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Positively Speaking: 15 Questions To Get The Conversation Going

Ever been stuck in a social situation where you have no idea what to say? Or been at a party where you find yourself asking (or being on the receiving end of) the same old boring 'small-talk' questions?

The Brits are terribly polite when it comes to social conversations and usually stay well clear of 'personal' questions.

It's probably why we are well known for discussing the weather. No one feels offended or put on the spot when you are talking about drizzle, sun, lack of sun, or that last storm that blew down Mr Smith's old oak tree and decimated your fence panels. It's 'safe'.

But I think it's time to for a small-talk revolution. Here are 15 questions* guaranteed to get the conversation going and help you connect more deeply with the person you are speaking to:

The Past

1 - If you could change anything about your upbringing or childhood, what would it be?

2 - What's the most embarrassing moment in your life? (Make sure you go first here!)

3 - What's your most treasured childhood memory?

The Present

4 - Given the choice of anyone alive in the world right now, which 3 people would you want as your dinner guests?

5 - What is your greatest accomplishment in life so far?

6 - What qualities do you value most in your friends?

7 - Before you make a phone call, do you ever practice what you are going to say? Why?

8 - If your house, containing everything you own, caught fire, after loved ones and pets, what's the one thing you would save? Why?

9 - What question do you wish someone would ask you?

The Future

10 - If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

11 - If you had a crystal ball that could tell you the truth about yourself, your life, your future, or anything else, what would you want to know?

12 - If you won the lottery jackpot, what's the second thing you would buy?

13 - If you were only able to listen to three songs (or pieces of music) for the rest of your life, what would they be and why?

14 - What would your perfect day look like?

15 - What skill do you wish you had? Why haven't you learned it yet?

Bonus question!

16 - If you were reincarnated as an animal (or were transformed into an animal), what would you hope to be? Why?

I hope you found these questions interesting, and that they enliven your social conversation and help you connect with people on a more meaningful level. Let me know which question is your favourite by emailing me at

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* Some questions adapted from Greater Good In Action's '36 Questions For Increasing Closeness'.


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