110+ Questions to Ask a Guy to Understand Him Better

Sometimes, getting to know someone feels like piecing together a beautiful, complicated puzzle… Each answer, each laugh, and each thoughtful pause gives you a new glimpse into who they are. 

Whether it’s over coffee, during a late-night drive, or in the quiet moments that feel just right, the right words can open doors you never knew existed.

These questionspark stories, reveal quirks, and uncover dreams; they bring you closer without even trying. That’s the magic of finding the perfect questions to ask a guy — it’s not about having all the answers, but about enjoying the journey together!

110+ interesting questions to ask a guy

Curiosity can be the spark that keeps conversations lively and meaningful! This list of interesting questions blends fun, thought-provoking, and lighthearted moments so you can discover new sides of his personality.

Whether you’re sharing laughs, swapping stories, or diving into deeper topics, these ideas make it easier to connect in a way that feels natural.  So, if you’ve been wondering which questions to ask a guy to keep things fresh, you’re in exactly the right place.

• Good questions to ask a guy you like

When you like someone, the right words can make all the difference! These good questions to ask a guy you like can spark genuine laughs, reveal shared values, and create those warm, unforgettable moments that bring you closer without forcing the conversation.

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 that 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 that 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 

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Getting to know someone goes beyond surface-level chatter—it’s about uncovering the stories, dreams, and experiences that make them who they are. If you’ve ever wondered what questions to ask a guy to truly understand him, this section is filled with thoughtful questions to ask a guy that open up real conversations.

26. Where would you like to travel the most, and why?
27. What is more intriguing to you? Unexplored depths 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 interesting questions to ask a guy that increase 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 have given to someone?
66. What is the best advice someone gave 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 a relationship?
72. What is an important quality that 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 were to 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?

• Fun questions to ask a guy

Finding the right words can turn an ordinary chat into something unforgettable. With thoughtful questions to ask a guy, you can uncover stories, spark laughter, and create moments that bring you closer without even trying.

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 that 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?
111. If you were a professional athlete, what sport would you choose and why?
112. If you could swap lives with a celebrity for a week, who would it be and what would you do?
113. What’s the weirdest food combination you secretly enjoy?
114. If your life had a theme song, what would it be and why?
115. What’s the most ridiculous dare you’ve ever completed?

How questions can strengthen a relationship

Asking the right questions isn’t just small talk—it’s a bridge to deeper understanding, trust, and connection. Whether you’re in a new relationship or years into one, curiosity can keep the bond alive and strong. When you know how to ask and listen, you make your partner feel valued, seen, and understood.

1. Builds emotional intimacy

When you ask meaningful questions, you open the door to deeper conversations that go beyond daily routines. Sharing hopes, fears, and personal experiences creates a safe space for vulnerability. Over time, these exchanges form emotional closeness that’s hard to break. 

Emotional intimacy helps couples feel more secure in their connection. Even a few well-chosen questions during the week can make a big difference in how connected you both feel.

2. Improves communication skills

Good questions encourage your partner to open up, which naturally improves the flow of conversation. Instead of assuming how they feel, you give them the space to share directly. This habit prevents misunderstandings and clears up confusion early. 

Over time, both partners learn to listen actively and respond thoughtfully. Strong communication is one of the biggest predictors of relationship success.

3. Shows genuine interest in each other

Taking the time to think about what questions to ask a guy—or anyone—shows that you truly care about their world. People naturally feel closer to those who make an effort to understand them. 

This genuine interest strengthens trust and makes your partner more likely to share in return. When both partners feel heard, it reinforces mutual respect. That, in turn, makes the relationship more fulfilling.

Watch this TED Talk by Joanne Davila, a psychology professor, who shares practical skills for building and maintaining healthy, fulfilling romantic relationships.

4. Encourages personal growth together

Asking thought-provoking or even challenging questions helps couples explore new ideas and perspectives. You might discover shared dreams or uncover differences that inspire growth. This habit can spark positive changes, whether it’s trying a new hobby together or adjusting how you handle challenges. 

Growth in a relationship means adapting while keeping your bond strong. It’s one way to ensure you’re both evolving in sync.

5. Keeps the relationship fresh and exciting

Over time, routines can make conversations predictable. Sprinkling in fun, surprising, or even slightly silly questions keeps things lively. Knowing a mix of good questions to ask a guy can lead to unexpected stories and shared laughter. 

These lighter moments are just as important as serious talks. They remind you both that relationships can be joyful as well as meaningful.

The bottom line

In the end, strong relationships are built on more than just shared routines—they thrive on curiosity, empathy, and the willingness to truly listen. Asking the right questions keeps your connection alive, helping you learn, grow, and laugh together. 

Whether you’re figuring out what questions to ask a guy early on or exploring deeper topics after years together, the goal is always the same: to understand and appreciate each other more fully. Keep the conversation flowing, and you’ll keep the bond between you just as strong.

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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