105 Questions to Ask a Guy by Phone or Face-to-Face

This blog post is all about questions to ask a guy.

Just being real here, it’s fair to say guys are so unlike women. And we are not talking anatomy here. Their ways of thinking and behaving could be strange. But sometimes guys are difficult to understand.

However, good communication is so important in any relationship. Just imagine a perfect world where you could ask questions and get flawless answers.

If only it were that easy. Men are much less complex than most women so it is important to be strategic and intentional with the questions you ask.

But no worries, we are here to help! In this blog post, you will find some awesome questions to ask a guy. We decided to categorize them from the friendship phase up to the fiance phase. Here at the 6 stages:

Basic Questions
Talking (Not Exclusive)
Dating
Official (A Couple)
Serious
Long-term

Basic Questions to Ask A Guy

Here are some good questions to ask a guy friend.

1 What animal would you say best describes you? Why?

2. What era would you travel back in time to? Why?

3. If you could take only three items with you to a deserted island what would they be?

4. If you had to choose to live without one of your senses which one would you give up?

5. If your life was based on a book or TV show or movie what would it be?

6. What are you looking forward to?

7. If you could eat one meal for the rest of your life what would it be?

8. What do you do to stay fit?

9. What was the best concert you’ve ever been to?

10. What is your favorite beverage?

11. At home do you wear slippers or go barefoot?

12. What is your favorite video game?

13. Do you have a nickname you like?

14. What’s your favorite Halloween costume?

15. What’s the longest period of time you’ve gone without sleep?

16. What’s your favorite radio station about driving?

17. How do you like your coffee?

18. What is your ideal breakfast?

19. Your least favorite fashion trend?

20. Can you remember the funniest thing you’ve ever done?

21. Where do you wanna travel this year?

22. What’s your favorite sport?

Questions to Ask a Guy When “talking”

Ya’ll not exclusive yet, but you could ask these to see where it goes. Here are some interesting questions that serve as great conversation starters.

23. Are you single?

24. What is your favorite movie?

25. What is a relationship big deal-breaker for you?

26. Or who is your celebrity crush?

27. What is your favorite thing to do in your free time?

28. What is your dream car?

29. What do you like to do on a rainy day?

30. What is a movie you hate but kept watching anyway?

31. If you could have a superpower what would it be?

32. Do you like chips if so what are your favorite chips?

33. What’s your favorite ice cream flavor?

34. Do you like a funny woman or a pretty woman?

35. Do you like to dance?

36. Who is your favorite rapper?

37. What is your pet peeve?

38. What is your favorite food?

39. What is your favorite social media platform?

40. Do you think all women are the same?

41. What is something you wish people better understood about you?

42. If you could be a location what location would you be?

43. Do you have any piercings?

44. Which fictional character do you relate to the most?

45. Could you date someone taller than you?

Questions to Ask a Guy When Dating

Such an exciting phase. Ask random questions for a deeper insight into your man.

46. What is your favorite romantic comedy?

47. What was the first thing you noticed about me?

48. If you didn’t have to work in life what would you spend your time doing?

49. What is your favorite way to celebrate your birthday?

50. What would be one meal you can eat every single day?

51. Do you want a future with me together?

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

53. Have you ever cheated on someone?

54. What attracted you to me?

55. What are your thoughts on polygamy?

56. What is something weird that you find attractive?

57. Did you wear a mask during the pandemic?

58. What are you looking for and what are your intentions?

59. How long was your last relationship?

60. How long ago did your last relationship end?

61. What are your top priorities in your life?

62. Would you ever consider driving _____ ? *say your least favorite car*

63. Would you ever paint your nails? Why or why not?

64. Could you tell me something on your bucket list this year?

65. If you could get the truth to one question, what would you ask?

66. Who do you look up to? And why?

67. Have you ever been in love?

69. Do you have siblings?

Questions to Ask a Guy when Officially in a Relationship

You both are finally a couple and exclusive. And your relationship status has changed. This is where you could ask a lot of fun questions.

70. Can you teach me something you know how to do well?

71. What is your favorite childhood memory?

72. Do you care what my feet look like?

73. What would you so with a million dollars?

74. Can money buy you happiness?

75. What are three things you wish you could tell your younger self?

76. What are you investing in right now?

77. Who knows you the best?

78. What quality are you most attracted to in a partner?

79. How is your relationship with your family?

80. What do you love about your best friend?

81. Have you ever been caught in your birthday suit accidentally?

82. Do you think getting kicked in the balls hurts more than childbirth?

83. What is something you will never sacrifice?

84. What are you most ashamed of?

85. What is your love language?

86. Have you ever skinny dipped?

87. What is the best gift you’ve ever received and who was it from?

Questions to Ask a Guy When in a Serious Relationship

Questions to Ask a Guy Serious Relationship

If you want to take things to the next level, it would be a good idea to ask him these important questions. Deep questions that will make your bond even stronger.

88. Can I meet your friends?

89. Would you like to meet my friends?

90. Do you want kids if so, how many?

91. How would you describe me to others?

92. What is your financial situation?

93. What are you insecure about?

94. What thing about “us” do you love the most?

95. How is your mental health?

96. What is your toxic trait?

97. Why do you treat me the way you do?

98. What are your spiritual beliefs?

99. What holiday traditions are important to you?