20 Random Questions to Get to Know Someone

By on December 7, 2013

Meeting and getting to know someone new can be a daunting and nerve-wracking experience. You want to find out important things about them, without turning a casual conversation into an interrogation with lots of serious questions. You also don’t want to be caught in an awkward silence, desperately thinking of something witty to say. When the small talk has run try, try asking some random questions to spice things up. Although some of them may sound silly, random questions can give you a unique insight into the personality and preferences of another person. Below we’ve chosen 20 Random Questions to Get to Know Someone that you can work into your conversation when speaking to someone new.

1.  Where would your dream holiday be?

The answer to this question can tell you how adventurous someone is – maybe their dream holiday would be backpacking and hiking in Peru, relaxing in an island paradise, or living it up in a bustling, exciting city like New York. You can also share stories about your travels, and places you’d like to visit before you die.


2. What sound do you love?

This question requires a bit of thinking, and you may be surprised at the answer. Maybe your new acquaintance loves the sound of a Ferrari engine, or acoustic guitar music, or even the theme song to their favourite TV series. Whatever the answer, you’ll have a new and interesting topic to discuss.


3. If you were a dinosaur, what kind of dinosaur would you be?

This quirky question is bound to get a smile, if not a confused face or a nervous giggle. Break the ice with a silly, funny question that shows your sense of humour, and you’ll put the other person at ease.


4. If you could be any fictional character, who would you choose?

Katniss, Bella Swan, Harry Potter? This question gets you talking about your favourite books and movies, and you can find out a lot about the other person’s preferences. You might even reveal a secret passion or pastime!

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5. If you were a super hero or super villain, what powers would you have?

This is a sneaky way to assess the morals and secret fantasies of your new friend. Do they want powers to help humanity? Would they use their powers to play practical jokes or punish their enemies?


6. If you could breed two totally different animals together, what new animal would you create?

This question is great for finding out if your acquaintance like animals – and, how creative they are! Prepare yourself for some hilarious and bizarre answers, and interesting conversations about weird creatures.

7. What other languages can you speak?

This is a fact that people don’t usually share for fear of sounding arrogant. However, if you ask this question when speaking about travel, you may find out about your new friend’s family background, education, and whether they enjoy travelling.


8. Do you love or hate rollercoasters?

The answer to this question can tell you how adventurous someone is – if they’re terrified of rollercoasters, chances are they won’t be up for adventure sports or a day out at a theme park!

9. Whats the weirdest thing you’ve ever eaten?

Find out how adventurous (or brave!) someone is by asking them about the most unusual thing they’ve ever eaten. You can also talk about food you like and don’t like, and let the conversation flow naturally from there.


10. Do you collect anything?

This question helps you to find out if your acquaintance has an interesting hobby or passion – maybe they collect stamps, or bottle caps, or football paraphernalia. You may even be able to bond over a shared interest!


11. What would be in your dream sandwich?

Everyone loves talking about food, and describing your ideal sandwich is a great way to get the conversation started. Keep in mind what they food they like so that if things go well, you can suggest somewhere nice for your next meeting.


12. If you could meet anyone, living or dead, who would you meet?

Alternatively, you could ask who they’d invite to a dinner party if they could invite anyone, living or dead. You might find out who their role-models are, who they admire, and why they’d like to meet them – valuable information if you’re trying to get to know someone better.


13. What was your favorite cartoon growing up?

Bugs Bunny, Dexter’s Laboratory, The Animaniacs? Chat about things that you miss from your childhood, your favourite Disney movies, and cartoons that you loved watching on TV. Who knows, you might share a love for Tom and Jerry!


14. What’s the coolest thing you’ve ever been for Halloween?

This is a fun and lighthearted question to keep the conversation interesting and topical. You may just be surprised by the answer!


15. What’s the best gift you’ve ever received? 

This is a great question to ask if you’re curious to know what really matters to someone. Was their best gift something personal and sentimental, or something expensive and flashy?

16. What ice-cream flavours do you love/hate?

This is a simple question to see if you have similar likes and dislikes. The answer doesn’t matter all that much, but debating the best ice-cream flavour can be fun!


17. Are you a dog person or a cat person? 

Instead of asking, “Do you have pets?”, ask if they prefer dogs or cats, and why. Their reasoning can reveal a little bit about their personality – maybe they prefer cats because they are independent and aloof – qualities they may admire.

18. What’s your fondest childhood memory? 

Lighten the mood by speaking about happy memories from your childhoods. This way you can learn about his or her background without prying.


19. Would you rather be poor and happy, or rich and miserable? 

The answer to this question will reveal a lot about someone’s priorities – whether they value happiness over money, and whether they’d compromise their happiness to be rich. Something worth thinking about.

20. What would be your ideal first date? 

If you’re thinking about starting a romantic relationship with someone you’re getting to know, asking them about their ideal first date make them think about what it’d be like to date you!


Hopefully you’ll be able to have a great conversation with your acquaintance, and through using these questions, learn a lot more about them whilst creating a closer bond between the two of you.

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