100 Good Questions To Ask A Guy

Meeting a guy you like and effortlessly clicking with them is a refreshing experience. The conversation flows seamlessly, everything feels natural, and time seems to fly. On the flip side, there are situations where, despite the desire to connect, interactions feel stiff—especially when dealing with individuals like a hard-to-impress mother-in-law. Fortunately, there are expert-approved techniques to elevate your conversation skills.

Starting with “breadth questions” serves as an excellent entry point to transition from awkward small talk to more comfortable and genuine discussions. These questions can delve into various aspects of his life, such as his family or career.

Tamekis Williams, LCSW, founder of Mission Dorothy Female Empowerment Services, advises steering clear of “yes” or “no” questions and opting for open-ended ones instead. Questions that explore his inner world, such as his thoughts, goals, and dreams, contribute to strengthening the bond between individuals. Orbuch emphasizes that sharing personal information enhances any relationship, and deeper questions facilitate meaningful self-disclosure.

Williams highlights the importance of creating an inviting and warm atmosphere when initially meeting someone, allowing the other person to feel comfortable opening up. It’s crucial to be mindful of the approach, choosing questions that are not critical or invasive. Depending on the individual, topics like political and religious beliefs might be best avoided initially.

To encourage someone to open up, taking the lead in sharing a bit of vulnerability can be effective. By answering questions about yourself while asking about the other person, you create a conducive environment for genuine and meaningful conversations. For instance, sharing a personal experience like moving to a new place and expressing affection for your community can prompt the other person to share their experiences and feelings.

We have packaged 100 good questions to ask a guy you like and get to know;

  1. How do you prefer to unwind on your days off?
  2. What genre of music resonates with you?
  3. Reflecting on past travels, what stands out as your most memorable vacation and why?
  4. What destination is at the top of your travel wishlist, and what draws you to it?
  5. Can you share your hobbies and the story behind how you developed an interest in them?
  6. Looking back, which age holds the fondest memories for you during your childhood?
  7. Engaging with literature, what was the latest book or article you enjoyed?
  8. In social settings, do you find yourself leaning more towards extroversion or introversion?
  9. Share your thoughts on the most recent series you indulged in during a binge-watching session.

10. Are you a fan of podcasts, or do you predominantly enjoy music in your leisure time?

11. Express your sentiments about holidays—do you have a favorite, and if so, what makes it special?

12. If you had to stick to one type of cuisine for the rest of your life, what would it be?

13. When it comes to entertainment, do you prefer the cinema experience or watching movies at home?

14. Everyone has a guilty pleasure; what’s yours?

15. Can you recall the age when you experienced your first celebrity crush, and who was the fortunate celebrity?

16. Is there something specific that has the power to instantly brighten your day?

17. Are there any particular habits or behaviors that irk you as pet peeves?

18. Among the three main meals—breakfast, lunch, and dinner—which one holds the title of your favorite?

19. Is there a song that never fails to lure you onto the dance floor?

20. When seeking immediate tranquility, which activity serves as your instant calming ritual?

21. In an ideal scenario, how would you choose to celebrate your birthday?

22. How do you typically occupy yourself during your daily commute to and from work?

23. Considering the four seasons, which one stands as your favorite, and what makes it special?

24. Which phone app sees the most frequent use in your daily life?

25. When it comes to meals, do you prefer cooking at home or ordering in?

26. In the realm of board games, do you have a favorite that you enjoy playing?

27. How do you take your coffee—black, with milk, or perhaps with a special twist?

28. Reflecting on your possessions, is there one item that holds particular sentimental value, and why?

29. Imagining a lottery win, what would be the initial action you take?

30. During your alone time, what activities bring you the most enjoyment?

31. Can you recall the most memorable concert you’ve ever attended?

32. In terms of physical activity, do you have a preferred type of exercise?

33. Which causes or social issues are particularly meaningful to you?

34. In the realm of entertainment, do you have a preferred content genre, such as horror, sci-fi, or rom-com?

35. Can you share an integral aspect of your daily routine that you consider essential?

36. Reflecting on gifts, can you recall the least favorable gift you’ve ever received, and how did you handle the situation?

37. Is there a person or something specific that consistently brings laughter into your life?

38. When it comes to activities, do you enjoy group engagements, or do you prefer solitary pursuits?

39. Describing your ideal scenario, what would a perfect first date look like for you?

40. If you could paint a picture of your perfect day, what elements would it include?

41. Do you have a penchant for collecting anything specific or unique?

42. On a positive note, can you share the story behind the best gift you’ve ever received and why it holds significance?

43. Imagining an ideal culinary experience, how would your perfect meal be composed?

44. Are there any podcasts that you particularly enjoy and would consider your favorite?

45. Is there a specific job or profession that you would unequivocally rule out?

46. Upon returning home from work, what’s the initial activity you typically engage in?

47. Who or what serves as a source of inspiration for you in your professional journey?

48. When it comes to taking time off from work, what approach do you generally follow?

49. Can you share an aspect of your industry that might not be evident to someone on the outside?

50. Is a morning routine part of your workday, and if so, could you provide insights into what it entails?

51. In your current position, do you have the flexibility to work remotely, and if yes, do you find it enjoyable?

52. Regarding your colleagues, do you generally get along well with everyone?

53. Reflecting on your current job, what stands out as your favorite aspect or responsibility?

54. On the flip side, what tends to be the most irksome aspect of your job?

55. Looking back on your career, what achievement stands out as the highlight you are most proud of?

56. What kind of role do you envision taking on after your current position?

57. Would you describe yourself as someone who works to live or lives to work?

58. Does your job bring you a sense of happiness and fulfillment? If so, what aspects contribute to this, and if not, what factors play a role?

59. How do you think your 10-year-old self would react to your current profession?

60. When reflecting on your initial job experience, what stands out as the most memorable aspect?

61. At what age did you enter the workforce?

62. Could you share your experience with the least favorable job you’ve had?

63. What sparked your initial interest in your present field of work?

64. Have you ever engaged in a side hustle, or is it something you’ve contemplated?

65. Looking back, what would you consider the best career decision you’ve made?

66. Conversely, can you recall a decision in your career that you view as less than favorable?

67. How would you rate your networking skills? Do you consider yourself proficient in this area?

68. If allowed to advise your younger self on career matters, what guidance would you offer?

69. Is the concept of having a “five-year plan” something you believe in or adhere to?

70. How will you recognize that you’ve achieved your definition of success?

71. Are you eagerly anticipating retirement, or do you envision working for as long as you can?

72. Have you ever experienced imposter syndrome during your career?

73. When considering a supervisor, what characteristics do you value the most?

74. Do you currently have a mentor in your professional life, and if not, is it something you aspire to have?

75. What aspects of your career inspire and energize you the most?

76. Do after-work happy hours appeal to you as a way to unwind and socialize with colleagues?

77. What strategies do you use to stay motivated in your career?

78. Upon starting your current job, what aspect surprised you the most?

79. How do you rebound after making a mistake at work?

80. How do you manage and cope with work-related stress?

81. What specific professional goal do you hope to achieve in the next year?

82. Who has played the most significant role in influencing your career choice?

83. How does your family view your chosen career?

84. If given the chance to start over, would you pursue the same career path? Why or why not?

85. Is your work routine consistent, or does it vary from day to day or week to week?

86. What is your typical work attire?

87. Have you ever had to relocate for work purposes?

88. Would you consider relocating for work if the opportunity arose?

89. Have you experienced any memorable business trips?

90. How do you navigate and overcome setbacks in your career?

91. What amount of time do you typically spend with your family?

92. Among your family members, who do you enjoy spending time with the most, and why?

93. Which family member is the best cook?

94. How has your perception of your family evolved over the years?

95. If you are close to your family, what challenges do you face when spending time away from them?

96. Are you content with the size of your family, or do you wish it were larger?

97. Which family member has had the most profound impact on you?

98. Share your favorite story about your grandparents.

99. How would you describe your relationship with your family while growing up?

100. Among your family members, who provides you with the strongest sense of safety?


Building a meaningful connection involves actively engaging with the information he shares. Rather than just acknowledging what he says, take the opportunity to delve deeper into the conversation. Listen attentively to his words, and respond thoughtfully with a question that prompts him to elaborate on his thoughts or experiences. 

This not only demonstrates genuine interest but also encourages a more profound and meaningful exchange, fostering a deeper connection between you and him.