51 Random Questions To Ask A Guy: Deep And Engaging!

random questions to ask a guy

51 Random Questions To Ask A Guy To Know Him Better

The other day, we were having a conversation about relationships and how people go from being lovers to completely being indifferent for some reasons and that sparked another conversation about random questions to ask a guy when you are dating or just plain interested in him.

Asking random questions is a great way to break the “ice in a conversation” and to get to know people generally, so it is a great idea to ask people questions if you want to get to know them a little better.

I ask questions a lot. Even seemingly “stupid” ones but I have found that no matter how think a question is (questions shouldn’t be inappropriate of course), go ahead and ask as long as it is not mockery, out of place and you just might be surprised at what you learn at the end of the day!

The Value Of Asking Questions

One thing I have noticed is that people especially men do not like being “questioned” but communication is the “oil that practically “drives” healthy relationships so asking questions is healthy.

Striking a balance is very important.

There are uncomfortable questions people avoid asking in many relationships that has led to the irrevocable breakdown of relationships but this can be avoided during the dating phase of a relationship.

Asking questions shouldn’t be about being antagonistic. It should be done with respect and care.

According to an article published by National Library of Medicine, “The purpose and practice of active questioning has its roots in ancient philosophic traditions. Socrates is well known for using questioning to probe the validity of an assumption, analyze the logic of an argument, and explore the unknown“.

These random questions to ask a guy will clear any assumptions and preconceived notions you may have about him, explore the unknown and get to know him better.

Related: The Four Most Uncomfortable Questions Avoided In Relationships

Random Questions To Ask A Guy: Deep

Now that we have established that asking questions is actually very healthy for relationship growth and a great way to get to know people better, let us have a look at the random questions to ask a guy if you want to understand him better and perhaps get answers to some of the questions you have been dying to ask him.

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random questions to ask a guy
Random Questions To Ask A Guy

1. Where did you grow up?

2. Who is the one person you would say has impacted your life most positively?

3. What is one thing you regret?

4. What are your thoughts about gender equality?

5. Do you believe that Climate Change is real?

6. Which of your parents are you close to?

7. Have you ever believed in a conspiracy theory and then found out it was all a lie?

8. Who is your mentor? Professionally and personally?

9. How did you feel when you achieved a goal you set for yourself this year?

10. What is that one thing you wish you have?

11. Do you believe in the idea of a God looking down on us from the heavens?

12. What are your thoughts about religion generally?

13. What do you think about the War in Ukraine?

14. How would you like to make the world a little better?

15. What and whom has shaped your thought processes mostly?


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Random Questions To Ask A Guy Flirty

Girl, you are interested in this guy so it is absolutely fine to ask him some flirty questions too!

Here are some random questions to ask a guy if you want to be flirty and naughty!

16. What are some of your sexual fantasies?

17. What would you do if I were to kiss you right now?

18. How did your first kiss feel like?

19. Would you rather stay home for a cozy dinner date or go out?

20. What is your ideal of a healthy relationship?

21. Do you like public display of affection (PDA)?

22. Are you a hugger?

23. Who was your high school crush?

24. Would you rather shower together with your partner or shower alone?

25. What pet name would you like to me call you if I were to give you one?

26. How would feel like when you are spanked during love making?

27. Do you get erotic dreams? Tell me about them

28. Would you like frolicking naked on a beach?

29. What is your innermost desire when it comes to sex?

30. What part of your body turns you on the most?

random questions to ask a guy
Random Questions To Ask A Guy

Random Questions To Ask A Guy Funny

Now, it is time to get in some laughs after the deep and steamy questions you have been asking.

Let’s make him laugh with these funny random questions. That way, you end up relaxed and comfortable around each other.

Here are some funny random questions to ask a guy that you fancy.

31. What is one of your most embarrassing moments?

32. Which of your siblings you absolutely adore but exasperates you in a hilarious way?

33. Have you ever farted in the presence of a girlfriend?

34. Tell me about the one thing you do in secret that is absolutely hilarious

35. How do you keep a straight face when something makes you want to laugh but it is inappropriate?

36. Have you ever farted in a crowded space?

37. What do you think is the most stupid thing you have ever done?

38. Tell me the story behind the funniest nickname you’ve ever had

39. What is your most funniest memory from your childhood?

40. Has anyone ever walked in on you naked?

41. What is your most embarrassing moment at work that had you in snitches after?

42. How did you handle your first awkward “groping”?

43. What cartoon character makes you laugh the most?

44. What is the cheesiest pick up line you ever used?

45. Have you ever worn a girlfriend’s undies?

46. Have you talked to yourself when you are alone?

47. Has anyone ever called you a fool for being a fool?

48. Have you ever made a prank call?

49. What is the most dumbest idea you’ve ever had?

50. Would you rather be a zombie or a vampire?

51. Tell me about the most awkward situation you have ever been in.

Related: 21 Flirty Questions To Ask The Guy That You Like

random questions to ask a guy
Random Questions To Ask A Guy

Conclusion on Random Questions To Ask A Guy

Asking questions is a great way to start conversations. Questions are typical ice breakers and these random questions to ask a guy are definitely going to help you start great conversations and get to know a guy better.

Go with the flow. These random questions will lead to even more questions and answers. You will both get to know one another better because he is definitely going to ask some questions of his own!

Girl, go ahead and ask away because if you don’t ask, you won’t know!

Check out these 195 Questions That Will Build Deep Intimacy With Your Partner.

Don’t forget to share this on your social media. Tweet, Pin and Facebook! Whichever one works for you!

random questions to ask a guy
Random Questions To Ask A Guy

Kinging Queen

Jennifer Pompaski
Jennifer Pompaski

Hi, my name is Jennifer. I am an Engineer by day and a blogger 24/7. I am passionate about Self Improvement & Productivity and this blog is dedicated to that passion! I hope you find it worthwhile each time you visit! If you do find anything helpful on here, kindly share because sharing is caring!

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