Hilari had a series of ice-breaker questions she used on first dates.
Ever slept with a guy?One night when she was supposed to be mid-date, she appeared in my apartment, planted face-down on my bed without using her arms to break her fall, and started convulsing. His answer to her warm-up question, she finally managed to say, was "complicated." I didn't dare ask which question she'd asked. Does it matter?
Ever done time?
Say, you don't have a latex allergy, do you?
Do you have an aversion to hairy, inverted nipples?
When I'm getting to know someone, I do nothing so clever. I ask about their biggest heartbreak. I find nothing more illuminating. This cuts to the quick of who someone really is. If they've been crushed, they've likely learned to respect others' feelings. The finest empathy fertilizer, after all, is minced heart. The nature of the crushing, too, is informative. What did they learn? Was it easy to see coming? Were they enablers? Procrastinators? Or was it the full-on, life-altering body-slam of complete surprise? And if they've never had their heart broken, that's exceedingly valuable information. This person is probably the crusher, not the crushee. If they aren't serial users, they merely leave before letting anyone get close.
A great question, that. My old reliable. Got one of your own? Share.