20 Weird But Interesting Questions That Keep Me Up At Night


1. When and where was the first pillow fight?

2. If Jennifer Aniston knew I existed, would she find me attractive?

3. Are there more male or female dogs in the world?

4. Who was my grandmother’s best friend’s first kiss?

5. What percentage of the United States population has seen the inside of a federal prison but never actually been incarcerated?

6. Is it better to shower and then brush one’s teeth, or vice versa?

7. What is the best kind of cookie and why?

8. Why does my wife always answer my boyfriend’s texts before she answers mine?

9. If I were to beat Michael Jordan in a one-on-one game of basketball, which of the following would I feel most acutely: pride, suspicion, or guilt?

10. If all the snowflakes were candy bars and milkshakes, would the world really be that great?

11. How many licks does it take to get to the center of a diamond?

12. What is truly the best thing since sliced bread?

13. If I could live on any planet in the Solar System besides Earth, which would it be?

14. Which came first: brown, red, or blond hair?

15. If Chuck Norris died today, what would he do tomorrow?

16. Is it better to write in black ink or blue?

17. How many words have I spoken in my life?

18. How many people have I annoyed with my words?

19. If I were a woman, what would my name be?

20. Will I ever get a definitive answer to any of these questions?