75 Best Random Questions To Ask A Guy - Make A Connection

Why is it important to know the right random questions to ask a guy?

Because there's nothing as dreadful as a boring conversation. Everyone has something interesting to say if you ask the right questions, and there is no limit when it comes to questions to ask a guy; they can funny, personal, flirty or deep depending on your relationship.

Whether you're wondering how to start a conversation with a guy or how to connect with a guy you like, you can never go wrong with our list of random questions. They are spontaneous and playful, and therefore spark interesting and unexpected conversations.

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13 Best Random Questions To Ask A Guy

You only have once chance to make a good first impression. Some random questions will lead to a great story, some will have a surprising answer, and others may even bring up embarrassing moments from the past. Either way, these best random questions will keep the conversation alive.

Here are the 13 best random questions to ask a guy:

1. If you were in a witness protection program, what would be your new name and where would you go?

How vivid is his imagination?

2. Could you survive in the wilderness for a month?

Let his inner boy scout come out to play and marvel at his excellent (or lack of) survival skills.

3. Do you ever doubt the existence of others than you?

We all feel like we're in a dream sometimes, and it's okay.

4. If you could rename the street you lived on, what would you rename it?

Changing something's name also changes the way people think of it.

5. What is the strangest thing you’ve ever eaten?

Snails, snakes, and crocodiles don't count.

6. What is one thing you refuse to share?

Everyone has boundaries, keep that in mind when thinking of what are some random questions to ask to get to know someone.

7. What’s the funniest or most amazing cell phone cover you have seen?

There are some shockingly hilarious cell phone covers out there.

8. Who around you has the worst luck?

That one person you can't take anywhere because something bad always happens when they're around.

9. What villain do you really feel for?

Ever find yourself rooting for the bad guy? You're not alone.

10. What is on your bedside table?

Maybe he has a good book you can borrow.

11. What did you think you were good at but are actually quite bad at?

We can't be good at everything, and there's nothing wrong with that.

12. What are two things you would do if you woke up to find yourself completely invisible?

This one's a thinker.

13. What are your major goals in life?

You can never go wrong with this one.

13 Random Questions To Ask A Guy To Get To Know Him

Getting to know a guy (or anyone for that matter) is all about having the right conversations with them. When considering random questions to ask a guy to get to know him, you want to go for questions that are genuinely curious and not too pushy or accusatory. We've got you covered.

Here are 13 random questions to ask a guy to get to know him:

14. What’s the one thing you would like to change about yourself?

Self-awareness is important, find out if he has mastered this rare skill.

15. In the evening, would you rather play a game, visit a relative, watch a movie, or read?

What's his idea of unwinding after a long day at work?

16. What was the best phase in your life?

We all have those moments in our past that we like to revisit now and again.

17. Would you ever take back someone who cheated?

Between love, trust, and commitment, which matters most to him?

18. Is there anything you wished would come back into fashion?

Appearances may or may not matter to him, but fashion expresses who we are and sometimes how we feel inside.

19. What kind of parent do you think you will be?

A good question to find out what values matter most to him when it comes to raising children.

20. If you were the ruler of your own country what would be the first law you would introduce?

A lot is wrong with the world we live in. If given a clean slate, how would he fix it?

21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

This will give you insight into his personality, and it's a plus if you plan to take things to the next level.

22. Who is the most intelligent person you know?

Find out about his heroes and the people he looks up to.

23. Do you judge a book by its cover?

This question is not as simple as it seems. Give him a chance to explain.

24. Does your job make you happy?

Difficulties in one's job can often spill over and affect their personal relationships.

25. If you could join any past or current music group which would you want to join?

Someone's taste in music defines who they are. You might even find out that he is currently part of a garage band.

26. Where is your favorite place in the entire world to go?

What is it about that place that makes it appealing to him?

9 Random Questions To Ask A Guy You Like

Before getting serious with a guy, you should get to know him more. These random questions to ask a guy you like are guaranteed to get him talking.

Here are 9 random questions to ask a guy you like:

27. Are you big on commitments?

If you like him, you have to know.

28. Before making a phone call, do you ever rehearse what you’re going to say? Why?

Phone call anxiety is a real thing, but maybe he can make an exception for you.

29. Do you get stressed by deadlines?

Is he a last-minute kind of person or does he like to plan ahead?

30. How do you feel about your relationship with your mother?

The nature of a guy's relationship with his mother can reveal a lot about his personality and how he treats women.

31. Are you a fan of ultimatums?

Sometimes, you owe it to yourself to be clear about your boundaries and the consequences of crossing them. Does he feel the same way?

32. What, if anything, is too serious to be joked about?

Humor is a coping mechanism that we all need, but find out where he draws the line so you don't cross any boundaries.

33. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

A good question to uncover his deepest desires.

34. What is the reason for the last time you cried?

Tears are not a sign of weakness. Find out if the guy you like is in touch with his emotions.

35. What roles do love and affection play in your life?

And can he have one without the other?

36. What is the one thing that will end a relationship for you?

And what does it take to keep a relationship with him going?

8 Random Fun Questions To Ask A Guy

Conversations don't always have to be serious. When thinking of what are random questions to ask, make sure to consider fun questions to ask a guy that can lighten the mood and make him open up. Sometimes, it's okay to keep it casual.

Here are 8 random fun questions to ask a guy:

37. What's the farthest-away place you've been?

Did the place make him feel lost or free?

38. What is your idea of fun?

Maybe he prefers having fun alone or in a group; fun wears many faces, so keep an open mind when asking this one.

39. What time do you get up?

A better way to ask if he is a morning person.

40. Do you sing in the shower?

Or does he put on a full hour-long show?

41. How Do You Know When You’ve Fallen for Someone?

It's not as simple as flipping a switch, but if you know, you know.

42. If Someone You Liked Didn’t like You Back, What Would You Do?

Rejection is inevitable, how well can he handle it?

43. Are you afraid of heights?

When thinking of what are some random questions to ask, include those that talk about fear, too.

44. Is the glass half empty or half full?

The world needs more people that focus on opportunities, not problems.

8 Random Funny Questions To Ask A Guy

A shared sense of humor can strengthen relationships. With these funny questions to ask a guy, you can laugh and be silly together.

Here are 8 random funny questions to ask a guy:

45. What are you embarrassed to admit you're afraid of?

Maybe you even share some of the same embarrassing fears.

46. What did you hate sharing as a kid?

Siblings have been known to fight each other over food, so...

47. What is your go-to karaoke song?

Ask him to sing it for you.

48. What’s the sexiest animal on the planet?

Sexiness is in the eye of the beholder.

49. What’s the stupidest thing you ever did at work?

Was it an accident or did he do it on purpose? And would he do it again?

50. Are you allergic to lipstick?

He might have to wear the lipstick first, or at least eat it.

51. If you had to live without your phone for a week, what would you miss about it the most?

That is if he can even survive the week.

52. Would you rather speak all languages or speak to animals?

Animals always seem to ignore people when they talk; it would be fun to get inside their brains.

9 Random Interesting Questions To Ask A Guy

The secret to having great conversations is asking the right questions. Interesting questions to ask a guy can reveal the most unexpected things about him.

Here are 9 random interesting questions to ask a guy:

53. Do You Prefer Casual Dating or Long-Term Relationships?

This question always reveals the guy who knows what he wants from a relationship.

54. What is always in your fridge?

Is he all about healthy living or quick and easy meals?

55. Do you consider yourself a feminist?

Don't let him trick you. ost people say they are feminists even though they don't understand the meaning of the word.

56. Do you believe in past lives?

What about reincarnation?

57. Have You Ever Experienced Unrequited Love?

Its the worst but still, better to have loved and lost.

58. How polite do you consider yourself?

Hopefully, he's not too polite for his own good.

59. How often do you read?

The brain is a muscle and it needs exercising to stay sharp.

60. What do you prefer – spontaneity or stability?

Remember, it's not all black and white- you can have both stability and spontaneity.

61. What is the first thing you notice about a woman?

For most guys, its the smile.

13 Random But Deep Questions To Ask A Guy

Deep questions tend to be too serious at times. But if you really want to get to know someone on a personal level, then you have to ask the deepest questions. Our list of random deep questions to ask a guy can help you create stronger bonds.

Here are 13 random but deep questions to ask a guy:

62. What is the one rule you have for yourself that you will never break?

And what's the story behind this rule?

63. Do You Idealize Your Parent’s Relationship?

As we grow up, it can be heartbreaking to find out that our parents are just as normal and confused about life as we are, but we still look up to them.

64. Do You Idealize Your Parent’s Relationship?

As we grow up, it can be heartbreaking to find out that our parents are just as normal and confused about life as we are, but we still look up to them.

65. Are you afraid of growing old?

They say we should age gracefully, but can he really give up youth that easily?

66. What frightens you most when it comes to love?

The dilemma of love is that the more you have, the more you have to lose.

67. What is your opinion of equal pay?

Should men and women be treated as equals both in the workplace and in their households?

68. Do you think destiny is real?

This one roughly translates to: do you think we have free will?

69. Are we “born” to meet our “other half”?

Did the fairy tales lie, or is Prince Charming somewhere on the other side of the world waiting for us?

70. Do you think it will ever be necessary to take the law into your own hands?

Forget all the movies you've watched where vigilantes save the day. In real life, things are just a bit more complicated.

71. If you have been diagnosed with depression, would you be ashamed of it?

Depression is nothing to be ashamed of, but it can take a toll if not treated.

72. What human trait is useful now but would have been disadvantageous in the past?

We may have evolved into more intelligent beings, but could modern human beings survive in an uncivilized world?

73. What’s the most important value you would teach a young person?

There are so many things children need to learn, but he only has to pick one.

74. What’s the one thing that should be taught, but isn’t?

Schools tend to teach technical things and not nearly enough life skills to help students survive in the real world.

75. Do you believe that robots will make humans obsolete?

In a future where machines do all the work, what will humans do?

How To Pick The Best Random Questions To Ask A Guy

Having random questions to ask someone handy can help you whether you're getting to know a guy, or you are simply looking to have an interesting conversation. However, not all guys are the same, so pick your questions carefully.

Here is how to pick the best random questions to ask a guy:

1. Consider Your Relationship

The nature of your relationships determines the type of questions you can ask a guy. Some questions are more personal than others, so it all depends on who the guy is. A personal question may not be appropriate when getting to know a coworker, but it may work on a first date. So, when thinking of what are random questions to ask, consider the stage you are in. Always.

2. Don't Be Pushy

If you happen to ask a question that a guy is not comfortable answering, don't push it. Take the loss and move on before it becomes awkward.

3. Ask Follow Up Questions

A conversation is not all about asking and answering random questions. These questions to ask a guy as only here to act as a guide. Listen to the guy you're talking to and allow the conversation to flow naturally.

Downloadable and Printable List of Random Questions To Ask A Guy

Here is a downloadable and printable List of Random Questions To Ask A Guy (right click the image and select Save Image As...):

More Great Ways To Talk to Guys

When you like a guy, it's normal to be a little nervous around him. If this happens, don't worry. We have more awesome tips and questions that can help you get through your next hundred conversations.

Here are more great ways to talk to guys:

1. To have funny, deep, and interesting conversations, you first need to learn how to ask a guy out. Our guide on how to get a boy to like you gives precise and helpful tips when you want to initiate a relationship with a guy you like.
2. Maybe you have already pictured your life together, but you're afraid to make the first move. Knowing how to flirt with a guy can help you overcome your fear of rejection and get what you want.
3.  Dating can be a little awkward, especially in the beginning. You don't want to move too fast and scare him away, so before hitting send, ask yourself this question, 'should I text him?

In Conclusion

There you have it; a dependable list of random questions to ask a guy. Once you figure out how to start a conversation with a guy, all you have to do is pick the right questions to ask a guy.

These questions will help your conversations along and get your crush, your guy friend, or even your boyfriend to open up some more.

You may get unexpected answers, but its all part of the process. And we'll be here to help you on how to tell if a guy likes you or if he's worth your time and effort.