The Absolute Best Conversation Prompts
I guarantee it.
For my book on building social connection and IRL community, I’ve given A LOT of thought to how to foster deep connections through meaningful conversations. It’s often hard to break out of superficial small talk, so this week, I’m giving you my DEFINITIVE list of ground-tested, tried and true icebreakers and prompts guaranteed to spark connection and meaningful conversation among a wide range of people. This is the result of years of research and reporting and ideas that have worked so well in my own life, so I hope you enjoy it!
Who are more annoying, cat people, dog people, or parents?
Why do people send their children to private school?
Between you and your partner, who is the better parent?
Which religion do you think is the worst?
Why don’t you have more black friends?
What is your most traumatic memory?
How much did you buy your house for?
Which dietary restriction do you think is the most made-up?
Limited to just people we know, who would you like to cheat on your spouse with the most?
What’s the worst thing about being burned alive?
What’s one idea you have that sounds racist but is actually true?
How much do you weigh?
Lol just kidding, April Fools! Please never use any of these prompts, but I hope you had a laugh, because while I’m oh-so-earnest about community building and connection, I still have a sense of humor.
If you like my weird sense of humor, enjoy this parody of a summer camp instruction email.
Important Reminders for Your Child’s Upcoming Week at Camp LadyGulch!
(Your regularly scheduled How to Find Your People Club programming will be back next week (Paying members can catch up here!) but I had to reshare one of my all-time favorite newsletters as those of us with school-age children face down the the logistical and financial gauntlet called “summer camp” here in the US.
Feel free to suggest your own absurd icebreakers and conversation prompts in the comments below (and tell me how far you got into the list before you realized it was a joke.)
Stay tuned for next week when we kick off our block party month content!!! I’m especially excited about Vanessa Elias, founder of Block Party USA, joining us for a members-only Zoom conversation on April 22nd at 1PM EST. Become a member so you don’t miss out
And don’t forget, I’m running a 25% off yearly membership discount until April 10, So get it while it’s hot.






Still crazy after all these years ❤️
Dude. I 100% fell for this! Even after checking the pub date before I started reading!!