Orthodox Conundrum

Orthodox Conundrum

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The Orthodox Conundrum is a forum in which we look honestly at the Orthodox Jewish community, identifying what works well and what does not, so that, through an honest accounting, we can find solutions that will be successful. We will examine some of the major issues that affect the Orthodox world, without exaggeration, whitewashing, or pretending that they don't exist. Our hope is that the Orthodox Conundrum will spark wider discussion that will enable Orthodox Judaism to continue moving...
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Episode List

What You Really Need to Know About the Three Weeks and the Nine Days, with Rabbi Chayim Soloveichik (297)

Jul 6th, 2026 12:00 AM

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and members get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! Every year, as the Three Weeks begin, the same questions come up. Can I listen to music? Go to a baseball game? Buy new clothes? Shave? Go to movies? Travel? The answers may surprise you. In this episode, Rabbi Chayim Soloveichik joins me for a practical discussion of both the meaning and the laws of the Three Weeks and the Nine Days. We begin by exploring the ideas that underlie this period of mourning before turning to the practical halachot, clarifying what is actually prohibited, what isn't, and where different customs exist. Whether you've always wondered about a particular practice or simply want to make sure you're observing these days correctly, this conversation offers a clear, thoughtful, and accessible guide to one of the most significant periods on the Jewish calendar. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). If your business is interested in advertising to our engaged Orthodox audience, or if you'd like to sponsor an episode in honor of a loved one or simcha, please reach out to aliza@jewishcoffeehouse.com to support meaningful Jewish conversations. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Should Yeshiva Students Serve in the IDF? The Torah Case for Saying Yes, with Rabbi Menachem Copperman (296)

Jun 29th, 2026 12:00 AM

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and members get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! Last week on the podcast, Rav Shaya Karlinsky presented the case for broad draft deferments for full-time yeshiva students. This week, we continue that conversation by hearing a very different perspective. My guest is Rav Menachem Copperman, who argues that military service is not merely a civic responsibility or a practical necessity - although it is certainly those, as well. He believes it is a religious obligation rooted in halachah, Jewish morality, and the Torah's demand that we take responsibility for one another. In our conversation, we discuss whether Torah study can ever justify exemptions from military service, whether the IDF has done enough to accommodate religious soldiers, the relationship between Torah learning and national responsibility, the meaning of leadership and religious authority in this debate, and what both the Religious Zionist and Haredi communities can learn from one another. Whether you agree with Rav Copperman or not, he presents a thoughtful, passionate, and deeply Torah-based vision of why he believes more yeshiva students should serve. As with last week's episode, my goal is not to tell you what to think, but to help you better understand one of the most consequential debates facing Israeli society and the Jewish world today. As always, I hope this conversation challenges you to think more deeply and more carefully about an issue that affects us all. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). If your business is interested in advertising to our engaged Orthodox audience, or if you'd like to sponsor an episode in honor of a loved one or simcha, please reach out to aliza@jewishcoffeehouse.com to support meaningful Jewish conversations. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

The Chareidi Draft Debate: Is Common Ground Possible? with Rav Shaya Karlinsky (295)

Jun 22nd, 2026 12:00 AM

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and members get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! The debate over Chareidi military service has become one of the most contentious issues in Israel today. It touches questions of national responsibility, Torah study, religious freedom, political power, social cohesion, and the very nature of the Jewish state. Since October 7, those questions have only become more urgent - and they are at the forefront of the current crisis in both Israeli government and society. In this episode, I speak with Rav Shaya Karlinsky about how we can resolve the current impasse between much of the Chareidi community and the rest of Israeli society. We talked about the relationship between the Chareidi community and the IDF, the role of full-time Torah study in Israeli society, and what a workable long-term solution might look like. Rav Karlinsky argues that full-time Torah learners should continue receiving deferments, that Chareidim who are not learning full time should serve, and that the state must create and maintain frameworks that genuinely accommodate Chareidi religious commitments. I suspect many listeners will agree with some of what Rav Karlinsky says and disagree with other parts. I certainly do. But regardless of where one stands, I believe that serious conversations require us to listen carefully to views that challenge our own, and I hope this discussion contributes to that effort. Among other topics, we discuss whether Israel can maintain a world-class Torah community while meeting its military needs, why distrust has become such a central obstacle in this debate, the future of Chareidi service in both the army and sherut leumi, and what a healthier relationship between different sectors of Israeli society might look like. This is not a debate. It is an attempt to understand a perspective that is often discussed, frequently criticized, and rarely heard in its fullest form. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). If your business is interested in advertising to our engaged Orthodox audience, or if you'd like to sponsor an episode in honor of a loved one or simcha, please reach out to aliza@jewishcoffeehouse.com to support meaningful Jewish conversations. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Why Return to Israel If Judaism Can Thrive Anywhere? Lessons from the First Exile, with Yael Leibowitz (294)

Jun 15th, 2026 12:00 AM

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! Last month on the Orthodox Conundrum, I spoke with several guests about the relationship between Israel and the Diaspora. We discussed questions of aliyah, Jewish peoplehood, covenant, sovereignty, and the role of Diaspora communities in an era when most Jews may soon live in the State of Israel. Today, I'd like to revisit that broader conversation from a very different perspective with my guest, Tanakh educator Yael Leibowitz. Rather than beginning with today's headlines or contemporary debates, she takes us back to the destruction of the First Temple, the Babylonian exile, and the return to Israel. Her argument is that many of the questions we are wrestling with today first emerged more than 2,500 years ago. How could Judaism survive outside the Land of Israel? Why return if Jewish life could flourish elsewhere? What responsibilities do Jews in the Land and Jews outside the Land owe one another? And what does it mean for a people to maintain both a homeland and a Diaspora at the same time? Drawing on the books of Yirmiyahu, Yehezkel, Ezra, Nehemiah, Esther, and others, Yael shows how exile transformed Jewish life and identity, while also explaining why the Land of Israel remained central to the Jewish story. This is not a conversation about contemporary politics. It is an exploration of the origins of one of the most important debates in Jewish life, and why that debate remains so relevant today.  For more of Yael's writing visit: yaelleibowitz.com. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). If your business is interested in advertising to our engaged Orthodox audience, or if you'd like to sponsor an episode in honor of a loved one or simcha, please reach out to aliza@jewishcoffeehouse.com to support meaningful Jewish conversations. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Intimacy in an Age of Anxiety and Uncertainty: How Chronic Stress Changes Relationships (CO-RELEASE WITH INTIMATE JUDAISM)

Jun 8th, 2026 12:00 AM

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/! Instead of a regular episode of the Orthodox Conundrum Podcast, we're releasing a new episode of Intimate Judaism, which is dropping on that channel today, as well. We hope you find this episode meaningful. We'll be back next week with a brand new episode of the Orthodox Conundrum. October 7 changed countless lives. But for many Jewish people across the world, the deeper challenge has been what came afterward: months and years of ongoing stress, uncertainty, grief, and vigilance. In this episode, Talli Rosenbaum and Rabbi Scott Kahn explore how chronic stress affects relationships, intimacy, and sexuality, and why connection remains one of our most important sources of resilience and healing. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). If your business is interested in advertising to our engaged Orthodox audience, or if you'd like to sponsor an episode in honor of a loved one or simcha, please reach out to aliza@jewishcoffeehouse.com to support meaningful Jewish conversations. Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast.

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