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50 Random and Funny Questions to Ask a Guy

What are you supposed to ask a guy to get to know them? Find all the random and funny questions you should be asking here.

Random QuestionsHow do you get to know a guy? No you don’t hire a private investigator, that’s just creepy!!

You just ask them, men might be secretive creatures (tell me about it!) but with the right questions they can be known to spill their hearts out!

Getting to know a guy can be as difficult as trying to solve the world’ hunger issue; it’s tricky, unsolvable, and a girl has no idea where to start from! (Do NOT forget to read our previous post where we talked about the top conversation starters to chat up the guy you like)

For that reason we’ve compiled a not-so-modest list of no less than 50 questions that you could ask a guy, to get started unraveling their mystery. (Many are on the funny side!)

Be prepared to laugh, get angry, be shocked and fall in love. The way to a guy’s heart is through his mind (and his stomach so ask him these questions while you cook him a delicious meal), so start digging in!

1.  Would you keep it If I told you a secret?

He is answer is rather predictable here, but what you’re after is the eagerness of keeping your secret. If he is truly interested he will even push you to share that secret! (So you better have one to spare!)

2. You’re in a woman’s body for a day. What would you long to learn first?

- This is the ideal question for getting to know what he cannot understand about women, what he finds strange or nonsensical, what he admires or loves about women! Careful with this one – it can take a curvy turn down perverse street real quick!

3. Do you feel there’s actually a difference between loving and falling in love for someone?

Even if he doesn’t believe there’s any difference, if he actually tries to elaborately explain his grounds for saying so, this shows true interest in you.

Men tend to not distinguish between the two and they know how most women do distinguish between loving and falling in love. And this question will probably tell you how much he has fallen himself! [Read - 22 Obvious Signs a Guy Loves You]

4. Where would you rather be right now?

This one unlocks his present fantasies, what intrigues and excites him! What if you are part of them?! Hopefully he answers – “nowhere, right here with you!” Wouldn’t that be the perfect answer!

5. If there were one person whom you would want to bring back from the dead, who would it be?

Famous or not, his answer will show you who he misses and finds admirable in life. And you can tell a lot by looking at someone’s role model.

6. A supermarket cashier is being rude, how do you handle it?

This is an opportunity to know how much he values respect and others’ dignity. Will he talk back or take the high road? For how long can he keep his cool before getting angry and other temper-related issues will be answered through this simple question!

7. What was your first thought about me when you saw me?

Don’t go for this one unless you’re brave enough. First impressions aren’t always the most flattering ones. Go for it and learn how you come across when guys first meet you!

8. Do you ever think about your first love?

Alright, so here you’re getting into darker alleys of his heart. The thing is when guys love, they do it passionately, so don’t be surprised if he starts pouring his heart out.

9. What’s the hardest thing you’ve ever done?

Here you’re giving him a chance to indirectly brag about himself, which is a good thing, men love being looked upon.

10. You’re turning into a city, what would that be?

A lovely way to get to know his aspirations, how he regards himself and what he believes in.

11. You got a time machine and you’re traveling back to your childhood, what you would say to the younger version of you?

An amazing question to ask your date or your for years boyfriend; his answer will illustrate his regrets, what he has learnt in life, what he regards to be his weak aspect.

12. What you consider to be the most awesome job in this world?

If he answers his, he’s rather accomplished. Even if he answers something crazy or funny, you get to know what he counts as pleasurable.

13. Favorite cartoon, comic or super-hero when you were young?

A witty question to delve into his childhood, to learn his fears, his dreams and what he identified with. Was he a Batman, or was he a Snoopy? The answer might just surprise you when he says “Marmaduke!”

14. Is there anything about you that you don’t like, or would like to change?

Know that he might wish to avoid this question. So don’t pressure. His answer will reveal his insecurities and his strong points and guys don’t like to make those public knowledge.

15. What you would take with you during a Zombie Apocalypse?

Not necessarily a fun question; his answer will give you insight to how thoughtful and prepared he is for the future (even if we talk about a fictional, so-no-happening scenario!)

16.Who would you kill to put them out of their misery during the same Zombie Apocalypse?

A twisted way of asking who matters the most to him. Will it be his mum, or his best buddy?

17. What’s the one super-hero power everyone should be entitled to?

Another way of seeing what he regards as weakness or what his insecurities might be.

18. What your dream girl looks like?

A question to probe into his romantic world, the values and aspects of human nature that he thinks to be important. Is he going to just talk about appearance?

19. You get to dine with famous people, who would you invite?

This is a great question to get to know who he admires, or who he loathes enough to bring to a table with other equally awkward people!

20. The most ridiculous memory from your school years?

Prepare to hear something utterly weird, hilarious, or just plain disgusting. You asked for it!

21. What’s the funniest sex incident that ever happened to you?

You will get to learn what he is into, what turns him off, and whether he has a sense of humor as to laugh about it!

We love questions; they lead us down unforeseen pathways and into the craziest and funniest roads. Especially when your questions are insane or just plain absurd, the fun gets bigger!

Below are few more random, plus funny questions which you could ask a guy- so that you never run out of things to say!

22. What is your dream car?

23. What kind of movies do you like?

24. When was the last time you cried?

24. Do you like horror movies? Can you watch one alone in a dark room?

25. What is your favorite pass time?

26. Are you an adventure lover?

27. How often do you take a bath?

28. How often do you change your underwear and socks?

29. Who is your favorite actor?

30. You just won a million dollars, what’s your first purchase?

31. Who is your role model?

32. What is your favorite food? Do you like spicy food?

33. Are you a cook, or just an eater?

33. What your will prefer – Getting together party with your friends or a romantic dinner with your wife/girlfriend?(A really tricky question and you won’t get the right answer 99% of the time)

34. Are you a living-together or let’s-get-married person? (Careful, you might scare him off with this one!)

35. Would you get married through an arranged marriage?

36. Do you have any pets?

37.  Cat or dog person, why?

38. 40 miles/hour or 60 miles/hour – Which one is better (You don’t need an answer for this actually because 99% of the time it will be 60 miles/hour or possibly more)

39. “Consumption of alcoholic beverages impairs your ability to drive a car or operate machinery, and may cause health problems” – What is your opinion on this?

40. Friends with benefits, ever had one? Do you approve of it?

41. Have you ever stolen money from your Dad’s wallet?

42. What is your favorite color, why do you think that is?

43. What do you do when you are all alone?

44. What’s your dream job, ever tried to make it happen?

45. What kind of music do you like?

46. What was the biggest mistake of your life?

47. What has been your “Best Day” so far and why?

48. Have you ever been broken-hearted? What happened?

49. Do you trust people easily or is it hard for you?

50. What do you think are your strong points?

These questions are not meant to be interview-style. Memorize a few and use them when silences creep in, or when it feels appropriate to. Think of them as props to help you get to know each other!

Surely, you must have some other questions on your mind? Care to share your ideas with everybody else? Just post them below :-)


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