Orthodox Conundrum

Scott Kahn
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Nov 3, 2025 • 1h 7min

Charedi, Dati Leumi, Modern Orthodox, Traditional, Secular: Is Jewish Unity Even Possible? A Conversation with Rav Yosef Zvi Rimon (267)

Is Jewish unity even possible? In this urgent episode Rav Yosef Zvi Rimon faces the hardest questions raised by the draft crisis and by the widening gaps between Charedi, Dati Leumi, Modern Orthodox, Traditional, and Secular Jews. He explains why unity is not a slogan but a practical necessity and religious obligation with real consequences for security, community, and our shared future. With clarity and empathy he maps a path for principled disagreement, mutual responsibility, and practical steps that families, shuls, and schools can take right now. If you are tired of talking points and want a serious plan for healing rifts while staying true to conviction, this conversation is for you. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! 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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Oct 27, 2025 • 1h 3min

The World is a Beautiful Place... and We Need to Earn It: Talking About The Morning After with Dr. Erica Brown (266)

What does the morning after really look like... when the dawn reveals not only light, but rubble and work? In this deeply personal conversation, Scott and Dr. Erica Brown ask how we craft a vision of where we're going when optimism feels naïve, unity is fragile, and joy and grief insist on sharing the same space. Drawing on Rabbi Sacks's distinction between optimism and hope, they explore how to build active hope through autonomy, giving, and purpose. They define Jewish unity as purposefulness rather than groupthink, wrestle with isolation and rising antisemitism in the diaspora, and consider Rav Kook's "songs" of soul, people, humanity, and world in a time when many Jews feel pushed out of humanity's choir. Along the way, Scott reflects on grandparenting amid loss; Erica introduces the idea of "prophetic social justice" and the power of a "destination postcard"—a concrete picture of a better future; and together they share practical ways families can bind their children's wounds through volunteering and virtue. This is the morning after—honest, unsentimental, and stubbornly hopeful. Subscribe to Dr. Erica Brown's wonderful new Substack, Sacred Stamina, by clicking here. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! 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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Oct 20, 2025 • 1h 13min

Seven Facets of Healing: Rabbi Leo Dee's Blueprint for Jewish Resilience (265)

This episode is dedicated to the complete recovery of יהונתן איתן בן בת שבע ברכה. How do we move from private anguish to collective strength? In this deeply personal and wide-ranging conversation, Rabbi Leo Dee shares the story of the day his wife and two daughters were murdered, and the seven-facet framework he built to keep living with faith and purpose. We walk through Family, Friends, Fitness, Frumkeit (spiritual life), Function (purpose), Finances (trust and control), and Fun (simcha/growth)... first as practices for an individual in pain, and then as a national toolkit for a people living through ongoing trauma. Instead of drilling into tactics, we explore the principles that make the Seven Facets portable, from the home to the community to the nation: how language and presence matter, how practice can carry belief, how purposeful action restores dignity, how trusting what we can't control quiets anxiety, and how measured joy can coexist with memory. This episode is for anyone who refuses to let grief have the last word—and wants concrete, Torah-true ways to help themselves, their family, and Am Yisrael heal. Click here to order Rabbi Dee's wonderful new book, The Seven Facets of Healing. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! 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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Sep 30, 2025 • 1h 6min

Eulogies and Boundaries: Orthodox Jews and the Legacy of Charlie Kirk (264)

Charlie Kirk's assassination is a shocking, tragic act of violence. Murder is a desecration of the image of God, full stop. We condemn it unequivocally, and we pray for comfort for his family and for all who were harmed. At the same time, Charlie Kirk was a complicated public figure. He was outspokenly pro-Israel and often advocated for Jewish safety; he also voiced criticisms of Israel's current government. He advanced positions that many in the Orthodox world consider essential, and others consider deeply problematic. He defended Israel vigorously, and he also gave a platform to voices widely regarded as openly antisemitic. All of that can be true at once, and ignoring any part of that picture does our community no favors. In the days since his death, we've seen Orthodox individuals and organizations release statements ranging from restrained condolences to sweeping praise that some would call over-the-top. Today we're going to step back and ask, dispassionately and honestly: what should Charlie Kirk's legacy be for Orthodox Jews? This is neither a eulogy nor an indictment. Our aim is to slow the rush to hot takes and consider how a mature community remembers someone who meant very different things to different people. I have three guests on today's episode: Rabbi Yitzchok Adlerstein, Rabbi Benjamin Kelsen, and Rabbi Pesach Wolicki. Together we'll explore where they agree, where they diverge, and what that means for real life: how institutions and leaders speak publicly, and how we keep our disagreements from corroding relationships. Above all, we'll try to conduct this conversation in a way that is truthful, proportionate, and humane. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! 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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Sep 15, 2025 • 1h 16min

God's Loyal Opposition: Anger, Faith, and Divine Confrontation, with Rabbi Dr. Raphael Zarum (263)

Is it possible—maybe even Jewish—to be angry at God? From Abraham's challenge at Sodom to Job's cries of despair, Tanach is filled with voices that confront the Divine. But what does that mean for us today, when we struggle with personal tragedy, global antisemitism, and the ongoing pain of the seemingly endless war against Hamas? In this wide-ranging conversation on the Orthodox Conundrum, Scott Kahn speaks with Rabbi Dr. Raphael Zarum, Dean of the London School of Jewish Studies, about whether anger at God is heresy or a profound act of faith. Along the way, they discuss biblical protest, repentance, the Shoah, the morality of Israel's current war, the themes of Rosh Hashanah, contemporary crises, and whether confronting God can actually bring us closer to Him. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Sep 8, 2025 • 1h 12min

Suppressed, Rediscovered, Essential: Rav Kook's Lost Guide for Modern Faith (262)

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 versions, and who may have been protecting whom) and the ideas that make it urgent now: how Rav Kook navigates tensions between moral intuition and Torah; his approach to challenges from writings of the ancient Near East; why heresy can refine faith; his respectful stance toward other religions; and much more. As we approach Rosh Hashanah and Yom Kippur, we ask what this early, daring Rav Kook can offer a polarized 2025 about creative teshuva, intellectual honesty, and religious confidence without fear. Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, click here (Apple) or here (Spotify). Exclusive deal for Orthodox Conundrum listeners: code perplexed20 will give 20% off if they pre-order L'Nevuchei HaDor through kodeshpress.com. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Sep 1, 2025 • 58min

Learning Tanach Daily Through 929: Opportunities, Challenges, and Dangers, with Rabbi Benny Lau (261)

Rabbi Benny Lau, an influential Israeli rabbi and community leader, discusses the 929 initiative aimed at uniting Jewish communities through daily Tanakh study. He addresses the challenges of interpreting scripture responsibly, especially the risks of neglecting the Oral Tradition. Reflecting on his experiences, Rabbi Lau emphasizes the importance of connecting modern youth with their cultural roots. He also shares practical advice for newcomers and the emotional resilience gained through collective learning, showcasing Tanakh as a sustaining 'tree of life'.
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Aug 24, 2025 • 1h 7min

Orthodox Parents and Their LGBTQ Children, with Rabbi Yakov Horowitz (260)

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 listeners think carefully, speak gently, and consider their next steps with dignity—whatever they may be. Check out Tehillim Unveiled with Ari Levisohn and Rav Jeremy Tibbetts on Apple Podcasts or on Spotify - with a new three-part series on Tehillim 27, L'David Hashem Ori, dropping just in time for Elul! To contact Kesher Families, click here. Follow Rabbi Yakov Horowitz on Instagram - @yakovhorowitz and @brightbeginningsforum. We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Aug 18, 2025 • 1h 4min

When Mitzvot Lose Their Meaning: Rabbi David Stav on Reconnecting Orthodox Youth to Jewish Law (259)

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 is not just obligation, but a path to joy, meaning, and belonging? Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, click here (Apple) or here (Spotify). We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.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). 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. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Aug 11, 2025 • 57min

The Bible, the Beasts, and the Big Lies About Israel, with Rabbi Dr. Natan Slifkin (258)

Rabbi Dr. Natan Slifkin, founder of the Biblical Museum of Natural History and expert in biblical zoology, joins the conversation to debunk myths surrounding Israel and its wildlife. Their discussion reveals how animals like lions and sunbirds illustrate a deep connection between the Jewish people and their homeland. Moreover, they address false narratives around settler colonialism and cultural appropriation, exploring the historical ties of both Jews and Palestinians to the land and the intersection of natural history and contemporary political issues.

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