‘Know-them-better’ – 30 Questions to know their hues!

Getting to know someone can be a nerve-wracking process, sometimes. Most of us have a few different versions of ourselves, based on who we’re interacting with. The more put together version usually comes out informal or new settings, while the real you pops up around familiar and/or people you connect with. Discovering a new person can be a very exciting process if you set the trail to that journey well.






Here are some questions that can help you in such times and keep the awkwardness and small talk at bay!

  1. What would you do in life if you didn’t need money to survive?    

This is a gateway to understanding where someone’s heart lies.    The world we live in today dictates more actions of our than ever before. Talking about being free of these cuffs can give you a glimpse of what a person would invest in if there were no rules.

  1. What’s a great weekend like for you?

Always a great question when you’re trying to understand someone’s likes and dislikes. What someone chooses to do over a great weekend says a lot about what’s necessary for their peace of mind and their idea of fun and/or calm.

  1. What was the hardest thing you ever had to do?

Hardship is a bittersweet part of being a human being. While it’s tough to power through, overcoming hardships and looking at them in hindsight provide a sense of accomplishment and capability like nothing else.It’s a very personal experience and sharing that with someone who barely knows you can be a powerful way to connect.

  1. Where do you belong?

The Stage! A farm! Flying high in the sky!   Where someone is right now isn’t necessarily where they belong.This is a great way to know where the person feels most himself/herself.

  1. What’s your favourite book? 

Books are the doorway to a person’s personality. Figuring out which story moves someone and why can tell you a lot more about them than you’d expect.

  1. What music will be on the playlist of your life?

Music connects people in ways conversation can’t pull off! Finding someone who introduces you to great music or someone who has similar or unique taste in music is a very interesting way to connect.

7. What would be the name of your autobiography?

How someone looks at their life is more about experiences than the actual events taking place.Learning about how someone would name their journey so far will show you their trials, temptations and aspirations in one go.

  1. What’s the most common misunderstanding people have about you?

This is a great way to know someone well. We’ve all been subjected to opinions we don’t relate to ourselves. It’s an off-beat way to know the intricacies of an individual.

  1. If you could change one thing about yourself overnight, what would you change? Why?

There’s always room for change! Everybody is perfect in their own way and all, but come on! We all want something different from what we have, in our lives. Ask this and watch their imagination go wild with how and why they would ask for something different.

  1. What’s your fondest childhood memory?

Childhood is an important phase in everyone’s life. Try taking a glimpse at where someone has been, what made them who they were and what feelings they associate with reminiscence.

  1. What’s your favourite season and why?

Nature has its grip on all of us in some way. Rain, snow, sun or fall, one of them has our heart. Figuring out which season someone likes is a great way to explore the depths of an individual. Do they like chilly weather to cozy up, does fall bring more hope than despair or if the sun shines right through them!

  1. If you could meet a famous person dead or alive, who would it be?

For me, it HAS to be Michelle Obama. She signifies hope, strength and grace. She’s everything I aspire to become.

Being able to meet a star we look up to, is connecting with a person who is part of our aspirations, they are everything we hope to be.

See how much you know about me after this question?

  1. What was the last experience that made you a stronger person?          

This is a great question to ask. As the listener it makes you sound interested in really knowing the person, rather than engaging in small talk. It also lets the person feel like you understand that they’ve been through things in life and have learnt and triumphed all of that and are now standing in front of you. Without even trying, you’ve let the person feel connected to you like they can trust you like you “just get it”.

  1. What’s your favourite movie?

Movies make us feel the whole range of the emotional spectrum in 120 minutes. Great movies have the ability to provide hope and comfort and yet it’s a different one for everyone. We all know that there’s nothing quite like finding someone who loves the same movies! (or better ones)

15. When is the most nostalgic you’ve ever felt?Nostalgia has got to be the most human feeling ever. Most often things that make us feel nostalgic often have a deeper emotion underneath. It’s bitter-sweet, it’s one-of-a-kind and it’s the most personal possession as a human being. It can be a person, place, scent, touch or emotion. Accompany someone on a journey back in time when time itself stood still.

  1. At 60, what do you want to have achieved more than anything else?

Ambition is the driving force of mankind. Throwing in this question helps you understand the person’s ideal state of the world.

17. If not here, where would you like to live for the rest of your life, why?  “If we were meant to stay in one place, we would have roots instead of feet”.  A new/ different place can mean a lot of things. Our surroundings can play a vital role in our endeavours. Discover what a place means to them and see a new world through their eyes. 

  1. What is the one food item you can never have enough of?

Good food can flip a bad day. Connect on cuisines, dishes and flavour. They say the way to a person’s heart is through the stomach.

  1. Who do you look up to?

People in this category serve as subconscious north stars. Knowing who someone looks up to will tell you a lot about their needs.

  1. How do you want to be remembered?

We all want to leave a legacy behind to be remembered by. Get someone talking about this and they’ll open up to you like a blooming flower!

  1. What was your greatest achievement and what did it do to you?

Who doesn’t like to talk about their triumphs? Take the time to understand how experiences change people, how highs and lows make the contours in every life.

  1. Do you believe people are inherently good?                                                               

Beliefs are the most common foundation of an individual’s life. How one views humanity and people can speak volumes about his relationships, his experience with the world and his approach to the connection as well. The question unifies the talker and the listener as belonging to the same race, bringing in a sense of belonging. The people having the conversation take a look at the rest of the race, as if looking in from outside, providing an idea/opinion based on what they see and their interpretation of it.

  1. What is love?

This sure is an interesting one. It’s what shapes so many of our years in its various forms. Learn about different perceptions of love, share yours and explore this fuzzy concept.

  1. What’s your favourite of the day?

Sunrise, sunsets, dusk or dark- each signifies a feeling. How the person interprets each day, which part they look forward to and what they use it to do is an interesting conversation filler.

  1. What’s the smell you love the most?

Often associated with nostalgia, scents and smells can invoke strong feelings. It brings back memories and emotion associated with it. Sharing a nostalgic moment with someone can be a great way to make a moment stand out.

  1. What is the craziest, most outrageous thing you have done/ hope to do in your life?

A goof resides in all of us and comes out from time to time. Letting lose and throwing caution to the wind can be liberating experiences. Often these moments make the best stories to by narrated over the years. Share some crazy and laugh out loud at loud each other’s madness and watch the connection unfold between you two.


  1. What makes you cry?

Whether you can cry at the drop of a hat or not, we’re engineered in a way to feel deeply about something in this world. Crying is a vulnerable experience and the beauty of it is that it brings you just a little bit closer to those you bare them in front of.

  1. What makes you the happiest?

It’s the most sought-after state of being. We dream of things that can make us happy, we actively invest in getting as close to being happy as possible. Talking about what makes you happy can leave you feeling good even just for the moments you talk about it. Sharing this part of your needs with someone can be therapeutic in its own way.

  1. If you could dedicate your life to solving one problem what problem would it be?

A sense of purpose keeps us going everyday in a world that can be quite ruthless in its ways. Find out what they’re passionate about, what makes their wheels churn and heart thump.

  1. What’s your favourite way of spending time alone?

Solitude is a mirror that helps you see and know yourself. How people choose to spend this time says a lot about where their mind is and what their needs are.

A connection is an important aspect of being human. Some of us have a flair for it, while some others need a hand in being able to bond with others. These are but a few suggestions for questions to help facilitate conversation, but questions aren’t as important as being a good, active listener.  Make that person the focus of attention while diving beneath the surface of general socialization.

The conversation can change dramatically when you focus your attention on the other person, hold eye contact, and offer an inviting smile. People respond well when your body language demonstrates that you care about what they have to say. It’s not enough to ask the right questions here and there. No one wants to feel like an afterthought or that they do not deserve focus!

Be prepared to answer some questions about your new friend too. No one enjoys a stagnant one-sided conversation. Bonding requires a certain degree of vulnerability from both parties.


Get out there and unleash the listener in you. The world has a lot to offer and you can start with meaningful interaction!

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