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 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

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

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.

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 Rabbi Israel then apply these lessons to modern conflicts that divide the Jewish people in Israel and around the world. This episode offers a timely and hopeful message: disagreement doesn't have to lead to division, and conflict can become a source of growth — if we learn to listen, negotiate, and speak with respect. 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. 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! To read my article on Jewish Unity from last month, click here. 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

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/. 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

Dr. Sharon Grossman, a Harvard-trained radiation oncologist and expert in halachic medicine, joins the discussion on obesity within the Orthodox community. They tackle shocking statistics on caloric intake during Shabbat and how traditional meals can lead to overeating. The conversation covers the ethical considerations surrounding weight loss surgery and medications like Ozempic, addressing their implications in both health and Jewish law. Grossman advocates for a balanced approach to body image and self-care, urging a healthier relationship with food and wellness.

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 participation in Israel’s workforce, civic institutions, and national service. But is this mindset sustainable in a modern state? And how do Charedi thinkers reconcile it with halachic sources, economic necessity, and lived experience? Scott and Dayan Pfeffer also delve into the social, theological, and ideological obstacles to change—particularly the way certain ideas have become "untouchable" within the community. Can Charedim pursue professional careers, engage with broader society, and still maintain fidelity to Charedi identity? Or does such a shift inevitably bring them closer to the Modern Orthodox world? This is a challenging, respectful, and essential conversation for anyone concerned about the future of Torah Judaism in Israel and throughout the world. 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

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, but giving up feels like betrayal? They also tackle a more uncomfortable question: Does excessive reliance on prayer risk becoming a substitute for human responsibility—such as voting, civic engagement, or taking necessary action in the real world? Can asking God for a miracle ever become a way of avoiding the hard work of confronting reality? This wide-ranging and nuanced conversation explores how to balance faith, hope, and the knowledge that God can do anything, with realism and the recognition that He has discouraged praying for that which is outside the realm of possibility; when to pray for mercy instead of outcomes; and how to maintain emunah without falling into magical thinking. It’s essential listening for anyone grappling with what it means to live—and pray—with integrity in the face of uncertainty and crisis. Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 20 is especially relevant today - you can find it on Spotify or Apple Podcasts. 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

When the United States bombed Iran’s nuclear sites this week, the Middle East—and the world—entered a new phase of conflict. In this urgent episode, Scott speaks once again with Yaakov Katz, former editor of The Jerusalem Post, about what these strikes mean for Israel’s war effort, the potential consequences of regime change in Iran, the risks of escalation, and how this moment may redefine the geopolitical landscape. This is essential listening for anyone who wants to understand what’s really happening beyond the headlines. Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 20 is especially relevant today - you can find it on Spotify or Apple Podcasts. To preorder While Israel Slept by Yaakov Katz, click here. 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

Two Israeli embassy staffers shot in Washington. Jewish activists burned in Boulder. A mayoral candidate in New York who refused to condemn the Holocaust gaining momentum. Antisemitism in the United States is no longer hiding in the shadows — it’s on the march, in broad daylight. In this urgent bonus episode of Orthodox Conundrum, Scott Kahn speaks with Rabbi Chaim Steinmetz and Andy Weiss about the troubling rise in antisemitic violence and rhetoric, the mainstreaming of hate, and how American Jews are responding — with concern, activism, and a growing sense of alarm. From Zohran Mamdani’s alarming candidacy to the broader cultural shift that’s making Jew-hatred acceptable again, this is a frank and timely conversation every Jew needs to hear — whether or not you live in New York. 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