300+ Best Questions To Ask A Guy (Or Your Boyfriend/Crush)

Sometimes when you are talking to a guy, you end up running out of ideas to talk to him and all you are left with is asking ‘what’s up’ or ‘how you doing?’.

If you are in a similar situation and looking for ideas on questions to ask a guy, here are some great set of questions that will help you in get to know him better.

Getting inside a man’s brain can be hard work. Often women resort to several tactics to find out what’s inside their brain. But the simplest way to do it is by asking the right questions.

But you need to remember that every guy is different. So choose the right question that works best for you. You will be surprised to see which questions will get his interest. Even if some questions might not interest him, it’s worth a shot.

Before I start, make sure to ask follow up questions whenever necessary so that your conversations will be much more interesting and you will make the most out of it.

20 Questions To Ask A Guy [Or Boyfriend/Crush]

1. What are you most excited about when you wake up in the morning?

2. Tell me about some of your hidden talents?

3. Can you describe yourself in 3 words?

4. What are your personal/professional goals?

5. How do you spend your weekends?

6. Is there any one thing that you like most about me?

7. Can you tell me about your childhood life?

8. Is there anything that you are insecure about?

9. What according to you is an ideal love relationship?

10. If you get a chance live as a fictional character – who would it be?

11. Can you describe me in 3 words?

12. Do you listen to your heart or your brain?

13. Are you a spiritual or religious person?

14. What is your biggest regret?

15.  What is the ideal dream date according to you?

16. Is there any of your accomplishment that you are very proud of?

17. What are you most passionate about?

18. What is your biggest regret?

19. What kind of TV shows do you love watching?

20. What are the qualities in a person that attract you the most?

20 Funny Questions To Ask A Guy[Or Boyfriend/Crush]

1. Do you consider cereal a soup? Why?

2. If you get a chance to start a secret conspiracy, what would it be?

3. When did you had your first kiss and with whom?

4. Are you a naughty person?

5. Is there any food that you can eat everyday and not get bored?

6. Is there any funny childhood memory that you can share with me?

7. Imagine you are a waiter and you get a customer who is a jerk. Would you spit in their food?

8. Which animal is the cutest in the world according to you?

9. If you get a chance to act as a comic character, who would it be?

10. Can you share the most ridiculous fact that you have heard of?

11. Do you consider hot dog a sandwich? Why?

12. Best Wi-Fi name you have ever seen?

13. If you can be invisible what is the first thing you would do?

14. Funniest joke you have ever heard of?

15. Do you get scared watching horror movies?

16. If you were a mad scientist, what would you invent?

17. If animals can talk, who would be the rudest according to you?

18. What is the secret superpower you wish to have?

19. If the police arrest you for no reason, what would your friends assume you have done?

20. What is the most embarrassing thing you have ever done?

20 Flirty Questions To Ask A Guy And Drive Him Crazy[Or Boyfriend/Crush]

1. How are you still single? (if he is still single)

2. What is your favorite nick name?

3. If you can describe me in one word what would that be?

4. What are the ideal qualities that you look in a girl?

5. What kind of boyfriend you would like to be?

6. How did you become so hot/handsome/cute?

7. Which is the sexiest scene you like from a movie?

8. What is your favorite physical feature in a girl?

9. What is the perfect first kiss according to you?

10. Am I your type?

11.  What is your ideal first date?

12. What features turn on you the most?

13. Is there any outfit that you would love to see me in?

14. Will you love/hate it if I put my hands under your shirt?

15. Tell me about your biggest fantasy?

16. Do you like it if I talk dirty?

17. Did you have any flirty dreams about me? What is the most exotic dream you have ever had?

18. Can you guess the color of the underwear I’m wearing right now?

19. Do you have any favorite place where you would like to make out?

20. What did you feel when you first saw me?

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20 Good Questions To Ask A Guy[Or Boyfriend/Crush]

1. What makes you smile no matter what?

2. What is the one thing that you are most proud of?

3. What is the most scariest thing you have ever done?

4. Is there anything that you fear the most?

5. What is the thing that you are most thankful for?

6. Is there any movie that you can watch your whole life and not get bored?

7. Is there any secret you can share with me that you haven’t shared with anyone else?

8. Are you a cat person or a dog person?

9. Is there any country where you would love to settle down?

10. Who is the closest person in your family and why?

11. Do you love ice cream? What is your favorite flavor?

12. Tell me about your family?

13. What is the stupidest thing you have ever done?

14. If you can rewrite your past what would you like to change?

15. Is there any fictional/historical person you would love to be?

16. What is your best feature according to you?

17. What is the hardest thing physically/mentally you have ever done?

18. How do other people describe you?

19. If you are provided with three wishes, what would they be?

20. If you win a million dollar where would you spend it?

20 Deep Questions To Ask A Guy[Or Boyfriend/Crush]

1. Is the anything about you that you would like to change?

2. Are you a spiritual or religious person?

3. Are you an introvert or extrovert person?

4. Are you closer to your mom or dad? Why?

5. What is the best/worst phase of your life?

6. What are your thoughts about sharing your password with your partner?

7. If you would like to ask me one question that I have to answer truthfully, what would that be?

8. Would you like to live for 100 boring years or 50 adventure filled life?

9. Is there anything that you would sacrifice for a stranger?

10. What is your best memory with your parents?

11. Are there any of your priorities that has changed over time?

12. What was the best day of your life?

13. What was the best lesson that you learned from your parents?

14. Is there any memory in your life that makes you smile instantly?

15. What is a meaningful life according to you? Are you living it right now?

16. What would you like your final words to be?

17. What according to you is the most beautiful thing in the world?

18. Do you believe in God, Heaven and Hell?

19. Do you believe in true love?

20. What is the nicest thing anyone has done for you?

20 Personal Questions To Ask A Guy[Or Boyfriend/Crush]

1. Do you like spending time with your partner, friends or family? Why?

2. What activity makes you feel at peace?

3. If a homeless person asks you for money, will you give them?

4. What according to you is waste of money?

5. Is there anyone who you look up to and want to be more like them?

6. What are your biggest life goals? How much have you achieved them?

7. Have you learnt any lesson in life the hard way?

8. Is there anything that you would like to get off of your cheat?

9. Do you face your fears or run away from them?

10. Is there any place you love to go when you want to be alone?

11. Do you love nature, beaches or mountains?

12. Which is your favorite honeymoon destination?

13. Do you have any phobias?

14. Who is the most important person in your life?

15. Do you have any controversial opinion?

16. Is the anything that seemed normal in your family when you were growing up but feels weird now?

17. How political are you?

18. Is there any part of your personality that you would like to improve?

19. How adventurous are you?

20. Are you a shy person?

20 Serious Questions To Ask A Guy[Or Boyfriend/Crush]

1. What according to you is the biggest problem in our world today? And what should people do about it?

2. Is there any person in the world (living or dead) with whom you would love to have lunch with?

3. What are your principles and morals in life?

4. Do you prefer going out alone with your partner or as a group?

5. Were you in love with anyone before? If yes, how many times?

6. Are you still in touch with your ex?

7. Do you judge a person before you even know them or would you like to know about them first before judging them?

8. Do you look for motivation in your inner self or elsewhere?

9. Is there anything that is a must for you to start your day?

10. If my bestie made a move on you, what would you do?

11. What experiences made you a better person that you are today?

12. What is a perfect life according to you?

13. Is there anything that you have done in the past which you still regret?

14. How do you deal with disagreements with friends/family?

15. What was your first impression about me?

16. What are your thoughts about having kids?

17. What are your thoughts about saving money?

18. How is your relationship with your parents/siblings?

19. Do you have any career goal? What have you been doing to achieve it?

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20. What are your financial plans for the future?

20 Interesting And Fun Questions To Ask A Guy[Or Boyfriend/Crush]

1. Do you like to be famous? For what reason?

2. What is the worst advice that you have ever received?

3. Tell me about your funniest dream?

4. Have you ever tried wearing a girl’s clothes?

5. What is the funniest thing that has ever happened to you?

6. Any funny incident where you were caught doing something?

7. Were you ever hit by a girl/guy?

 8. When was the last time you washed the dishes?

9. Which superhero would you love to be and why?

10. What is the first thing you do in the morning?

11. Which animal represents you the best? Why?

12. What are your views about giving second chances?

13. Did you do anything embarrassing when you are drunk?

14. List any three things that you have never done but would like to do?

15. Do you have a tattoo? Where?

16. Do you believe in aliens?

17. Which is the most terrible movie you have ever watched?

18. Would you like to play role in any movie? Which one?

19. What weapons would you like to have if there was a zombie apocalypse?

20. If you get a chance to date a celebrity who would that be? Why?

20 Cute Questions To Ask A Guy[Or Boyfriend/Crush]

1. What do you consider an ideal date activity? (romantic/sporty/adventure)

2. Best thing that has ever happened to you?

3. The person you most admire?

4. What are the simple things that make you smile?

5. Attractive quality of a person according to you?

6. Tell me about your first crush?

7. What is your most favorite song?

8. What is the best part of a relationship according to you?

9. Deep down are you a soft person?

10. What are your favorite hobbies?

11. What impresses you the most about a girl?

12. What is the first thing that you notice in a girl when you meet her?

13. What is the craziest thing you have ever done?

14. Did you have any high school crush?

15. With whom you love to hang out more often?

16. Is there any movie that made you cry?

17. Which is your favorite food? Cuisine?

18. Which is your favorite sport?

19. Imagine we are a couple – how will you celebrate our first anniversary?

20. Do you believe in love at first sight?

20 Weird Questions To Ask A Guy[Or Boyfriend/Crush]

1. Who is person who is always in your missed calls?

2. Are you wearing pajamas or shorts? Which color?

3. Do you talk to your pets?

4. If you have the power to build your own country what is the first rule you will put in place?

5. Name a game which you dominate?

6. If you get the opportunity to create your own TV show what would you name it?

7. If you see a ghost that wants to play with you what would you do?

8. If aliens come to abduct you – would you fight back or go with them?

9. Is there anyone you would like to punch in the face?

10. What is the toughest decision you ever had to make?

11. Do you always look yourself in the mirror?

12. What makes you feel good?

13. Ever had a crush on a guy?

14. Do you workout? What’s your favorite exercise?

15. If you had the option to be anyone for one day, who would you want to be?

16. Who is friendlier? Pets or humans?

17. Did you ever cry watching a TV show or movie?

 18. Which person are you thinking about right now?

19. Which is your favorite color?

20. Have you ever danced in the rain?

20 Questions To Ask A Guy You Just Met

1. Tell in three words how your friends would describe you?

2. What would you be doing if you weren’t dating right now?

3. Who is your favorite family member and why?

4. Whom do you look up to the most?

5. What is your most memorable incident from childhood?

6. Is there anything that other people can’t tell about you by looking at you?

7. Which is your favorite movie genre?

8. Tell me about your hidden talents?

9. Which is the most frightening moment in your life?

10. Did you ever have a heart break? How did it change you?

11. What are you most passionate about?

12. Do you have pets at home?

13. What scares you the most?

14. Did you ever steal anything?

15. Do you support gender equality or are you against it?

16. What is love according to you?

17. Is there anything that you are scared of?

18. If you wake up tomorrow as a girl what would you do?

19. Which the most amazing place you have ever visited?

20. What is your first impression about me?

Bonus Random Questions To Ask A Guy[Or Boyfriend/Crush]

1. What is your favorite book?

2. What according to you is the best sign that you have chemistry with someone?

3. What do you like to do in your free time?

4. Who was your favorite teacher in school?

5. Do you like small talk or long talk?

6. Do you like to go on ling rides?

7. Best compliment you have ever received?

8. What are your thoughts about splitting bill during a date?

9. How do you unwind after a long day?

10. Strangest situation you have ever found yourself in?

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11. Do you like dancing?

12. You favorite type of clothing?

13. Most fun you have ever had?

14. What annoys you the most?

15. Is there anyone who knows all your secrets?

16. Your celebrity crush?

17. Your favorite quote?

18. Is there anything that gave up for love?

19. What do you have to say about public display of affection?

20. Your favorite childhood memory?

21. Is there anything that you are jealous of?

22. Do you love playing video games?

23. What are your biggest weaknesses?

24. Is it better listening to heart or brain?

25. Would you like to live country side or in a big city?

26. Is there any dream job that you would love to do?

27. Have you ever got in trouble with the law?

28. Did you like to keep yourself updated with the latest news or do you not care?

29. Your biggest regret so far?

30. Where do you see yourself in the next 5 years?

31. What would you like to be, smart or happy? Why?

32. Has anyone seen you naked?

33. Do you like waking up early or late?

34. Do you believe in previous life? If yes do you think we have met in previous life?

35. Are you naughty or nice?

36. Who is your celebrity crush?

37. If you had the power to read someone’s mind, who would it be?

38. Did you ever cheat during exams in school/college?

39. Your favorite nick name?

40. Did you ever smell your socks?

41. 40 years from now what will you be nostalgic about?

42. What came first, chicken or egg?

43. Ever wished you had an extra body part? What is that and why?

44. Weirdest thing you have ever done at home?

45. Is there anything you want to completely remove from existence?

46. What are some of the funniest nicknames you have made up?

47. What do you find attractive in women?

48. Describe yourself in one word?

49. Do you have a bucket list? Can you share them with me?

50. Do you like Facebook or Instagram?

51. Do you believe in Government conspiracies?

52. Your favorite place where you would like to live in?

53. Have you done any brave thing that you are proud of?

54. What makes you happy?

55. Best compliment you have ever received?

56. Who is your best friend and why?

57. Is there any decision you made that changed your entire life?

58. Is there anything you want to do before you die?

59. Your all time favorite movies?

60. If you were held at gun point and were told that if you didn’t entertain them then you will die, what would you do to impress them?

61. If you had a time machine would you like to go in the past or the future?

62. Would you like to go on a space trip?

63. Is there anything that you believe in that most people don’t?

64. Did you learn anything new this week?

65. Do you have any piece of advice that you want everyone to follow?

66. Is there any wild animal that you would like to have as a pet?

67. Do you prefer romantic candle light dinner at home or a fancy restaurant?

68. How old were you when you had your first kiss?

69. Did you have a hard childhood life?

70. Are you superstitious about anything?

71. What is your life goal at the moment?

72. If you win a trip to go anywhere in the world, where would you like to go?

73. If you met our resident randomly, what would you say him?

74. If you had to choose clothes for me what would it be?

75. Which is the cutest animal in the planet according to you?

76. Is the any food you can eat for the rest of your life and never get bored?

77. Would you like to be rich or famous?

78. What would you rather choose – peace and happiness or $10 million?

79. How do you imagine a perfect relationship?

80. What is your secret guilty pleasure?

81. Is there any one thing you can’t live without?

82. Are you a morning person or night person?

83. What clothes do you wear when you go to sleep?

84. What turns you on?

85. Have you ever lied to you parents that you regret about?

86. If you had a chance to rename yourself, what name would you like to choose?

87. Is there anything that you wish to be better at?

88. Has anyone cheated on you?

89. Most spontaneous thing that you have ever done?

90. What annoys you the most?

91. Favorite thing to do with your family?

92. Who was your first crush?

93. What according to you is the most romantic thing to do on a date?

94. What is your favorite sport?

95. What is your favorite place to hang out?

96. Do you love home food or junk food?

97. Did you know that I like you?

98. Tell me about the last dream that you remember?

99. Would you sacrifice your life for someone you love?

100. Do you think I can be your ideal girlfriend?

The next time you run out of ideas on questions to ask a guy, I hope you will remember this article and get ideas for questions to ask him.

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