If you are trying to get to know someone, be it a friend, a colleague or a love interest, it’s all about asking the right questions.

Sure, you want to make a good impression when you meet somebody. And being armed with conversation starters will help you achieve that. But digging deeper with insightful questioning will also allow you to build an authentic connection.

To help you make the most out of every convo, we’ve rounded up a list of questions you can use to break the ice, navigate a social situation, develop meaningful relationships and have great discussions ranging from fun and lighthearted banter to profound and insightful debates.

Basic ice-breakers

What is your favorite food?

If we have learned anything from Instagram, it’s that everyone really likes to know what other people are eating. Finding out that you both loathe mayo or love pickles can be a simple way to bond during a first interaction.

Do you like to travel?

People who love to travel have stories to tell, and they love to share those stories. And it will get you to know the person really fast without asking a super personal question on your first meeting. Traveling entails dealing with the unexpected and getting out of your comfort zone, and the way a person approaches situations like these is telling.

What are you reading/watching?

If the national mourning that happens after a major character’s death on This Is Us is any indication, people get really into their favorite shows. The same thing can be said about movies and books. If there’s a movie they just saw that you saw too, that’s instant conversation.

What is your favorite drink?

This one can easily sound like “May I buy you a drink?” so timing is everything! If they are really into wine and you’re not, you can ask them questions about enhancing your wine-tasting experiences. And if they don’t drink alcohol at all, this can also reveal more about their values and interests.

Do you have any pets?

Anyone who has pets will open up like a fountain in no time. You’ll be looking at photos of their cat in a Santa suit within minutes. And who knows, you may just end up planning a dog park date in the near future.

Questions to ask someone to get to know them better

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What do you want to be when you grow up?

(Perfectly fine to ask someone who is already well above voting age.) This is also great to find out whether the person is passionate about their current careers.

What is your favorite thing about yourself?

It’s an interesting way to discover what makes someone tick, fast. It may also pull out a few insecurities, which leads to a vulnerable and honest conversation.

What is the most recent dream you have had that is still on your mind?

Dreams can tell a lot about someone’s personality. Plus, this is a perfect entry point into a deeper conversation about psychology and the subconscious.

What’s in your fridge right now?

It’s a bit more personal than a favorite food question, and will tell you about their lifestyle. Do they love to cook? Are their careers so busy that they live on takeout? Are they into dining?

What are you most proud of?

Maybe it’s work-related, maybe it’s the new deck they just built from scratch, or maybe it’s their college sports achievements. In any case, you’ll know instantly more about what they value the most in life.

What risks do you think are worth taking?

This is a fascinating way to get a glimpse into someone’s head. Would they skydive in a heartbeat or do they see staying up past 10 p.m. as an adventure? It’s also interesting to hear about life risks that don’t fall into the realm of extreme sports and activities, such as quitting a job to become an entrepreneur.

What are you truly passionate about?

If you only get one question to get to know someone better, this should be it. It instantly takes the conversation to a no-BS level, especially in a work setting where you’re trying to break through the corporate walls and find out more about the person behind them.

What is the best advice you’ve ever received? The worst?

This will open the floodgates, good and bad.

What is the best advice you have ever given? What about the worst?

It may reveal a few regrets, but that’ll help you feel closer and share your own stories more easily.

Funny questions that will lighten the mood

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Which movie would be better as a musical? Or which musical better as a drama?

Just imagine the most dramatic movies out there, set to music and dancing. It can get hysterical! And you’ll quickly be able to assess how dark the person’s sense of humor is.

If you could learn any animal language, what would it be? Why?

Who wouldn’t love to know what their dog is saying? And if the person gives you a weird look, it may be an insight about their imagination and willingness to get a little silly.

What’s the weirdest thing in your purse/wallet right now?

You would be surprised about what people carry with them on a daily basis. And hearing the explanation will be even better.

Tell me your funniest joke.

This one is not really a question, but it will lead to an answer that will either be hilarious or not funny at all.

If you could start a cult, what would it be? And what would it be called?

If they already lead one, you may want to run.

Random questions that can lead to great conversations

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What can you cook?

Everyone has a special dish, and if you love food and entertaining you’ll enjoy discussing cooking techniques and ingredients.

Could you survive in the wilderness?

It’s always fascinating to find out whether a person has serious outdoor skills. If they do, they will most likely have tons of anecdotes to share about their adventures.

How many apps are in your phone right now?

This one may turn out to be impressive.

Which artists do you think are overrated? Underrated?

As long as you’re prepared not to get angry if they mention someone you love, this question can lead to great debates about music, film, art and culture.

 


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