Yekke2 – I had friends who did kiruv in Russia years ago. They said that the boys’ program was much better than the girls’ program because they actually learned.
I am wondering if this rule (about learning Gemara vs. hashkafa) depends on the particular population one is dealing with.
Russians are known to be very intellectual, plus this was a generation ago. Ask any seminary teacher who has been teaching for 20 years and they will tell you that today’s generation is very different than the generation 20 years ago. No one has the ability to concentrate or to think anymore, so teaching is much more difficult.
Today’s generation tends to be less intellectual, have more emotional issues, and is more in need of warmth.
So maybe this principle used to be true, but doesn’t apply today to the same extent. It also may depend on the age of the student.
This is just a hypothesis. You also may be right that there is a difference between a kiruv professional and an amateur. I think the bottom line is that people have to do what they are comfortable with.
Also, is it possible that what they mean is that you should start with learning Gemara and you should not be the one to bring up hashkafa but if that is the direction they want to go in, you should discuss it with them?
ZD’s theory also makes sense and fits with what the organizer told you. If you were a 17 year old Yeshiva bochur, it makes a lot of sense that he was nervous about your getting into a hashkafa discussion with someone not-yet-Frum – both about what he might tell you as well as what you might say to him – both could be major causes of concern.