10 (Really Deep) Conversation Starters for Anyone who Hates Small Talk // 2019 Edition

A couple of years ago I wrote a post with 10 conversation starters for anyone who “hated” small talk. After another couple of years of listening to podcasts, reading books, and watching content (mostly centered around question asking), I’ve come across 10 more questions I’d like to share.

This is for all of you who love to dive into the deep, the intense, the joyful, and sometimes the messy when it comes to conversing with people you care about. The next time you’re hanging with close friends, out to dinner with family, or want to throw a new acquaintance for a loop, try throwing one of these questions into a conversation and seeing where it leads. 🙂

10 (Really Deep) Conversation Starters for Anyone who Hates Small Talk // 2019 Edition

1. What’s one thing you know for sure?

2. What is one thing you are afraid people will find out about you? (Something you avoid telling people, at least at first)

3. What’s the most difficult decision you’ve had to make (to fulfill your destiny)?

4. How would you describe your childhood?

5. What keeps you up at night?

6. When is the last time you cried?

7. What is one thing you like doing that makes you feel the most free, alive, or full of joy?

8. How do you like to play? What are your hobbies?

9. What is your dream job? Or what is one thing you want to accomplish before you die? How are you pursuing that?

10. What makes you angry? What makes you cry?

Once again, thank you to the original question-askers who inspired this blog post (Oprah, Rob Bell, Liz Gilbert, Laura McKowan, Meadow DeVor, Lewis Howes, and others I am sure I am forgetting right now!).

Happy Chatting. 🤓

xo, Bibs

Photo by Laszlo Kiss on Unsplash

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