OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
Release Date: 04/21/2025
Suppressed, Rediscovered, Essential: Rav Kook’s Lost Guide for Modern Faith (262)
Orthodox Conundrum
This episode is partially a detective story, partially an analysis of daring ideas, and partially an invitation to discover new methodolgies of confronting challenges to Orthodox Judaism. Rav Kook drafted L’Nevuchei HaDor over a century ago—then the manuscript largely disappeared from view, resurfaced piecemeal, and sparked debates about redaction and “censorship.” In this follow-up to our popular episode with Professor Marc Shapiro, I speak with Rabbi Aryeh Sklar, translator of the new English edition, to unpack both the history of the text (why it was sidelined, what changed between...
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Learning Tanach Daily Through 929: Opportunities, Challenges, and Dangers, with Rabbi Benny Lau (261)
Orthodox Conundrum
As one 929 cycle ends and the next begins, Scott talks with Rabbi Benny Lau—founder of 929—about why the project started, what it hopes to change in Jewish life, and what a shared, chapter-a-day cadence can build across communities. They also tackle the harder questions: the risks of using Tanach as a direct guidebook without the mediating lens of the Oral Tradition, how to engage ethically with challenging passages, and where pluralism meets red lines. Practical takeaways included: how beginners can start this week, and what to do when you fall behind. Whether you’re all-in on 929 or...
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Orthodox Parents and Their LGBTQ Children, with Rabbi Yakov Horowitz (260)
Orthodox Conundrum
When a child shares something deeply personal about his or her sexual orientation, Orthodox parents can feel love, concern, and uncertainty all at once. In this conversation, Rabbi Yakov Horowitz reflects on what he’s learned working with families and communal leaders: how to approach the first conversations, which words can prevent hurt, and where halacha and mesorah guide our choices. We also consider what he’s heard from senior rabbinic figures, how different communities navigate these moments, and what hope might look like over time. This is a tender, honest discussion meant to help...
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When Mitzvot Lose Their Meaning: Rabbi David Stav on Reconnecting Orthodox Youth to Jewish Law (259)
Orthodox Conundrum
Why do so many young Modern Orthodox and National Religious Jews embrace the community but drift from halacha? In this episode of Orthodox Conundrum, Rabbi David Stav, head of Tzohar, joins Scott to confront the growing gap between identity and observance. Together they tackle the hard questions: Are we teaching halacha in ways that feel lifeless and irrelevant? Has secular society — from college to army service to technology — reshaped how youth see mitzvot? And most importantly, how can parents and educators reignite passion for Torah and halacha, showing a new generation that Jewish law...
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The Bible, the Beasts, and the Big Lies About Israel, with Rabbi Dr. Natan Slifkin (258)
Orthodox Conundrum
From biblical lions to the bizarre “Zionist crocodile plot,” Israel’s wildlife tells a story that shatters modern anti-Israel myths. In his new book Lions of Zion, Rabbi Dr. Natan Slifkin reveals how the animals of the Land of Israel — past and present — reflect the Jewish people’s deep, indigenous connection to their homeland. Scott and Rabbi Slifkin tackle false narratives about “settler colonialism,” “greenwashing,” and cultural appropriation, and explore how creatures like sunbirds, jackals, and even poppies have been weaponized in the propaganda war against Israel....
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Disagreeing Like Moses: A Torah Blueprint for Conflict Resolution (257)
Orthodox Conundrum
As we approach Tisha B'Av — a day that mourns the devastating consequences of internal strife and baseless hatred — we must ask: is there a Torah model for constructive conflict resolution? Rabbi Alex Israel joins Scott to explore a striking example in Bamidbar chapter 32, where Moses engages the tribes of Reuben and Gad in what Rabbi Jonathan Sacks called, "a model illustration of positive negotiation and conflict resolution." What does this biblical conversation teach us about how to mediate conflict, preserve unity, and build a stronger community — even when we disagree? Scott and...
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Must Every Jew Be Shomer Shabbat? A Fresh Perspective on Kiruv, with Rabbi Simi Lerner (256)
Orthodox Conundrum
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...
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Overeating, Obesity, Ozempic, and Orthodox Jews, with Dr. Sharon Grossman (255)
Orthodox Conundrum
Obesity is now responsible for more deaths in the United States than smoking—yet the Orthodox Jewish community rarely addresses it as either a public health emergency or a halachic concern. In this eye-opening episode, Scott speaks with Dr. Sharon Grossman to explore the medical, hashkafic, and halachic dimensions of obesity, overeating, and eating disorders. They discuss startling statistics about caloric intake on Shabbat, whether extravagant kiddushes and wedding meals reflect a violation of Torah values, and how halacha approaches issues like achilat gasa, guarding one's health, and...
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Will Charedi Society Face Reality? Dayan Yehoshua Pfeffer on Work, Faith, and the Future of the Torah Community (254)
Orthodox Conundrum
Is the Charedi community prepared to confront the demands of real life—economic, civic, and national—or has it built a worldview that prizes withdrawal over responsibility? In this provocative and thoughtful episode, Dayan Yehoshua Pfeffer joins Scott to explore what happens when religious ideology collides with practical reality. Drawing on his influential Sapir essay and other writings, Dayan Pfeffer explains how parts of Charedi society have defined religious life through a lens that minimizes human effort and places near-exclusive trust in divine outcomes—an attitude that discourages...
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Faith, Prayer, and the Impossible: Rabbi Shlomo Brody on Emunah, Miracles, Reality, and the Power of Tefillah (253)
Orthodox Conundrum
In the wake of Israel’s stunning victory over Iran—an event many have called miraculous—Jews around the world are reflecting on the nature of divine intervention and the power of prayer. Can we, and should we, pray for miracles? In this deeply thoughtful episode, Rabbi Shlomo Brody joins Scott to explore the halachic and emotional dimensions of tefillah in desperate times. What does it mean to ask for something that defies natural law? Is there a spiritual cost to praying for impossible outcomes? And how should we respond when a loved one is terminally ill—when a cure seems impossible,...
info_outlineThe Orthodox Conundrum Podcast is off this week, and we'll be back next week with a brand new episode. In the meantime, enjoy this classic episode about Orthodox Jews who leave Orthodoxy.
There’s a phenomenon in the Orthodox world which is called by various names, though most commonly “Off the Derech” or OTD, and “Datlash,” short for “Dati Leshe’avar” - that is, formerly religious. For a community which prides itself on continuity and on passing the tradition from one generation to the next, the idea that people leave Orthodoxy is simultaneously painful and threatening. Why did he or she leave? What didn’t work? Why don’t they see what I see… or perhaps, if we’re being truly honest with ourselves, what do they see that I may be missing? And when the people who reject an Orthodox way of life are members of our family, the difficulties are compounded.
Rabbi Alex Israel has given a lot of thought to this issue and these questions, and his insights are humane, generous, and rooted in Torah. Rabbi Israel and Scott spoke about whether the terms OTD and Datlash - and even “dati,” religious - are helpful or misleading, whether the phenomenon of people moving away from Orthodoxy is becoming more common, how it may be different in Israel and in the United States, whether we should actively try to bring those who have left Orthodoxy back into the Orthodox fold, if an emphasis on dogma is partially to blame, how parents should navigate having a child who is less religious than they are, what we can learn from those who leave Orthodoxy, and more.
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