100 Questions to Get to Know a Guy Better

Note: To make the most of these questions, adapt them based on your relationship with the guy, the setting, and your interests.

Fun and Lighthearted Questions

1. What’s the most embarrassing thing that’s happened to you?
2. If you could have any superpower, what would it be?
3. What’s your go-to karaoke song?
4. What’s the funniest movie you’ve ever seen?
5. If you could be any animal, what would you be and why?
6. What’s the most ridiculous thing you’ve ever believed?
7. What’s the best prank you’ve ever pulled or had pulled on you?
8. If you could time travel, where would you go?
9. What’s your favorite guilty pleasure?
10. What’s the most random fact you know?

Getting to Know Him Better

11. What are you passionate about?
12. What’s your biggest pet peeve?
13. What’s your biggest fear?
14. What’s your favorite childhood memory?
15. What’s your dream job?
16. What’s your biggest accomplishment?
17. What’s your biggest regret?
18. What’s your love language?
19. What’s your morning routine like?
20. What’s your evening routine like?

Deeper Conversations

21. What’s your philosophy on life?
22. What do you think is the meaning of life?
23. What’s your biggest life lesson?
24. How do you define success?
25. What’s your biggest challenge right now?
26. What makes you feel truly happy?
27. What makes you feel stressed?
28. How do you handle conflict?
29. What’s your opinion on relationships?
30. What are your values?

Fun Hypothetical Questions

31. If you could live anywhere in the world, where would it be?
32. If you could have dinner with anyone, dead or alive, who would it be?
33. If you could have any skill, what would it be?
34. If you could change one thing about the world, what would it be?
35. If you won the lottery, what would you do with the money?
36. If you could be invisible for a day, what would you do?
37. If you could switch lives with someone for a day, who would it be?
38. If you could have any job in the world, what would it be?
39. If you could travel back in time, where would you go?
40. If you could have any superpower for a week, what would it be?

Questions About Interests and Hobbies

41. What kind of music do you listen to?
42. What’s your favorite book?
43. What’s your favorite movie genre?
44. What do you like to do in your free time?
45. What’s your favorite hobby?
46. What’s your favorite sport?
47. Do you play any instruments?
48. Do you like to cook?
49. What kind of food do you like?
50. Do you like to travel?

Questions About Relationships and Love

51. What do you find attractive in a partner?
52. What’s your biggest turn-off in a partner?
53. What’s your ideal date night?
54. What’s the most romantic thing you’ve ever done?
55. What’s the most romantic thing someone has done for you?
56. Do you believe in love at first sight?
57. What’s your biggest relationship deal-breaker?
58. What’s your biggest fear in a relationship?
59. What do you think is the key to a successful relationship?
60. What’s the most important quality in a partner?

Questions About the Past and Future

61. What was your childhood like?
62. What were you like in high school?
63. What’s your biggest accomplishment so far?
64. What are your career goals?
65. Where do you see yourself in 5 years?
66. What’s your biggest dream in life?
67. What’s something you’re proud of?
68. What’s something you’re working on improving?
69. What’s something you’re excited about?
70. What’s something you’re grateful for?

Random and Fun Questions

71. If you could have any animal as a pet, what would it be?
72. What’s your favorite ice cream flavor?
73. What’s your favorite color?
74. What’s your favorite season?
75. What’s your favorite day of the week?
76. What’s your favorite holiday?
77. What’s your favorite thing to wear?
78. What’s your favorite drink?
79. What’s your favorite type of music to listen to while driving?
80. What’s your favorite thing to do on a rainy day?

More Deep Questions

81. What’s your biggest insecurity?
82. What’s your biggest challenge in life right now?
83. What’s something you’ve always wanted to try but haven’t?
84. What’s the best advice you’ve ever received?
85. What’s the worst advice you’ve ever received?
86. What’s something you’re passionate about that most people don’t know about?
87. What’s your biggest fear about the future?
88. What’s your biggest hope for the future?
89. What’s something you’re really good at?
90. What’s something you wish you were better at?

Fun and Flirty Questions

91. What do you find attractive in a woman?
92. What’s your biggest turn-on?
93. What’s the most romantic thing you can imagine doing?
94. What’s your favorite physical feature on a woman?
95. What do you think is the sexiest thing a woman can wear?
96. What’s your biggest fantasy?
97. What’s the most spontaneous thing you’ve ever done?
98. What’s your favorite compliment to receive?
99. What do you think is the most important quality in a partner?
100. What makes you blush?

Remember, the best questions are the ones that encourage open and honest conversation. Have fun and enjoy getting to know him better!