are in a happy mood?

2. What do you do when you feel sad?

3. What do you feel most proud of in your life?

4. Do men cheat more than women?

5. For you, what are the foundations of a perfect romantic relationship?

6. Are you the dominant or dominated gender?

7. Are you religious or spiritual in any way?

8. Do you believe in nicknames?

9. What’s your relationship like with your extended family?

10. What is your view on long-distance relationships?

11. How would someone get your special attention?

12. What do you think is your life’s purpose?

13. Do you believe in the existence of soulmates?

14. What do people underrate about you?

15. What characteristics do you admire (in self or others)?

16. Do you prefer to have money and influence over friends and being loved?

17. What passes as betrayal in a relationship?

18. Who is your favorite celebrity or who do you greatly look up to?

19. What’s one thing that you’ve never revealed to your dad or mom about?

20. What is the clearest sign that he loves you?

21. Do you have a hidden dream that you’ve never shared with anyone?

22. What do you fear most?

23. How do you know if someone is flirting with you?

24. What do you find yourself always procrastinating?

25. When was the last time you tried something new?

26. For you, what makes today worth living?

27. What’s your relationship to religion?

28. How do you find the strength to do what you know in your heart is right?

29. How have you changed in the last five years?

30. How would you describe ‘freedom’ in your own words?

31. How do you know when it’s time to continue holding on or time to let go?

32. What does home mean to you?

33. Is there ever a time when giving up makes sense?

34. What are you sure of in your life?

35. Are you extroverted or more introverted?

36. What happens when you are very mad at someone?

37. What are the three moral rules you will never break?

38. What are you looking forward to?

39. What do you feel you shouldn’t have done in your life?

40. What does it mean to allow another person to love you truly?

41. What has been the most terrifying moment of your life thus far?

42. What makes you smile the widest, even on sad days?

43. What would you wish to do but haven’t found an opportunity?

44. Can you hold on to one thing and say you are proud of it?

45. Do you get scared when you see your imaginations come into reality?

Deep Questions to Ask Your Crush to See if They Like You

Wooing someone is a time-consuming and exhausting process. However, if done properly, it can also be a lot of fun. Deep questions to ask your crush to see if they like you can assist you in wooing them, getting to know them better, and determining whether or not they like you. ‎

1. If I called you really late at night, would you answer?

2. What are your top three things to do on the weekend?

3. If you had all the time and money in the world, what are three things you want to do?

4. Do you prefer casual dating or long-term relationships?

5. What do you find most attractive in people?

6. What is the most pleasant thing someone can do for you?

7. What’s the biggest deal breaker on a date?

8. If you must dedicate a song to me, what would it be?

9. How can someone who likes you add value to your life?

10. What’s the most important thing in your life right now?

11. When you are having a bad day, what is the one thing that can turn things around?

12. What did you think of me the first time we met?

13. If you have the power to choose what I’m wearing right now, what would it be?

14. Would you rather date someone smart or hot?

15. How would you describe your ideal type in five words?

16. If you could dedicate a song to someone you love, what song would it be and why?

17. What’s the perfect way to ask someone out?

18. How do you know when you’ve fallen for someone?

19. Would you rather find the love of your life or be a millionaire?

20. What’s a gift you’ve always dreamed of receiving?

21. Have you ever experienced unrequited love?

22. Do you idealize your parent’s relationship?

23. What is the nicest thing someone could do for you?

24. If you can travel to the past? if so, then where do you want to travel?

25. What is your ideal dream location for a vacation to enjoy with your family?

26. What do you think about before you fall asleep?

27. If someone you liked didn’t like you back, what would you do?

28. What do you get nervous about the most?

29. What’s the kindest thing someone’s ever done for you?

30. Do you believe in soulmates?

Romantic and Deep Questions to Ask Your Crush

This section contains deep romantic questions to ask your crush. Before you ask them difficult questions like these, wait until you’ve gained their trust. ‎

1. If you could ask me one question, and I had to answer truthfully, what would you ask me?

2. Are you looking for something serious or casual right now?

3. Are your parents as attractive as you?

4. Are you looking for a relationship?

5. Is there anything you’re wondering about me?

6. Do you prefer cuddling or making out?

7. Do you shower at night or in the morning?

8. What is the most romantic thing you have ever done?

9. What is the perfect way to ask someone out?

10. Do you think tattoos are s#xy?

11. Where do you want to spend your life if you had to choose to stay in one place for the rest of your life?

12. If you get a chance to learn an instrument to play then which one would you like to play and why?

13. What is on your bucket list?

14. What’s the most impressive skill you have?

15. If I have to describe you in three words to my friend then what three words should I say?

16. When you are having a bad day then what usually cheers you up?

17. What’s the one thing that drives you crazy about other people? Why is that?

18. What are you looking for in a partner?

19. What is your preference – dating someone smart or hot?

20. What is your favorite place to go for a lunch meeting? Would you like to visit there with me? Which romantic music puts you in the mood there?

21. What should be the next romantic movie which you and I should watch out together?

22. What type of outfit would you like to see me wearing?

23. Which one is the most impactful and romantic book that you have ever read? Would you also recommend that book to me?

24. What is your most favorite memory of us together? And what about when we have been distant?

25. What was the first thought that popped into your mind when you met me?

26. If you could have a dinner date with anyone in the world, who would you choose?

27. What’s the type of person do you enjoy being around the most?

28. Is there anything that you want to change and evolve in our relationship?

29. Have you ever fantasized about me?

30. Which one of your parents do you find the most in your own personality?

31. Have you ever had s#x outdoors?

32. What turns you on?

33. Have you ever tried skinny dipping?

34. What would you like to do to me right now?

35. What would you want me to do to you right now?

36. What’s the naughtiest thing you have ever asked someone?

37. Which would you prefer – for people to see you as smart or sexy?

38. What’s your biggest and most secret fantasy?

39. What’s your favorite body part/feature on a girl/guy?

40. What’s your favorite type of foreplay?

41. If you were to choose a song you’ll have to listen to forever, what would it be?

42. Which part of my body would you want to kiss?

43. Would you like me to be naughty with you?

Intimate and Deep Questions to Ask Your Crush

Deep intimate questions to ask your crush are generally fine, if a touch edgy. To put it this way, you don’t want to come out as too sexual or curious. As a result, utilize these questions with caution. ‎

1. What method of orgasming with a partner do you find to be the most reliable?

2. What is sweeter between s#x and romance?

3. What is the craziest bedroom style you have thought of trying for a long time?

4. How many times would you have s#x in a week in an ideal world?

5. What’s something you’ve always wanted to try in bed but never got around to it?

6. What happened to your virginity?

7. When did you first get into the habit of masturbating?

8. Have you ever thought of someone else while making out?

9. What’s your most cherished s#xual fantasy? Do you think you’d do it in real life?

10. Outside of the bedroom, where do you prefer to have s#x?

11. Do you believe that s#xual compatibility or emotional compatibility is more important in a relationship?

12. What should someone do if they start catching feelings for their friend?

13. Have you ever been followed during a s#x session? Have you ever stepped into a room and found someone else there?

14. What is the most bizarre request you’ve ever received in bed? Are you the one who did it?

15. Can people date without s#x?

16. Do you want to be well-known? What do you mean by that?

17. What one attribute or ability would you get if you could wake up tomorrow with?

18. Which sexual position is your favorite? Which s#xual position is your least favorite?

19. What are the most sensitive erogenous zones on your body that don’t always get the attention they deserve? (Nipples, ears, neck, and so forth.)

20. Do you believe in staying friends with your exes? Why?

21. What’s the best pick-up line that you know?

22. Who would you like me to dress up as if we were going to role play?

23. Have you ever gone to a dominatrix? Would you ever go to one?

24. When you’re upset, where do you go?

25. What’s the most embarrassing item that you own?

26. What is the one addiction you are struggling with?

27. What’s the one s#x item you’ve been itching to try?

28. Have you ever smashed with your best friend’s partner?

29. When I come down on you, what do you appreciate the most?

30. What you ever had an encounter with a bedroom bully?

31. What is your worst s#x encounter story?

32. How long should normal s#x last?

33. What is the longest you have ever stayed without s#x?

34. How often should dating people make out?

35. What are your views on friends with benefits?

36. When you’re masturbating, what do you think about?

37. Would watching porn together turn you on?

38. Have you ever succeeded in getting someone pregnant? How did you deal with it?

39. What is one aspect of yourself that you wish you could change?

40. What do you think about a threesome?

Deep Personal Questions to Ask Your Crush

Let us now go through some deep personal questions to ask your crush. Go with the flow, but don’t be afraid to take risks! Every strong partnership starts with a risk. The more you learn about your crush, the more you will grasp what is and isn’t right for you. ‎

1. What movie would you consider your best ever?

2. What age do you consider the best in your life?

3. What city in the world do you find irresistible?

4. What is your preference between countryside life vs. busy fast-paced city life?

5. How much do you love news and current affairs updates?

6. Which section do you find yourself skipping to first in a newspaper?

7. What topics do you find most exciting in a discussion?

8. What age do you feel was the worst in your life?

9. What is your most frightening experience in life?

10. Where would you love to have your dinner date in town?

11. What rules define your life and daily living?

12. Do you feel you are living your dream like you wanted when you were a child?

13. What compliment do you receive most often?

14. What do you want to be remembered for?

15. What’s the hottest thing someone has ever done for you?

16. What do you find yourself spending money on without caring?

17. What’s something unexpected that you find attractive?

18. What makes you automatically swipe left on a person?

19. What rules do you have about dating?

20. What superpower would you choose if you had one?

21. Do you believe that flying or mind reading is a more useful ability?

22. What is your most common deal-breaker when it comes to dating?

23. What TV show do you often want not to miss?

24. Do you believe in fate controlling the outcomes in our lives?

25. What type of people do you enjoy hanging with the most?

26. What is beauty to you?

27. What does being a good person mean to you?

28. What is your take on religion?

29. What is your take on karma? (You get what you do to others in equal measure on earth)

30. What is your take on big parties vs. small in-house parties?

31. What are your daily routines in life?

32. What’s something you hate seeing other people do?

33. What issue in society makes you most angry?

34. What do you think about porn? Immoral or fine?

35. Which book would you suggest everyone read?

36. What motivates you to want to achieve your life goals?

37. Who in your life do you wish you met sooner?

38. What kinds of people do you simply not respect?

39. Do you think its mind over matter? Or matter over mind?

40. When last did you feel awe? What happened?

41. When do you feel you’re most confident?

42. Would you consider yourself naturally trusting or a more guarded person?

43. Do you fall in love easily?

44. What is your take on p#rn?

45. What is your take on s#x before marriage?

46. Are you a quantity or quality person when it comes to your friendships?

47. Do you think kindness should be applied to everyone or close friends only?

48. In relationships, are you someone who moves pretty quickly or takes things slow?

49. What’s your relationship to mental health like?

50. What one thing don’t most people know about you?

5 Tips for Choosing Deep Questions to Ask Your Crush

Now we are going to share with you some really useful tips that will help you know how to ask deep questions for your crush.

1. You’re still getting to know one another. Everything appears exhilarating, if not a bit terrifying. The good news is that by asking the right questions, you may easily elevate your connection.

But what are some deep questions to ask your crush over text? And how do you ask such inquiries without seeming annoying or strange? Some of the best questions to ask your crush include their feelings about certain romantic, sexual, or relationship-related themes. ‎

2. Do you know some deep questions to ask crush? These questions serve two purposes. For starters, they show that you are interested in their particular opinions. Second, they inform you about who they are, which may help you decide whether or not you want to pursue a relationship with them! ‎

3. When it comes to asking questions, be sure you’re doing so with genuine interest. You also don’t want to embarrass your crush, so ask these questions while you’re alone. ‎

4. You may also pose these questions to them when they are not expecting them. If you usually message at the same times every day, such as right after class or work, consider surprise them by chatting outside of those hours instead.

They may be surprised and wonder why, but if you play your cards well, they will appreciate it! ‎

5. Try to be flirty. Instead of asking boring questions, try something flirty and see how people react. Texting is an excellent method to get to know someone, so be creative. Make them laugh. Everyone appreciates being around someone who has a fantastic sense of humor, especially if they like them.

Final Thoughts on Deep Questions to Ask Your Crush

We hope you relished reading this assemblage of deep questions for your crush. Having a crush may be a thrilling experience. We’ve all had butterflies after watching their Instagram and TikTok postings.

You’ve probably already planned a slew of captions for when you make things official on social media. But before you get there, there are a few things you need to do, such as get to know them. LOL!

When you initially start chatting to your crush, you want to learn more about them in a way that distinguishes you from the other possible baes that continually send “WYD” and slide heart eye emoji in their dms all day.

Deep questions to ask your crush spark interesting, meaningful conversations that provide a peek of who they genuinely are. It might be puzzling to come up with deep questions to ask your crush that will keep your crush interested.

How many different questions can we ask regarding their favorite cuisine and color? That is when this list comes in helpful. So use it with caution.

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