How about some questions about how he spends his time bein hazmanim, where did his family go during family vacations when he was growing up, anything to get him thinking outside the box of yeshiva. Some boys have a hard time remembering that the girl is not his chavrusa and that he’s not in yeshiva. It’s good that you like him, now you just have to see what you have in common. You’d be surprised but not all black hat boys have the same goals and they’re definitely not all the same.
