11 Questions to Ask a Guy to Understand Him Better

Conversations don’t always come easily, especially if we are dating a partner who is shy and closed off.

Whether you are on a first date and trying to remember some questions to ask a guy or are already in a relationship with them, well-selected questions to get to know a guy can get you through a rough patch of silence.

Questions to ask a guy are best when combined with a comfortable atmosphere and the right moment. Funny, random questions to ask a guy can be useful almost anytime, yet the emotional and thought-provoking ones should be used carefully.

Think of the setting when picking questions to ask a guy.

111 interesting questions to ask a guy

Getting to know someone on a deeper level can be an exciting journey filled with discovery and connection. To help you navigate that path, here are some thought-provoking questions. 

From their passions and dreams to their favorite books and travel experiences, these questions will unravel the layers and reveal the true essence of a person. So, let’s embark on this adventure of understanding and forging meaningful connections through questions that will solve your query about “What questions to ask a guy?”

Good questions to ask a guy you like

When entering a new relationship, we want to learn more about our partner, their dreams, hopes, and flaws.

The right questions to ask someone to get to know them will get us useful answers sooner. Rely on these questions to start and build your repertoire of things to ask a boy.

1. What is the habit you have that makes you unique?
2. What is a habit of others that crazily annoys you? 
3. What is a habit you have you believe someone would be annoyed by?
4. What is your favorite movie of all time?
5. What do you find is a complete waste of time?
6. What would your perfect date look like?
7. What is your favorite book which you have read in one sitting?
8. What is the silliest entertainment you enjoy?
9. What is your favorite video game genre?
10. What is the song you love the most?
11. What is the song that annoys you the most?
12. What kind of student were you?
13. What is your favorite student memory?
14. What are you too hard on yourself for?
15. What was your favorite subject in school?
16. Do you have any brothers or sisters?
17. What did your first crush look like?
18. Do you like sports? Which one is your favorite, and why?
19. What is your favorite scent?
20. Have you ever sung in public? If not, would you be willing to?
21. Did you ever participate in a protest?
22. Were you ever in a fistfight?
23. What is your favorite band?
24. Do you own a nice suit?
25. What’s something you’re currently learning or interested in learning?

Questions to ask a guy to get to know him 

Your collection should encompass both questions to ask a boy to get to know him and funny questions to ask a guy. When they feel they are on the spot, they might put up a wall and close off.

Therefore, when things become too serious or deep, use lighter, flirty questions to ask a guy and prevent them from closing up emotionally or conversationally.

26. Where would you like to travel the most, and why?
27. What is more intriguing to you? Unexplored depth of oceans or the unreachable vastness of the universe?
28. What is the manliest thing you have ever done?
29. What is the least manly thing you have ever done?
30. What movie or book villain made you hate it? 
31. If money were no issue, what would your life be like?
32. If you were able to design your amusement park, what would it look like?
33. If you could leave everything for a month and plan a road trip, where would you go?
34. Are there names that are ruined for you because of someone horrible you knew?
35. If coffee is illegal, how would it be called in the black market?
36. If you woke up as a girl one day, what would be the first thing you’d do?
37. Imagine your life is a reality show; how would you name it?
38. What is the worst dream you have ever had?
39. What is the most pleasant dream you have ever had?
40. If machines were to take over the world, how do you think the world would look?
41. What is the saddest movie you have ever watched that you will never watch again?
42. What would your friends say about you?
43. What is the craziest thing you’ve ever done?
44. Are you a coffee or tea person?
45. What’s your favorite way to spend a weekend?

Random questions to ask a guy

At the beginning of a relationship, we all wonder what to talk about with a guy so we get to know them better and become more intimate.

If you are wondering what are interesting questions to ask a guy that increases connection, check out our selection of good questions to ask a guy to grow closer.

46. What is the kindest thing someone has done for you and vice versa?
47. What is something you would like to do but will never do?
48. What makes you angrier than it should be?
49. What do you feel about pets? What is your favorite pet?
50. What makes you different from other people?
51. What makes you nervous?
52. What would be your absolute perfect day?
53. What is the best mistake you have ever made? A mistake that turned out well.
54. If you could pause time, what would you do?
55. What is the biggest life lesson you learned the hard way?
56. Would you willingly go to the deserted island?
57. What would you take with you on a deserted island?
58. How would you spend your time if you knew you had a month more to live?
59. What is the worst job you have ever had?
60. What is your dream job?
61. If you had to be born somewhere else, where would that be?
62. What makes you laugh uncontrollably?
63. What is your favorite hobby?
64. What helps you chill and unwind at the end of a stressful day?
65. What is the best advice you gave to someone?
66. What is the best advice someone gave to you?

Meaningful questions to ask a guy you like

The best questions to ask a guy are meaningful yet simple. They invite them to share and are open-ended. Some can also work as questions to ask a guy over text, but if you wish to start a significant discussion, we propose you do it in person.

The best questions to get to know someone are created amid conversations based on mutual sharing.

67. What did you learn a little too late?
68. What is the most important thing you have learned so far?
69. What are your favorite childhood memories?
70. What pushes your buttons the most? 
71. What is your most important rule in the relationship?
72. What is an important quality which you believe your partner should possess?
73. What are the things you think a girl should know before starting to date you?
74. What do you make of psychology, and what impact do you think it has on everyday life?
75. How do you see yourself in 20 years?
76. What is the most romantic thing you’d do if time, space, or money were not an issue?
77. If you could go back in time, is there anything you would say to your younger self?
78. If you could go to any period in history, which period would that be?
79. Do you believe in miracles?
80. What is the price you would be willing to pay to stay forever young?
81. Are you rather a morning bird or a night owl?
82. Do you have a role model? Someone you’ve been looking up to?
83. If you would make a character or a mental change in yourself, what would it be?
84. If you could change one thing about the world, what would it be?
85. What do you think is better, to be born good or to overcome your evil nature through great effort?
86. What’s the best piece of advice you’ve ever received, and who gave it to you?

Watch this video to learn how to set the pace in a relationship without scaring someone away:

Fun questions to ask a guy

When we want to learn about what our partner thinks of us and our relationship, we feel a bit scared and seem to lack the right words.

This is a great opportunity to rely on existing relationship questions to ask a guy. Customize them when needed to increase to maximize openness.

87. How and when did you realize you like me?
88. What is one difference between the two of us you love?
89. What is one difference between us you hate? What is your favorite sex position?
90. Do you like to cuddle?
91. Where do you like to kiss the most?
92. Where do you like to be kissed the most?
93. What does your bedroom playlist look like?
94. Do you prefer to be on the top or the bottom?
95. Do you picture me naked?
96. What was your first impression of me?
97. How would you describe our first kiss?
98. What do you remember the most from the first day we met?
99. If I had to move to a country far away, would you go with me?
100. If you could change one thing in your relationship, what would it be?
101. What is that one secret you always wanted to tell me but never did?
102. What are the perks of a single life?
103. What are the perks of partnership?
104. What’s your go-to karaoke song, and why?
105. If you could time travel, which era or time period would you visit and why?
106. What’s the most unusual pet you’ve ever had or would like to have?
107. What’s the most memorable road trip you’ve been on, and where did you go?
108. If you were to create your own ice cream flavor, what would it be called, and what ingredients would it have?
109. What’s the funniest or most embarrassing thing that has ever happened to you in public?
110. If you could have any superpower, what would it be, and how would you use it?

If you were a professional athlete, what sport would you choose and why?

Final thoughts 

We all feel stuck in a conversation sometimes. Having the right questions to ask a guy can start an interesting discussion and help us better understand our partner.

Stimulating conversations and thought-provoking questions can increase the bond between you.

When contemplating what to ask, be mindful of the environment too. Some of the questions to ask a guy can be emotionally charged, and if you want them to share, make sure the environment is right.

Moreover, feel free to play and customize the questions to maximize sharing and bonding.

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Milica Markovic Other

Milica Markovic has graduated from the Faculty of Philosophy with a degree in Clinical Psychology. She has 7 years (and counting) of Psychotherapy and Coaching education (both Transactional Analysis and Psychology of Personal Constructs) and experience in working with clients. Throughout her career,... Read more she has had remote clients around the world facing various personal, academic, or professional challenges. She finds her primary duty is to establish a trusting environment in which clients can feel safe enough to discuss anything that might be troubling them and grow closer to their goals. She believes that whether you are experiencing a personal, relationship related, or professional challenge, the journey to surpassing it can be made easier with the right help by your side. Milica is also a strong advocate of lifelong learning and continuous improvement. Read less