Do you have an allergic reaction to small talk and bullshit? (I do.) 

If you do have such an allergy, work, especially working in an office, can be unbearable. Conversations range from banal (so, any plans for the weekend?) to completely hypocritical (‘Charlie’s idea is brilliant.” from someone who hates Charlie’s idea.)

Over the past decade every time I hear a good question I write it down. I now have a list of 25 questions that cut past bullshit. It’s like Conversational Claritin.

So, if you ever want to really know someone. Like really know them. Pick from this list. Please feel free to add new ones.

1. What’s the strangest date you’ve ever been on?

2. What’s the most trouble you ever got into in high school?

3. What’s the strangest thing you’ve ever seen on public transportation?

4. What’s your favorite, most outlandish item of clothing?

5. What characteristic in others causes you to feel envy?

6. Who’s someone you’ve lost touch with who you’d love to reconnect with?

7. When was the last time you woke up at 3 am and thought “I’m a fuck up and it’s all my fault?”

8. Describe a meeting when you wish you were wearing a wire. 

9. Is there a moment in which you kept your mouth shut and now wish you’d spoken up?

10. Who’s the most audacious/courageous person you’ve ever worked with? 

11. Who did you think you would be when you grew up - how are you different from that vision?

12. Describe a time when you felt you were doing the best work of your life? Why did it stop?

13. What of your own limitations has been hardest for you to make peace with? Why?

14. What trait in others is hardest for you to tolerate? Why?

15. What’s the hardest setback you’ve ever had to overcome? When you look back on it now do you regret going through it?

16. What’s the scariest thing you’ve ever done in your career?

17. What’s a mistake you consistently swear you’ll never make again? 

18. What’s your most irrational fear? What’s your most irrational calm?

19. What’s the most daring/exotic adventure you’ve ever embarked on?

20. Which celebrity or famous person do you think you’d become friends with if you ever got to know one another?

21. In what situations do you feel the most out of place?

22. Who is someone you think you owe an amends to?

23. What assumption do people make about you that is inaccurate?

24. How do you calm yourself down?

25. What situations cause you to beat the shit out of yourself?