(1 - not at all, 5 - on all foods) 800 Questions to Ask A Girl 1000 Questions to Ask your Boyfriend Are you a "dogperson" or a "catperson"?
What is the most distant place you've visited (from your home)?
Wet the toothbrush or brush dry with the toothpaste?
Who is the first person you call when you have a bad day?
Do you ever doubt the existence of others than you?
Have you ever collected stickers that are on fruits?
Consider popping a few of these questions on your next first date and see where they lead the conversation. What do they wish they could have done differently, if anything? You don’t have to rapid fire interrogate someone, of course, but it can lead to a conversation about their past that’s meaningful but still light. This isn’t meant to prompt a confession of your date’s failures. What about you, what do you wish you were better at? This question will let your date show their vulnerable side, and admit to something they’re not entirely comfortable with, particularly if you chip in first to show solidarity.
That said, bring them up when there's a lull in the conversation or you're bored; you have nothing better to do than talk anyway, right? Is your middle finger longer than your ring finger? What time do you normally go to bed on a working day? What would you want to be written on your tombstone? When you looked in the mirror first thing this morning, what was the first thing you thought? How many rolls of film do you need to get developed?