The *Real* Secret To Great First Date Conversation

Stephen Hussey


That’s it. You can stop reading now. See you next week!

Seriously though, people always wonder how they can be fascinating company, and all it really requires is the ability to ask good questions.

Yes, you can learn about art, have travelled widely, and display a nauseatingly high level of expertise about fine wines. Knowledge might make you seem intelligent, but it won’t necessarily make people LOVE having conversations with you.


What really gets other people fascinated is how much you make them think. How much they feel their brain stimulated and opened up from sharing thoughts with you.

And the way to do that is by what you ask.

For example:

  • “What is the #1 quality you would want your children to have?”
  • “If you could have a painting of one person on your mantelpiece ,who would it be and why?”
  • “What is your most underrated personality trait?”
  • “Would your rather be super clever or super attractive?”
  • “What book or movie would you recommend to every 18 year old?”

When you ask the right questions, you can wake up parts of people’s brains that usually remain asleep through so much of their everyday lives. You get to be someone who encourages them to discover ideas and opinions they never even realized they have.

And the best part?

You don’t need any excuse to ask these things. Just go ahead. Say, “I heard the most interesting question today” and then ask it.

I’ve talked about plenty of deeper conversation techniques in other posts on this blog. But I’ve noticed time and time again how my favorite people to talk to in life are often those who set my imagination ablaze simply by probing a part of my brain with the right question.

Try it next time you’re stumped for conversation, or even try it someone close to you. Google “interesting questions in conversation”, pick a few from the top results, and ask them to your best friend (just add some context, so they don’t think you’re taking a survey).

You’ll be stunned at how much you can learn about people you thought you already know inside and out just by giving their imaginations some new juicy meat to chew on.

What’s your favorite question to spark fascinating conversation? Let me know in the comments below!

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