You shouldn't even be thinking about it. That's how things get awkward or forced. You don't wanna turn it into an interview or interrogation lol.
Just let conversations flow and the questions will come naturally. But good conversation starters are simple ice breakers, like "so what kind of music you like? Because I just love ______" or if you're at a pizza place, ask him what's his favorite topping on a pizza, which will lead to a story about his sister and pizza, then the convo leads to more natural questions. And that's the simple version of Hopeless Romantic class. Good luck miss thing!
