There was a group who brought boys from non-religous families for a Shabbaton to the last Yeshiva I was in, and they asked a couple of bochurim to learn with them during the seder. I agreed to try it out. In the little talk they gave us beforehand, they asked us NOT to debate philosophy with them, NOT to spend time on Hashkafah, but to concentrate on the sugya of our choice.
The first twenty minutes was an absolute waste of time. Much as I tried to make it stimulating and interactive (we did the sugya of Chayecha Kodmin; I spoke about Euthanasia, Life Support Machines, Abortion…) he wasn’t interested; he spent more time looking around the Beis Hamedrash than listening to what I had to say. After approx. twenty minutes, he interrupted and asked me if I was married. When I said no in a surprised voice – I was still seventeen, I realized it was time to close the Gemara.
He told me he “always wanted to have one of those heart to heart talks with someone, but never knows how to start”. Eventually, he opened up, and we had a riveting discussion about Life, the Universe, and Everything. It was highly stimulating, intellectual, and eventually, personal. The organizer of the event came around to see if everything was okay, and was standing behind us listening to the conversation. He told me afterwards that he didn’t mind that I was debating with the boy – he normally doesn’t allow it because he isn’t sure the Yeshiva bochurim are up to successfully navigating the conversation on safe waters, but after listening to our conversation he gave me “permission” to continue our discussion.
What I want to know is this: The professional Kiruv experts all say that the best way to be mekarev is through learning Lomdus with them, not through talking about their issues. In all the times I helped in this program, I found the opposite to be true. I understand that the professional trained Mekarvim may have more success in that area, but as far as amateurs are concerned, I found the opposite.
Has anybody ever found more success in learning a gemara with an absolute beginner (who couldn’t finish of the Pasuk “Shema Yisroel H’ Elokeinu H’ _______”!) than starting with Hashkafah?