Orthodox Conundrum

Scott Kahn

Details

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 forward in the areas at which it excels, and to rectify the areas that need improvement.

Recent Episodes

OCT 5, 2026
What's the Point of God If God Doesn't Intervene? With Rabbi Yitz Greenberg (306)
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! What's the point of God if God doesn't intervene? Rabbi Yitz Greenberg has spent more than sixty years wrestling with the meaning of faith after the Holocaust, and one of his central claims is that God increasingly expects human beings to take responsibility for the world rather than waiting for divine intervention. But if that's true, what role does God actually play? And what does it mean for covenant, religious obligation, and prayer? In this conversation, we discuss Rabbi Greenberg's understanding of Judaism as a religion that demands that we "choose life"; why he has significantly revised his famous idea of the "voluntary covenant"; why he believes God's increasing hiddenness represents not divine absence, but a more mature stage in the relationship between God and humanity; and what all of this means for the relationship between Orthodox and non-Orthodox Jews. We also discuss one of his more controversial claims: that Christianity may itself be part of God's plan for bringing the biblical message to humanity. And finally, I ask what prayer means in a world where God increasingly leaves the work to us. When we ask God to heal, to provide justice, or to repair what is broken, are we asking God to act, or are we accepting responsibility to act on God's behalf? This is a wide-ranging conversation about God, Torah, the Holocaust, religious pluralism, Christianity, human responsibility, and what faith means in a world where God may not intervene in the ways that we expect. Listen to the new Naaseh weekly podcast! Each week, host Ari Levisohn, joined by Rav Jeremy Tibbetts or Lazar Berman, starts with a close reading of the Parsha and asks what happens when we try to actually live it - not only in our own lives, but in the communities we create - and the kind of society we're trying to build. Because Torah isn't only meant to describe a better world. It's meant to help us build one. The Bereishit episode of Naaseh is out now. Find it on Spotify, Apple Podcasts , or YouTube. Rabbi Yitz Greenberg just released his new two volume set of classic essays, Life Against Death. Listeners to Orthodox Conundrum in the United States and Canada will receive a 40% discount, and a 50% discount for bulk purchases of ten or more copies of the set. Just go to JPS.org, and include the discount code 6AF26 for a regular purchase, and discount code 6LIFE2V50 for orders of ten copies or more. 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 [email protected] 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 [email protected] to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
77 MIN
SEP 23, 2026
Living in the Sukkah: What Halacha Really Requires, with Rav Chayim Soloveichik (BONUS EPISODE)
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! What does it actually mean to make the sukkah our home for seven days? In this special bonus Sukkot episode, I speak once again with Rav Chayim Soloveichik, this time about the practical halachot of sitting in the sukkah: when to say leishev basukkah, which foods require eating in the sukkah, working and sleeping in the sukkah, dealing with heat, rain, and other discomforts, traveling on Chol HaMoed, and much more. Along the way, Rav Chayim explains why the goal isn't simply to determine when we're technically obligated to be in the sukkah, but to embrace one of the most unusual and beautiful mitzvot of the year. Talli Rosenbaum and I have just released Intimacy and Sexuality for Emerging Adults, powered by Intimate Judaism - a new ten-part podcast series designed to give young Jewish adults the kind of honest, thoughtful and Torah-based guidance about relationships, sexuality, and intimacy that too many of them simply aren't getting. We talk about emotional intimacy and vulnerability, dating and physical boundaries, attraction and sexual desire, anatomy and sexual response, consent and communication, pornography, love and marriage, niddah and building intimacy within marriage, some of the difficult questions surrounding sexual orientation and Torah, and more. All ten episodes of Intimacy and Sexuality for Emerging Adults are available now; just click here to get it on Spotify or Apple. 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 [email protected] 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 [email protected] to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
55 MIN
SEP 14, 2026
Emphasizing the Good: A Solution or Part of the Problem? A Conversation with Rabbi Judah Mischel (305)
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! As Yom Kippur approaches, we naturally think about what's wrong: our failures, our mistakes, and the ways that we, and the Jewish community as a whole, need to change. Rabbi Judah Mischel challenges us to pay attention to something else as well: the nekudah tovah, the point of goodness in ourselves, in other people, and in the Jewish people. He argues that focusing on what's going right, magnifying it, and building upon it can be a far more effective path toward growth than constantly emphasizing what's wrong. I find that idea deeply inspiring. But I also struggle with it. Because sometimes things really are wrong. Sometimes people are hurt. Sometimes communities develop unhealthy patterns that desperately need to change. And if we become so determined to emphasize the good that we hesitate to call out the bad, are we encouraging growth, or are we actually becoming part of the problem? In this pre-Yom Kippur conversation, Rabbi Judah Mischel and I wrestle with these questions while also discussing the extraordinarily difficult, and extraordinarily hopeful, moment in Jewish history in which we are living. We talk about optimism and realism, judging people favorably, confronting wrongdoing, criticizing communities without condemning them, and how we can work toward meaningful change without losing sight of the tremendous good that already exists. As we approach Yom Kippur, perhaps the challenge is not to choose between seeing the good and confronting the bad, but to figure out how to do both in a way that actually makes us, and the Jewish community, better. Talli Rosenbaum and I have just released Intimacy and Sexuality for Emerging Adults, powered by Intimate Judaism - a new ten-part podcast series designed to give young Jewish adults the kind of honest, thoughtful and Torah-based guidance about relationships, sexuality, and intimacy that too many of them simply aren't getting. We talk about emotional intimacy and vulnerability, dating and physical boundaries, attraction and sexual desire, anatomy and sexual response, consent and communication, pornography, love and marriage, niddah and building intimacy within marriage, some of the difficult questions surrounding sexual orientation and Torah, and more. All ten episodes of Intimacy and Sexuality for Emerging Adults are available now; just click here to get it on Spotify or Apple. 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 [email protected] 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 [email protected] to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
62 MIN
SEP 7, 2026
Does Orthodox Judaism Have a Fear Problem? Rethinking Religious Anxiety Before Rosh Hashanah, with Rabbi Dr. Judah Goldberg (304)
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! Fear can be a powerful religious motivator. It can push us to repent, reinforce commitment to halakha, and help communities maintain standards from one generation to the next. But what happens when fear becomes part of the culture of Orthodox Judaism itself? As Rosh Hashanah and Yom Kippur approach, Scott speaks with Rabbi Dr. Judah Goldberg about the anxiety that often accompanies the Yamim Noraim, and about what that anxiety may reveal about Orthodox life throughout the year. They discuss the hidden messages we transmit through education, the role of charismatic religious authority and Daas Torah, whether our fear of losing religious commitment causes us to rely too heavily on fear itself, and what it would mean to build a religious culture grounded instead in love, trust, awe, and a secure relationship with God. But there is a genuine risk on the other side as well: if we deemphasize fear and stress God's unconditional love, might commitment to halakha suffer? This is a conversation about much more than how to feel differently on Rosh Hashanah. It's about what motivates Orthodox Jews, what kind of relationship with God our communities are trying to create, and what we might gain, or lose, if we choose trust over fear. Talli Rosenbaum and I have just released Intimacy and Sexuality for Emerging Adults, powered by Intimate Judaism - a new ten-part podcast series designed to give young Jewish adults the kind of honest, thoughtful and Torah-based guidance about relationships, sexuality, and intimacy that too many of them simply aren't getting. We talk about emotional intimacy and vulnerability, dating and physical boundaries, attraction and sexual desire, anatomy and sexual response, consent and communication, pornography, love and marriage, niddah and building intimacy within marriage, some of the difficult questions surrounding sexual orientation and Torah, and more. All ten episodes of Intimacy and Sexuality for Emerging Adults are available now; just click here to get it on Spotify or Apple. 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 [email protected] 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 [email protected] to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
70 MIN
AUG 31, 2026
A New Chareidi Party Challenges the Status Quo: The Draft, Daas Torah, and Israeli Society, with Rabbi Yitzchok Adlerstein (303)
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 Chareidi draft issue has become one of the most contentious questions in Israeli society, and the established Chareidi political parties have largely presented a united front: protecting the existing system and opposing efforts to draft Chareidi men into the IDF. But a newly formed Chareidi political party, HaTzibbur HaChareidi, is offering a very different approach. Its platform says that those who genuinely devote themselves full time to Torah study should be protected and allowed to continue learning, while those who don't should serve the country in some capacity. But the party's challenge to the Chareidi status quo goes well beyond the draft. It argues that many working Chareidim, Chareidim who have served in the army, and those who want greater participation in Israeli society are no longer adequately represented by the existing Chareidi political establishment. Rabbi Yitzchok Adlerstein is supporting HaTzibbur HaChareidi, and in today's conversation we discuss what this new party stands for and whether it has a realistic chance of changing Chareidi politics. We talk about the draft, who should qualify as a full-time Torah learner, whether yeshiva attendance should be monitored, Chareidi service in the IDF, Daas Torah, government funding, and the relationship between Chareidi society and the State of Israel. Rabbi Adlerstein describes the party's vision as a "new old Yiddishkeit." The question is whether that vision can offer a genuine alternative to the Chareidi political status quo. Talli Rosenbaum and I have just released Intimacy and Sexuality for Emerging Adults, powered by Intimate Judaism - a new ten-part podcast series designed to give young Jewish adults the kind of honest, thoughtful and Torah-based guidance about relationships, sexuality, and intimacy that too many of them simply aren't getting. We talk about emotional intimacy and vulnerability, dating and physical boundaries, attraction and sexual desire, anatomy and sexual response, consent and communication, pornography, love and marriage, niddah and building intimacy within marriage, some of the difficult questions surrounding sexual orientation and Torah, and more. All ten episodes of Intimacy and Sexuality for Emerging Adults are available now; just click here to get it on Spotify or Apple. 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 [email protected] 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 [email protected] to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
68 MIN