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Where do you think technology that is ever-evolving will bring us? Are we truly alone in the universe? Is yogurt better than ice-cream? Should pancakes replace cakes for any event? Why does anything exist? Weird, right?

Why unorthodox questions? When getting to know someone, we tend to ask the same type of questions and give the same type of answers all the time. Think about it. You have done it. I have done it. Everyone does it. Conversations eventually get stale and die out.

Why do we converse in the first place? To get to know someone who seems interesting? To establish an emotional connection with someone you like? To obtain ideas and perspectives to aid our own position in this world? All of these things can only come out of engaging conversations with ideas that can have meaningful contributions.

Unorthodox questions help break the ice fast and cut to the chase quick. They can throw someone off from delivering their usual answer and make them be involved in the conversation. If someone’s first question to you was “What song have you fully memorized?”, wouldn’t you be curious and try to engage deeply in the potential conversation that follows?

Now I’m not saying that every exchange has to be deep and meaningful, but not every conversation has to be plain and routine. Questions like “If you were the dictator of any island, what crazy things would you implement?” or “If you can permanently change the flavour of celery, what would the flavour be?” can be fun and really let the conversation flow to wherever it may go.

Here are a few questions that you can try (along with the previously mentioned questions):

  • If you didn’t have to sleep, what would all that time be used for?
  • What is the one thing you want to unlearn?
  • If aliens did make contact, what do you think will actually happen?
  • Would you fight 10 duck-sized humans or 1 human-sized duck?
  • How would you describe colours to a blind person?
  • Which video game world would you live in?
  • If you can replace water with any other liquid/drink as an essential need for living things, what would it be?
  • What trend would you bring back?
  • What do you think your best find is?
  • Would you own 100 puppies or 100 kittens?

Armed with this arsenal of quirky questions, you can be sure that you and the other person will definitely be involved in amazing conversations!


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