121 Open Ended Questions to Ask a Guy: Get To Know Him Better

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Want to break the ice and get into captivating conversations with a date, coworker, or friend?

Say hello to our collection of open ended questions to ask a guy- the ultimate conversation starters that will unlock a world of meaningful interactions and playful banter!

If starting a convo with a guy feels a bit daunting, fear not, because these questions are here to save the day! 

In case you’re wondering about the definition of open ended questions, these are types of queries that don’t have a simple “yes” or “no” or “static” answer – they require a longer response and more detail about the topic.

Instead, they encourage the person to share their thoughts, feelings, or experiences in their own words. 

The following set of prompts is divided into different rounds of topics- whether you’re looking for friendly questions to ask a guy about random stuff or looking for open ended questions to ask your crush to know his thoughts about dating and romance.

To use these, just ask them the questions and listen carefully to their response and show genuine interest in what they say.

For more conversation starters with a guy, try our list of this or that for adults or our list of truth questions for friends

Fun Open Ended Questions to Ask a Guy

Get ready to spark some laughter and curiosity with these light-hearted and entertaining topics.

From sharing funny scenarios to quirky preferences, these good questions to ask a guy will keep the conversation fun and engaging.

1. Where do you go when you want to have a fun night out and what makes it fun?

2. Where is the weirdest place you have spent the night and how did you end up there?

3. Who do you enjoy going out to party with and why?

4. If you could celebrate your next birthday with no budget cap what would you do?

5. What is something your friends made you go to that you thought would suck but turned out to be a lot of fun?

6. If you could go anywhere on a fun vacation where would you go and why?

7. What is something that you love to have in your car that other people may find strange and why do you have it?

8. What is something you like to add to your coffee to add a little razzle-dazzle and what gives it the kick?

9. What’s the silliest childhood fear you had as a kid that you’ve got over?

10. What are examples of things you find funny that most other people do not?

11. Tell me about a time you have you considered cussing someone out for something really stupid?

12. When was the last time you laughed so hard you cried?

13. What’s your favorite dad joke or pun that never fails to make others laugh? Try me, ha ha!

If you want another list of good open ended questions, check this guide.

Man relaxed in chair on laptop. D

Random Open Ended Questions to Ask a Guy

Get ready for a round of spontaneity and surprise! 

These random questions to ask a guy will cover a wide range of topics, ensuring you never run out of things to talk about, whether you’re on a date, texting, or hanging out at a party.

14. Were you the funny kid, smart kid, sports kid and how did others treat you playing that role?

15. What was your favorite subject in school and did it impact on your career path?

16. What is something you are doing as an adult that you wish you could have done as a child?

17. Do you have any random talents or party tricks that alway impress?

18. What is your favorite board game and when is the last time you played it?

19. Tell me about your morning routine?

20. What is your go-to feel-good meal and what makes it a comfort food?

21. If you could only eat one sugary treat for the rest of your life what would it be and why?

22. How often do you need to clip your toenails and do you do it religiously?

23. Do you need time in the morning to wake up, or are you ready to go as soon as your feet hit the floor?

24. What’s your current favorite meme or online trend?

25. What is your favorite social media platform, and why?

26. If you could time travel, which event would you go back witness and why?

27. What’s the most adventurous thing you’ve done, would you do it again?

28. What’s your go-to karaoke song, and would you be to sing it for me?

29. Where do you draw inspiration when it comes to decorating your home?

30. What is a household chore you hate doing the most and why?

31. What are you expected to do as an adult but can’t be bothered?

Two happy bikers eating canned foods while sitting.

Open Ended Questions to Ask a Guy About Dating

Dive into the world of romance with these date questions to ask a guy that will uncover his thoughts on dating and relationships.

From his preferences to dream date destinations, you’ll get the chance to discover what makes their heart flutter.

32. What is a red flag in a partner?

33. What is a green flag in a partner?

34. What is a beige flag in a partner?

35. Where do you like to go for a first date and what makes it ideal?

36. Describe the most adventurous first date you have been on?

37. What is the most romantic thing someone can do on a first date in your opinion?

38. Do you think showing your true self on the first date or only your highlight reel is important?

39. What things aren’t a good idea to do on the first few dates with someone?

40. Where do you like to go for second dates and why?

41. What is something that will guarantee you are asking for a second date?

42. Do you like to pick up your dates or meet them at the place of the date and why?

43. How long does it take you to get ready for a date and what can hold you up?

44. What is something that makes you want to end a date early?

45. What is the most creative way someone has asked you out on a date?

46. What is the weirdest thing you have done or experienced on a date?

47. What is the most extreme thing you have done to impress someone on a date?

48. If you been on a date with someone, and it didn’t work out romantically, but you became good friends – what makes you work as a friends but not as a couple?

49. Describe your most awful date?

50. Describe your best date?

51. What are your thoughts on personal growth and self-improvement through dating?

52. Do you like to get to know someone through texting or wait for an in-person meeting to get to know them more and why?

53. What is a cheesy pickup line you have used, and what made it work?

54. What open ended questions do you pull out on a date and why do they work?

55. What is your biggest dealbreaker and why?

56. Describe what someone could do that would make you ghost them?

57. What is something subtle that someone can do to catch your attention and what makes that get you?

Wondering what to ask a guy on a date? Try our date night questions, funny questions to ask on a first date, and second date questions.

Smiling interracial couple holding a cup in front of a bonfire.

Open Ended Questions to Ask a Guy About Work

Discover the ambitions and passions of the guy you’re talking to with these career-oriented questions to ask him.

Each topic will provide insights into their professional aspirations and goals.

58. Tell me about your dream job.

59. What did you dream about being as a child when you grew up and how close it that to your current life?

60. If money wasn’t an issue, what would you do for a living and why?

61. Is this the job you plan on working at until you retire, or do you plan on moving on to something else eventually?

62. At what age do you want to retire and what will you do with your life after that?

63. What kind of side hustles have you considered doing and why?

64. What inspired you to pursue your current career path or job

65. How did you get the job you are at now?

66. Describe a typical day at work?

67. What is something you would like your workplace to have that would make your day go smoother and why?

68. How do you approach a coworker who is not doing their job to tell them?

69. What does your workplace do to show their staff they are appreciated?

70. If you had a problem with your boss, how would you approach them?

71. How did your workplace handle the pandemic?

72. What are your favorites parts of your job?

73. What perks do you get from your job?

74. How often do you go on vacation and do you have to tap into work when you are away?

75. How do you maintain a work-life balance?

76. What activities help you take off a load after work?

77. What is the worst way you have quit a job?

78. What reasons have you have been fired from a job?

79. What is something you wish to go back to school for?

African American man sitting on a chair and working on his laptop beside a french bulldog.

Open Ended Questions to Ask a Guy About Hobbies

Everyone has hobbies and it just makes life so much better.

From sports and favorite pastimes, this round of interesting questions to ask a guy will uncover his passions and interests beyond the surface.

80. How do you like to spend your free time?

81. Tell me about the hobbies you had as a child.

82. Tell me about your current hobbies.

83. What is something you wish you could afford to do as a hobby and why?

84. What is the weirdest hobby you have had and what makes it weird?

85. What is the strangest hobby you have ever heard of and what makes it strange?

86. Where do you get inspiration to try something new from?

87. Once you have mastered something, do you lose interest or continue to do it and why?

88. What new skills and challenges have your hobbies taught you?

89. Have you ever shared your hobbies with friends or family, and how did they react?

90. If you could make a living doing something you enjoy, what would it be?

91. What is a hobby that one of your friends has that you think is stupid and why?

92. What is a hobby that you do not recommend and why?

93. What hobby do you think sounds really dull? What puts you off?

94. What is a popular hobby in the area where you live that people who don’t live there probably have never heard of and what makes it popular?

95. Tell me about something that you collect?

96. Tell me about a sport that you enjoy watching or playing.

97. Have you ever played any sports competitively or on a team? If so, what was it like?

98. Do you have any sports goals or achievements for the future?

99. Are there any sports events or tournaments you’d like to attend in person soon and what is attractive about them?

100. What is a hobby that you hope your future children will like and why?

Friends playing beach tennis game.

Personal Open Ended Questions to Ask a Guy

Go beyond the small talk and create a deeper connection with these deep and personal questions to ask a guy.

Whether you’re on a date or just getting to know each other, this round will lead to heartfelt and memorable conversations that leave a lasting impression.

101. Who do you go to first when you have good news and why?

102. Have you ever opened up to someone and regretted telling them anything?

103. What characteristics make a good advice giver?

104. What is the best piece of advice you have ever been given?

105. What is the worst piece of advice you have given to someone?

106. Can you tell me about a time that you were terrified?

107. What do you do when feeling down and needing to cheer yourself up?

108. When your life is feeling overwhelming, what is something you do to feel more grounded?

109. How often do you take the time to focus on self-care and what do you do?

110. What is something that always makes you feel good about yourself?

111. Tell me about something you have accomplished that you are really proud of?

112. What big challenges have you faced that you thought you might never overcome?

113. What has been your biggest lesson in life this far?

114. How long did it take for you to learn that lesson and what stopped you from doing it faster?

115. What would you say if you could warn your younger self of a situation or person?

116. What could a friend do that would make you not want to be friends with them anymore?

117. What do you plan on doing differently to raise your kids than what your parents did?

118. When was the last time you spent the evening staring at the stars and how did it make you feel?

119. When you reflect on your life, are you proud of yourself, full of regret, or a mixture of the two?

120. What do you think happens when we die?

121. What is something that you hope to achieve before you die and why?

Man stretching and yawning on laptop.

Final Thoughts

We hope you enjoyed this list of great questions to ask a guy and had fun exploring engaging conversations with him!

Share your thoughts and experiences in the comments below – we’d love to hear how these questions made your interactions more meaningful and enjoyable!

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