What is kiruv really about—and what should it be about? In this thought-provoking conversation, Scott speaks with Rabbi Simi Lerner, a kiruv professional who challenges conventional assumptions about Orthodox Jewish outreach. They explore the core goals of kiruv, the philosophical and ethical pitfalls it can fall into, and how to ensure it respects the dignity and autonomy of every individual. Is the point to make people religious? Should every Jew be Shomer Shabbat? What happens when outreach causes regret—or even harm? They also discuss whether kiruv professionals objectify people, the bad habit exhibited by some kiruv professionals (and the problem with having "kivurv professionals"), and how to navigate halacha with integrity in the face of complex realities. Rav Simi emphasizes that many kiruv workers do tremendous and holy work in a careful and sensitive manner... and others do not.

This is a candid and essential conversation about one of the most idealistic—and sometimes problematic—projects in the Jewish world.

Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 89 is especially relevant in the days leading up to Tisha B'Av - you can find it on Spotify or Apple Podcasts.

Links for Rav Simi Lerner:

Judaism From Within Podcast

Two Rabbis, Three Opinions Podcast

Horeb: Philosophy of law and observances from Rav Samson Raphael Hirsch

Classes on Kuzari at Yeshivat Darche Noam

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.

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Music: "Happy Rock" by bensound.com