Like lots of other introverts out there, small talk is a struggle for me. I stress out about initiating conversation and find vapid chats about the weather painfully boring. Which is why I've used this column as something of a catchall for advice on better small talk, including icebreaker questions to get the conversational ball rolling. 

Little did I know that someone else was way ahead of me. Via the excellent Hurry Slowly newsletter I recently learned The Art of Noticing author Rob Walker has been collecting dozens of great, offbeat icebreaker questions in a giant, publicly accessible Google doc

It's a goldmine for small talk phobics like me, so if you're one, check out the entire thing, but here to get you started are a bunch of fun suggestions: 

  • What's the worst prediction you ever made? Walker confesses he left Titanic absolutely sure it was going to be a colossal flop. I distinctly remember a friend trying to explain how the internet would revolutionize everything to me back in the early 90s and completely not getting how that it was more than just a fun toy. Everyone has a story and most of them are interesting. 

  • If you weren't doing your current job, what would your dream job be? This option, which is ideal for professional settings, was suggested by a reader. Walker says he'd be a radio DJ. I want to do something completely offline like raise goats and make artisanal cheese. What's yours? 

  • What question do you wish people would ask you? Why try to puzzle out what the other person wants to answer? Just ask. Brilliant. 

  • What is your earliest memory? "I think it can work with not only with someone you just met, but someone you've known for ages," notes Walker. 

  • Tell me something about yourself that I could never tell from looking at you. The teacher who recommended this one for the list explained "it leaves the option of going deep, but the person answering really has control over how exposed they want to be."

Intrigued? Check out the complete doc for literally dozens more. 

Published on: Mar 18, 2020
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