First couple of dates are pretty much school, yeshiva, Israel stories, family, work, college…
Third date is like the first 2 but more relaxed. And you can have the music/movies conversation. What you do and the hashkafic reasons behind it. But other than that, don’t get too into hashkafa until the fourth date.
Fourth date you can talk about where you’d want to live, what kind of home you want to build…
Fifth date you talk about all the whys from the date before.
Sixth date you should already try to be opening up more- maybe saying something a little more personal or something that might make you feel vulnerable.
And then from there you really shouldn’t have to plan conversation.
When I dated, there were a couple of guys (including my husband) that on a 5th or 6th date, when we were really comfortable with one another, we’d just have question asking time. Like anything we were curious about, we asked. Those dates were always the best for me because it initiated some really amazing conversations and if you’re willing to be honest, it helps make a more personal connection.