Best Random Questions to Ask a Guy

Here is a great list of random questions to ask a guy you are with. This list should come in handy for any occasion, but especially if you are having a hard time figuring him out. Keep asking these questions, along with follow-up questions, until you strike gold with a topic he enjoys talking about. Then, you’ll be off and running!

You can have some random fun with this list of questions and a guy whose game for going along with unexpected questions coming from you. Jump around in this list to whatever questions you find the most entertaining and random, and you are sure to have a randomly good time with your guy friend(s).

Best Random Questions to Ask a Guy

1. What actor will you always associate with a particular character?

2. What would your nickname be in a witness protection program?

3. Have you ever been banned from a public place?

4. What would the first colony on another planet need to survive?

5. What’s the best mode of transportation?

6. If you won $100 million, what would you buy first?

7. What villain do you really feel for?

8. What conspiracy theory do you actually believe in?

9. What’s the weirdest habit you have?

10. Who is your role model?

11. What’s a song you know all the lyrics to?

12. If you gave up all your technology for a week, do you think your life would be better or worse?

13. What would be the funniest thing to fill a pinata with?

14. If there were such a thing as the internet Olympics, what sports would be in it?

15. What seems delicious but actually tastes terrible?

16. What’s your favorite joke?

17. If you had to replace your hands with everyday household objects, what would they be?

18. What’s the coolest thing you’ve ever done by yourself?

19. What’s something you’ve done that you would not recommend anyone else do?

20. Chicken or beef?

21. Do you think the Avengers or the Justice League would win?

22. Do you think paper books will die out?

23. Have you ever gotten really drunk and done something you regret?

24. Do you think guys and girls can really have just-friendships?

25. Do you have a favorite documentary?

26. What good things did Hitler do?

27. Do you like crosswords?

28. What are the disadvantages of shopping online?

29. What word do you hate the sound of?

30. Florida or California?

31. One Direction or Justin Bieber?

32. What’s the tastiest fish you ever tried?

33. Are you hungry?

34. What is something that reminds you of the sun?

35. Would you rather live in the countryside or the city?

36. Is dying healthy?

37. Is there an app that needs to be made?

38. What is the last thing you searched on the internet?

39. If you had to live on a desert island for a month, what would you absolutely need?

40. Is there a reality tv show you would want to be on?

41. What is the last thing you do before you go to bed most nights, if not every night?

42. Which foot do you put your socks on first? 

43. What is your ideal temperature? 

44. What is one sound that really bothers you?

45. Would you rather swim in the ocean or a pool?

46. What was your favorite subject in school?

47. Do you have a favorite day of the week?

48. What makes a girl instantly attractive to you?

49. What do you make sure you always have in your refrigerator?

50. What household chores do you like doing the most?