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 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…