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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12 Replies to “The *Real* Secret To Great First Date Conversation”

  • If you could go forward & attain one of your passions in life…What would it be…and what is holding you back from doing it?? That’s my question Stephen…I think it is a great “brainal” question… ;) <3
    Great article…as usual! Keep them coming…I love reading them…

  • It’s amazing when you start talking to someone you find fascinating, and they are clearly sparked by you, how much their looks become partly inconsequential. I find it a magical thing in life when this happens.
    I would want any child of mine to be able to ‘think outside the box’ meaning they are not afraid to forge their own path and not be a sheep.
    The book and movie without a doubt War Horse. Michael Murpurgo’s books are wonderful, this one is so resonant for young lives today. Which is why such an accomplished Director made it into the most emotional, important film.
    There are many more graduates in the world today, lots of super clever people. And there are a range of products and procedures to make the most average looking of a person relatively attractive. A person who can be playful, witty and bright with a beautiful smile and compassionate nature, and who carries themselves with confidence and grace is surely to be admired.
    It’s no wonder you like someone with whom to spark a deeper fascinating conversation as you are super bright and need the stimulation. I live in hope, ‘ a triumph of hope over experience’ !
    Great article Stephen, Kate xx

  • Dear Steven,

    You Are an inspiring writer keep going!!!
    One of my favourite questions is “if you couldn’t fail and everything would work out the way you’d want it to and you wouldn’t be afraid of the success what would you Do?”

  • I loved the first question.”What is the #1 quality you would want your children to have?” I beleive people always the best for their children. Also it will be a good chance to know if they wish to have a family and children in the first place.

    Note: I started following you recently.

  • I quite like the fun one of ‘Would you rather….” too. Google them, there are some great playful questions to ask

  • very simple: a)Is there anything or anyone that rocks your world ? (getting to know passions)
    b) has it ever happened to you to envy someone of sth. like a talent or a quality that you don’t have?

  • Thanks for sharing these, they are great conversation questions! I have several but the one I like best is “What do you respect most about a woman”?

    I’ll let you interpret the question Matthew

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