Ever found yourself struggling to find the words in the company of a complete stranger? For that matter, what do you say when the guy sitting beside you on a bus happens to be a friend of a friend? Sometimes, you might just fancy a guy or you come across someone who would love to know. But initiating a conversation with strangers is not always easy for everyone. We totally get it. Which is why we put up a bunch of random questions that you can ask a guy you have just met, or a guy you are interested in.

To begin a conversation with a guy, and to get to know him a little bit, there is a wide range of questions that you could ask him.

So, what are you waiting for? Ask away!

1. If your five year old self would be here right now, what would you like to warn him about?

This could very well get emotional and very personal. But that’s the whole point anyway. Would be great to learn about his perspective.

2. What is the word in English that is always spelled incorrectly in every single dictionary?

What? It’s not that hard, come on! Incorrectly, silly!

3. There’s a boat full of people but you cannot spot a single person on board. How do you think that’s possible?

Alright, let me tell you then. It’s because all the people on the boat are married!

4. Tell me how many months have twenty eight days?

Did you say February? Nope. All the twelve months!

5. What has a thumb and four fingers but doesn’t have a life?

Gloves, obviously!

6. When was that one time when you overslept and woke up to find twenty missed calls from your parents who completely freaked out?

This is a question that, in most cases, has a funny yet scary story following up!

7. If you were to morph two animals and create one super animal, which ones would you choose and why?

Elephants and rabbits, tigers and giraffes, horses and cats – there’s so much that you can imagine and put up together just to have a laugh!

8. Which movie, if made into a musical, would perhaps sound the funniest?

Come on, it could be anything!

9. How would you explain something to somebody without mansplaining?

This is going to get really interesting!

10. Someone fell off a fifty-foot ladder but still did not get hurt! How come?

Well, they fell off the bottom rung!

11. What’s a five letter English word that becomes shorter when you add two letters to it?

If he’s not the brightest bulb, just don’t let him sell himself Short.

12. What’s the weirdest thing you’ve said or done to escape a disastrous date?

Does your sibling save you, or your best friend?

13. Have you ever sent a text mistakenly to your boss/teacher that was meant for your best friend?

This could go wrong in so many insanely unimaginable ways!

14. What’s something that can be caught but not thrown away?

If he’s smart he’ll say “A cold”. If he’s spontaneous he might make up something interesting.

15. Forwards I am heavy and backwards I am not. What am I?

The answer is a ton, and that’s just how much fun riddles can be as conversation starters.

16. If you had to pick between going to school everyday or working half-day on every weekend, which one would you choose?

This one might need some thinking. Would probably depend on whether it was his school life that was more fun or his work life.

17. What do you think is the craziest combination of food that people eat?

While most people would probably say pizza and pineapple, there might be crazier combinations out there that you have no clue about!

18. What’s the one thing that isn’t a crime but you wouldn’t mind getting arrested for?

Hopefully he will use this opportunity to flex his brains.

19. Which one would you rather choose and why – a tattoo on and around your nose or on and around your lips?

This could get really funny, or really bizarre.

Useful: Would You Rather Questions for Adults

20. What’s the most embarrassing thing you’ve been caught doing?

There could be a hundred stories that would come up the moment you ask some of these questions, and the rest depends on the two of you.

21. What’s something that others are scared of but you aren’t?

Could be some high cliff, or even some ghost he befriended. Let’s just hope it isn’t the latter for your sake at least.

22. What is the most bizarre rumour you have heard about yourself?

We all hear rumours! You don’t have to feel embarrassed.

Now that you’ve come across multiple random funny questions to ask a guy, go ahead and open up! Strike a conversation and a good laugh, and get to know a stranger better. Have fun!

Click here if you want more random questions!