Best Deep Questions to Ask a Guy

This list of questions includes topics that may be deeper than you want to go with a guy, but there are also other questions that will be easy for you to tackle with him, no matter how well you already know each other. Choose your questions wisely so that you don’t make him uncomfortable or want to end the conversation.

These questions are definitely not specific to one gender, so you can also use the list of questions at the “Best Deep Questions to Ask a Girl” post here at EndangeredEmoji.com if you want to ask him more questions. Whatever your level of knowledge is about the guy you are giving these questions to, using this list will definitely deepen your knowledge and take your relationship with him to a deeper level of understanding.

Best Deep Questions to Ask a Guy

1. At what age do you think people should start settling down?

2. Is there anything you have or haven’t done that you deeply regret?

3. Would you rather be the president or a famous MMA fighter?

4. Have you ever stayed up all night to see the sunrise?

5. What scarred you the most from middle school?

6. Do you believe in fate, or do you think that things always happen because of our conscious decisions?

7. What do you feel is your greatest accomplishment at this stage of your life?

8. What was your most memorable birthday?

9. What period of history would you completely change if you had the power?

10. What was your first pet, and what age did you get it?

11. What does your perfect day look like?

12. Are you more afraid of failure or success?

13. What would you do for the people you love?

14. Who is someone you would lay down your life for?

15. If you found out you had terminal cancer, what would you do to make the most of the time you have left?

16. When was the last time you told someone you loved them–in a non-joking way?

17. What’s the last thing you crossed off your bucket list?

18. What film, book, play, or song has had a significant impact on shaping who you are?

19. What would you consider to be your greatest talent?

20. Do you think people are inherently evil or inherently good?

21. What’s something that, if you had it, you think your life would be perfect?

22. What constitutes an accomplished life?

23. What is the most worthwhile goal a person can dedicate their life to?

24. Would you say you are in touch with your emotions?

25. If a machine could exactly duplicate your mind, personality, and tendencies, would it be you? What makes you, you?