A 40-something woman I’m friends with told me about a date she was on where the guy asked her what her favorite color was. She broke it off right then because, as she explained, at her age she had deep life experiences and if he was only interested in superficial crap like color preferences, they were incompatible. With that in mind, I collected a a cheat sheet of questions to ask your crush that can speak to your potential partner’s substance (or lack thereof). Or, at least give you something to talk about if it turns out you don’t have awesome conversation chemistry.

1. What is one thing you will never do again?

2. Would you rather be twice as smart or twice as happy?

3. What happened the last time you cried?

4. What happened the time in your life when you were the most nervous to do something?

5. What would your parents be surprised to learn about you?

6. What’s your worst habit?

7. What superpower would you have for one day?

8. What fictional character do you have the biggest crush on?

9. Where would you live if you could live anywhere in the world?

10. What is your most bizarre pet peeve?

11. Who knows you the best?

12. What after school activities did you do in high school?

13. What “most likely to” superlative would you be most honored to receive?

14. What’s the last book you really loved?

15. What was the greatest television show of all time?

16. What’s been your favorite age so far?

17. If you could go back in time, what is one piece of advice you would give your younger self?

18. What one thing would you be most disappointed if you never got to experience it?

19. Apologize or ask permission?

20. Unlimited love or money?