20 Interesting Questions to Ask to Get to Know Someone – LIFESTYLE 101’s


College life got over way back. Doesn’t mean you can’t get to be knowing new people. Interacting with strangers for lack of a better word or getting to know more and more people is what adds to our own spectrums, broadens our horizons and perspectives.

Be it a formal setting with your co-workers, a date, or a social gathering – we’ve all been there. Rattling our brains for the next smart thing to say to escape that God forsaken awkward silence.


First off. Breathe IN Breathe OUT.


The key to making interesting conversations you’re looking for is interesting questions. Questions that actually show your interest in the other person’s story and getting to know them.

Listen intently. But don’t just sit there nodding your head like a psychopath. Asking questions doesn’t mean it has to be a one way conversation – Participate !




1. If you could commit a crime and get away with it – what would it be ?

The fun part comes in getting the free bail card. Exploring the other person’s dark side and to what they would do in a social setting.


2.  What’s your story ?

It’s playful. It’s intriguing. You sound genuinely interested. And you get to hear the highlights of the other person’s life.


3.  If you could live forever, how would you ?

Questions like this – you don’t really think about them. Once you do ask them, you get the other person’s gear running.

They’re forced to think and look deep down into their desires.


4.  If you could travel anywhere in the world – where would it be ?

Another great ‘what if’ question that gets people to think where they are the happiest. The one’s who say “Here” should always stay in your life no matter what.



5.  You’re stuck on a deserted Island – You can get three things with you. What would they be ?

Another back to the wall situation where you can see what people rely on a do or die situation. Do they play based on their emotions, sentiments, or rationality.


6.   If you could change one law, one ingredient in the society, what would it be ?

Good thought provoker.


7.   Which are you likely to fight for Money or Love ?


8.   If you could get to fight a celebrity one on one . Who would it be.

Much a la Fight Club. Light, playful, and a vent !



9.   Mountains or Beaches ?

Definitely two kinds of people. Mountain lovers and beach lovers. Which one are you talking to ? Find out .


10.   Would you rather stay in the city or the woods ?

Simple question, yet powerful enough to give you a glimpse into what the other person wants.


11.    If everyone in the world was your audience for 5 minutes, what would you say to them ?


12.    What makes you cry ?



13.    If you had a week to live, how would you spend it and why ?

You can add whom would you want to spend it with as well.


14.    Would you rather see your future or go back into your past ?

One question that gets people thinking. Whatever their response is, you can follow up with a Why always.


15.    If you could eat something without putting on the calories, what would your favourite cheat meal be ?

Light, playful, and getting them to talk about their guilty pleasures. All in my friend.


16.    What would you do if you were to meet your 15 year old self ?

This is something you can ask yourself as well. A very interesting scenario to imagine yourself in.



17.     If you could date any celebrity for a day, who would it be ?

One life. Why not ?


18.     If you could go back to the era of a ruling empire, which one would you choose.

Also gives you a chance to see the other person’s awareness of history.


19.     What’s your fondest childhood memory ?

And I’m sure a little part in all of us still wants to go back and live that moment. Fond memories.


20.    If there was a Zombie apocalypse, how would you survive it ?

That’s deep. And you get to see a lot about the other person’s survival instincts.



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