random questions to ask a guy - main in postPeople like a dash of the unexpected, and knowing some random questions to ask a guy will have you building rapport with other men wherever you go.

When it comes to your likeability, a little randomness can go a long way.

Knowing a handful of the right questions to ask can improve your relationships with coworkers, help you make friends out of acquaintances, and give you something to talk about when meeting friends of friends. Use this list of questions to ask a guy the next time you need to make a good first impression or hope to get closer to someone you already know.

With a few great random questions in your back pocket you can walk into any situation with confidence.

I recommend reading through all of these 43 random questions to ask a guy to find your absolute favorites… but if you’re looking for something specific, you can click the links below to jump to that section:

Contents

6 Best Random Questions To Ask A Guy

Talking to guys you don’t know can be nerve-wracking. You want to be yourself, but you also want to come across as likeable and interesting.

Scroll through this list to find a few questions that suit your personality and rest assured that you’ll be conversing naturally in no time.

Here are 6 of the best random questions to ask a guy:

1. If you put out a magazine, what would you name it and what would be in it?

Find out what your dude is interested in and passionate about.

random questions to ask a guy - If you put out a magazine, what would you name it and what would be in it

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

What is Tyler Durden doing in ancient Greece?

3. What is the most fun thing someone could have in their backyard?

Big boys need big toys when they play outside.

4. If you were in witness protection what would your nickname be?

Then ask how else he would reinvent himself given the chance.

random questions to ask a guy - If you were in witness protection what would your nickname be

5. Have you ever been banned from somewhere public?

This will tell you if he’s got a rebellious streak.

6. What do you want to be written on your tombstone?

A tombstone summarizes a person’s life. How would he sum his up?

6 Random Conversation Starters to Ask a Guy

Good conversations have to be able to flow naturally, which is why these conversation starters give you a place to start and possibilities for what to talk about next. 

Choose from any one of these conversation topics and forget about running out of things to talk about.

Here are 6 random conversation starters to ask a guy:

7. What would the first colony on another planet be needing?

What would we need to support ourselves on another planet?

random questions to ask a guy - What would the first colony on another planet be needing

8. What TV news story is getting more attention than it should?

Bringing up current can be risky but its a great conversation starter.

9. What is your go-to activity when you’re bored?

How he occupies his mind is a sign of the kind of person he is.

10. What do you think is the best mode of transportation?

Don’t forget to consider cost, speed, and convenience.

random questions to ask a guy - What do you think is the best mode of transportation

11. Describe the greatest, funniest adventure you have ever been on.

Getting a guy to tell a story is a great way to show interest.

12. If you won 100 million dollars, what would you buy first?

I believe the correct answer is “another round of drinks.”

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

Making friends is important for your health and your happiness, but it gets harder to do the older we get. Make the process a little easier with these questions to ask a guy to get to know him.

Of all the questions to ask a guy, get to know you questions are the best at helping you make real, lasting friendships.

Here are 6 awesome random questions to get to know him:

13. What villain do you really feel for?

The best villains are ones we can almost identify with. Who does he identify with?

random questions to ask a guy - What villain do you really feel for

14. What conspiracy theory do you actually believe?

This question starts great conversations that can be very revealing.

15. What is something most people do easily but you find very difficult?

Find out what’s challenging for him. It will tell you a lot.

16. If you could trade your identity with someone, who it would be?

Who’s the person with the fewest responsibilities?

random questions to ask a guy - If you could trade your identity with someone, who it would be

17. If someone else’s child was being annoying would you tell them off?

A dude’s attitude towards kids is very telling.

18. What’s the weirdest thing about you?

Friends are people who are the same kind of weird.

5 Random, Personal Questions To Ask A Guy

Do you ever get tired of talking about the weather or the last night’s game? Do you want to really get to know the guys you spend time around?

These personal questions to ask a guy will help you turn acquaintances to friends and help you discover what makes your friends tick.

Here are 5 powerful random, personal questions to ask a guy:

19. What are some of the morals you live by?

A man’s moral code guides his every decision. This will help you really understand your bro.

random questions to ask a guy - What are some of the morals you live by

20. Have you ever had a crush on a much older woman?

Every guy has found himself daydreaming about a teacher or a buddy’s mom.

21. Who are your role models?

Be sure to ask why he looks up to them.

22. What is the wildest thing you have ever done?

It’s the wild things that make life exciting.

random questions to ask a guy - What is the wildest thing you have ever done

23. If you could redo any past moment what would it be?

And would it be to experience it again or to do it differently?

5 Random Questions To Ask A Guy, That You Can Also Ask Girls

Hopefully all of these random questions to ask have you feeling more confident in your interactions with the fellas. You might even be thinking about gaining the same confidence when approaching girls.

Look no further than these random questions to ask a girl. These questions are so flexible that you can be sure that no matter who you’re talking to, you’re on your way to a great conversation.

Here are 5 random questions to ask a guy that you can also ask girls:

24. What are some songs you know by heart?

There’s nothing like the satisfaction of perfectly singing along to a song.

25. What behaviors make you think a person is creepy?

Creep identification is a very important skill.

random questions to ask a guy - What behaviors make you think a person is creepy

26. How would your ex describe you? Be descriptive on personality.

Our exes have seen the best and worst of us. How they think of us after it’s all over is very telling.

27. What do you think would happen if you gave up all of your technology for a month?

Society is so hooked on tech, who knows what would happen without it.

28. What activity do you do that makes you feel most like yourself?

The world would be a better place if we all spent more time doing the things that makes us feel whole.

random questions to ask a guy -What activity do you do that makes you feel most like yourself

5 Random and Funny Questions to Ask a Guy

It feels good to laugh. Not only does it feel good, turns out its really good for you.

Maybe that’s why we like funny people. With a handful of these funny questions to ask, you’ll be making the guys healthier at the same time you’re making healthier friendships.

Here are 5 random and funny questions to ask a guy:

29. What would be the funniest thing to fill a piñata with?

It turns out adult piñatas are a real thing.

30. If there were internet Olympics, what sports would be in it?

Dankest memes? Worst Clickbait? Grumpiest Cat?

31. What seems delicious but tastes terrible?

How can something called Cocoa Butter not be a delicious spread?

random questions to ask a guy - What seems delicious but tastes terrible

32. If you had to replace your hands with objects already in your house, what would you choose?

Edward Scissorhands made a questionable choice.

33. What is your favorite joke?

Give the other person a chance to make you laugh, it’ll go a long way.

5 Random, Interesting Questions to Ask a Guy

Interesting questions challenge our minds and make us smarter, more engaging people. Keep your buddies’ minds sharp with these interesting questions to ask a guy.

Here are 5 random, interesting questions to ask a guy:

34. What’s the future of dating?

Dating has changed so much in the last 100 years. Where does he see it going next?

random questions to ask a guy - Whats the future of dating

35. What is the most useful thing your mom or dad has taught you?

We pick up a lot of things from our parents, some intended and some not.

36. Name the coolest thing you’ve done by yourself.

A solo adventure is a growing experience like no other.

37. How do you show your love for others?

It’s important to understand how the people we’re close to show their affection.

random questions to ask a guy - How do you show your love for others

38. What’s your first thought when you wake up?

What motivates this guy to start each day?

5 Random, but Deep Questions to Ask a Guy

The best nights always seem to revolve around good friends tackling deep conversation topics. Don’t wait for memorable nights come around, go out and make them with some deep questions to ask.

Here are 5 random but deep questions to ask a guy:

39. What do your clothes say about you?

What image of himself does he present to the world?

40. How do you feel about your age?

Like most things in life, being content with age is challenging.

random questions to ask a guy - How do you feel about your age

41. What is one thing you have done you would not let someone else do?

We learn from our mistakes. What is one mistake he thinks isn’t worth the lesson?

42. Do you like experimenting with new things in life?

Some prefer variety, others prefer routine. How does he feel?

43. Are you happier when you’re single or in a relationship?

Finding a way to be happy no matter your circumstance is the real challenge.

random questions to ask a guy - Are you happier when youre single or in a relationship

Downloadable List of Random Questions To Ask A Guy

Here is a downloadable list of random questions to ask a guy (right click the image and select Save Image As…):

list of random questions to ask a guy

More Great Random Questions

If these random questions have piqued your interest, check out the links below for more questions chosen to help you make good impressions and lasting memories.

  1. Interesting conversation topics will take you down all kinds of paths, but they all lead to great conversations.
  2. Have your whole crew laughing with funny questions to ask.
  3. Normal is boring. Mix things up with these weird questions to ask.

How to Ask a Guy Random Questions: 2 Tips

Alright, you’ve got all these great random questions ready to go, the only thing left to do is ask them. To get the most out of your conversations, check out these two tips below.

1. Have a goal in mind

Think of these random questions as a means to an end, that end being an enjoyable chat with a friend. Choose the questions that will help you have the kinds of conversation you want to have.

2. Don’t over do it

random questions to ask a guy - Don't over do it

Randomness is fun, but too much randomness is hard for people to keep up with – like a toddler sprinting from room to room. Find the balance and your conversations will be much more meaningful.

In Conclusion

Random questions can be like a shot of adrenaline when a conversation starts to flatline. If you know the right questions to ask you can start deep conversations with old friends or get to know guys you’ve just met.

These random questions to ask a guy can serve any purpose you need them to, so go forth and have great conversations!