
Orthodox Conundrum
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.
Latest episodes

May 26, 2025 • 49min
From Beit Lechem to the Royal Ball: Comparing and Contrasting the Book of Ruth and Cinderella, with Rabbi Dr. Joshua Berman (249)
Megilat Rut — the Book of Ruth — is one of the most beloved and widely read books in the Hebrew Bible. Because we read it annually on Shavuot, many people are familiar with its basic storyline. But its very familiarity can sometimes obscure its most powerful messages. In this episode, I’m joined by Rabbi Dr. Joshua Berman of Bar Ilan University, who offers a fascinating lens through which to revisit Ruth’s story: the world’s most popular fairytale — Cinderella. By comparing the two narratives, Rabbi Berman uncovers striking parallels and, more importantly, profound differences that highlight essential Torah values. This conversation will change how you read Megilat Rut and offer fresh insight into the values that give Jewish life depth, direction, and meaning. Listen to the Tehillim Unveiled podcast here or wherever you find your 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

May 19, 2025 • 1h 15min
Can Physics Demonstrate God's Existence? (248)
Can science be a vehicle to get closer to God? The Rambam famously answered in the affirmative. In the second of the 1000 chapters of his Mishneh Torah, Hilchot Yesodei HaTorah chapter 2, the Rambam writes, “What is the method towards loving and fearing God? At the moment that a person investigates His wondrous and massive actions and creations, and sees through them His endless and infinite wisdom, he immediately loves, praises, and extols, and desires tremendously to know the great Name. In the words of David, ‘My soul thirsts for God, the living divine.’ And when he thinks about these things themselves, he immediately recoils backward and is awestruck and fears, realizing that he is a small, lowly, and beclouded creature, with minimal and superficial knowledge compared to God’s perfect intellect. As David said, ‘When I see your heavens… what is man that You should acknowledge him?’ According to these ideas I will clarify important principles of the works of the Master of the worlds so that they will be an introduction to one who understands in order to love God. As the Sages said with regard to love, from this you recognize the One who spoke and the world came into being.” The Rambam then proceeds to give an introduction to the Aristotelian world view that was presumed true in his time. While we no longer accept the Rambam’s science as accurate, his principle that knowledge of the universe is a vehicle to loving and fearing God remains an essential principle. What about using science to demonstrate God’s existence? The Rambam, again, was willing to use philosophical arguments for this purpose; but others recoil from the concept. Many people have no interest in examining theories such as intelligent design and creationism, and find them absurd. There’s a different but somewhat similar phenomenon which Professor David Shatz calls “bold concordism,” where scientists attempt to demonstrate that the first chapter of Bereshit and modern physics are in complete agreement, as long as the words of the Torah are read in a literal, albeit non-obvious way. Some people find this inspiring and helpful, while others dismiss it altogether. My guests today, Rabbi Aaron Zimmer and Rabbi Dr. Elie Feder, propose something quite different. They use established scientific facts based on up-to-date physics - scientific facts, that is, which no one denies - and argue that the most logical conclusion from this science is that the universe was created by an intelligent designer. This has nothing to do with the argument of intelligent design from biology, and is not based on any verses in the Torah. It doesn’t even deal with questions around divine providence or other aspects of Jewish belief. Instead, they argue that modern physics has offered a brand new and extremely compelling version of the argument from design: that the values of the constants are so unusual and so inherently unlikely, that the most obvious conclusion by far is that they were designed so that our complex universe, which includes atoms, molecules, stars, galaxies, and life, would come into existence. As they explain, almost all serious physicists were bothered by the problem of why the constants are what they are; physicists almost universally acknowledge that the reason that the constants have the values that they do is a huge mystery. Elie and Aaron only differ with most other physicists in that many others try to solve this mystery by positing the existence of a multiverse - that is, infinitely many worlds, each with different values of the constants; whereas my guests argue that this is far more unlikely than the obvious answer: that something with intelligence chose these constants for a reason. Regardless of whether you like the idea of using science to demonstrate God’s existence or disagree with the enterprise, Elie and Aaron’s argument demands serious attention. I’m honored to present it today, and look forward to hearing what you think. To learn more about Physics to God, to listen to the podcast, or to watch it on YouTube, 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

May 14, 2025 • 1h 4min
Having “The Talk”: How Should Jewish Parents Talk to Kids About Sex? (Co-produced with Intimate Judaism)
Please note that this episode discusses sensitive topics and uses explicit language. Listener discretion is advised. Today, the Orthodox Conundrum is releasing a new episode of Intimate Judaism that my Intimate Judaism co-host, Talli Rosenbaum, and I recorded with Yonina Rubinstein, where we explore how parents can approach conversations about sexuality with sensitivity, clarity, and confidence. How can we talk to kids about sex in a way that’s honest, healthy, and grounded in Jewish values? Yonina offers practical strategies for different ages and stages, explains the importance of modeling a positive attitude toward intimacy, and discusses how halacha and tradition can serve as a guide—not a barrier—to raising sexually healthy children. Whether you’re a parent, educator, or just thinking ahead, this episode offers an essential roadmap for both navigating and redefining “The Talk” in a way that’s both open and deeply rooted in Jewish life. This episode is being released simultaneously on Intimate Judaism and the Orthodox Conundrum. 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

May 12, 2025 • 22min
The Pope, the Jews, and Israel: What to Anticipate From Pope Leo XIV, with Dr. Malka Simkovich (BONUS EPISODE)
Last Thursday, Cardinal Robert Prevost of Chicago became Pope Leo XIV. While Jews may believe that this shouldn’t matter to us at all, this is most likely false. The pope commands the allegiance of well over a billion Roman Catholics worldwide, and his ability to help shape their opinions about the Jewish people and Israel should not be underestimated. To discuss what his election means for the Jewish people, and to review his predecessor Pope Francis’s record towards Jews and the Jewish state, I was honored to speak to Dr. Malka Simkovich. Malka has an interesting vantage point, as she is not only a well-known expert in Jewish-Christian relations, but she also spent ten years as the Chair of Jewish Studies at the Catholic Theological Union, which is where the pope studied in the early 1980s. This Tuesday night, the Orthodox Conundrum Podcast will release a regular episode - co-produced with Intimate Judaism - about how parents should talk about sex and intimacy with their kids. So look for that 48 hours after this bonus episode drops. 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

May 5, 2025 • 1h 20min
"You Can't Suppress the Light": The Radical Messages of Rav Kook for Orthodox Jews Today, with Professor Marc Shapiro (247)
The thought of Rav Avraham Yitzchak HaKohen Kook, who died in 1935, remains extremely influential today in religious Zionist circles. Rav Kook’s ideology, particularly as interpreted by his son, Rav Tzvi Yehuda Kook, in books like Orot, has helped to set the agenda for much of the dati leumi world. Over the past couple of decades, however, additional works written by Rav Kook have been published, and some of the ideas they contain are extraordinarily fascinating and at times radical, even as they often have little to do with the Land of Israel or Zionism. These ideas, far from being dated, speak to Orthodox Jews today and often palpably address areas that concern us in 2025. Rav Kook addresses issues such as the limits of Talmud study in forming the religious character of yeshiva students, the importance of establishing a broad curriculum of both holy and secular studies in yeshivot, the possibility that following Jewish law may not be the highest form of spiritual achievement, the wisdom of the masses that at times supersedes that of scholars, the place of natural law and innate morality when it contradicts our understanding of the Torah, whether certain narratives in the Torah need to be taken literally or even may use the prevailing scientific assumptions of those who received the Torah in order to convey a deeper message, the possibility that other religions may be divinely inspired, and much more. I’m encouraged by thinkers who move boldly in directions that others are reluctant to go; the combination of absolute commitment to God, Torah, and the Jewish people alongside heroic courage and honesty is both indispensable and atypical. Both in terms of his ideas, and in his willingness to ask questions, Rav Kook embodied this commitment and courage, and can serve as a role model for Orthodox Jews today. For that reason, I was honored to speak with Professor Marc Shapiro, author of the new book Renewing the Old, Sanctifying the New: The Unique Vision of Rav Kook, to learn more about Rav Kook’s ideas, and their application to the Orthodox world today. 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

Apr 28, 2025 • 1h 5min
Inside the Real Rules of War: Colonel John Spencer vs. Media Myths About Israel and Hamas (246)
Colonel John Spencer, one of the world's leading experts on urban warfare, joins me for a wide-ranging conversation about Israel’s war against Hamas. We dive deep into the realities of modern combat, the strict standards of international law, and the false accusations of "genocide" being leveled against Israel. Colonel Spencer also shares insights from his recent high-profile debate alongside Dave Smith on Piers Morgan Uncensored, where he pushed back against the misinformation dominating media narratives. We talk about the dangers of influencer-driven disinformation, the moral challenges Israel faces on the battlefield, and what the world gets wrong about the rules of war. We also discuss whether Israel is succeeding in its stated goals, and how the war can conclude without turning into an endless quagmire. No matter your stage of life, Nishmat's Summer Beit Midrash is the place for you. This program offers transformative Torah learning for women of all backgrounds, in the heart of Jerusalem. Visit nishmat.net/summer-beit-midrash to learn more. 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

Apr 21, 2025 • 1h 20min
OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
The 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. 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

Apr 7, 2025 • 1h 17min
Celebrating Pesach in Challenging Times: Haggadah Insights from Eight Teachers of Torah (245)
Join esteemed guests like Rabbi Benjamin Kelsen, who delves into the Makot and their comforting relevance during the Pesach Seder. Rabbi Dr. Judah Goldberg highlights Pesach as the holiday of Brit Avot, celebrating the ongoing covenant with God. Dr. Yosefa Fogel Wruble shares Rav Kook's insights on internal freedom and Israel's unique role. Rabbi Yitzchak Shurin explores the dual aspects of freedom in the Haggadah, and Olivia Friedman discusses themes of hunger and community. Rabbi Chayim Soloveichik reflects on the journey from agony to joy, offering profound messages for a transformative Seder.

Mar 31, 2025 • 1h 40min
"There Are No Shortcuts to a Healthy Jewish Education": Empowering Growth Without Guilt or Fear, with Rabbi Dr. Judah and Rabbanit Shayna Goldberg (244)
We are now less than two weeks away from the night of the Seder, which is almost certainly the most widely practiced example of Jewish education in action. And that raises the issue of how we should define healthy Jewish education in general, and how best we can achieve it. These questions are doubly important because while there are many wonderful Jewish schools, there are, unfortunately, numerous educational institutions where religious growth and educational goals are met through the use of fear, guilt, charismatic authority, manipulation, and condescension. Whether or not it “works” is irrelevant; education that relies on unhealthy approaches is damaging, unfair, and destructive. This episode with Rabbi Dr. Judah and Rabbanit Shayna Goldberg, explores fresh, student-centered approaches to Jewish learning that prioritize autonomy, personal meaning, and emotional well-being. We challenge guilt- and fear-based models, advocating for an education that nurtures curiosity and critical thinking, while emphasizing lifelong love of Torah, Jewish law, and Jewish tradition. How can we empower our children and students to take ownership of their learning while staying rooted in the values we want to impart? How do we create environments where kids feel both supported and free to make their own choices? We examine how Jewish education can inspire, uplift, and cultivate independent, engaged learners who embrace Torah Judaism without losing their sense of self. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit https://jcfny.org/orthodoxconundrum/ to request an information kit. 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

Mar 24, 2025 • 1h 15min
A Moral Voice for Religious Zionism: The Profound (and Profoundly Human) Thought of Rav Yehuda Amital, with Rabbi Moshe Taragin (243)
This conversation with Rabbi Moshe Taragin presents an introduction to the profound - and profoundly human - religious philosophy of Rav Yehuda Amital zt'l, the founding rosh yeshiva of Yeshivat Har Etzion. Rav Amital's ideas fill a unique niche in the Religious Zionist world today, and in many ways stand as a corrective to some of the ideology that has become dominant in the dati leumi world. His teachings grapple with some of the most pressing tensions in Jewish thought and life: universalism vs. particularism, the relationship between morality and halacha, and the relevance of Tanach as a guide to contemporary events. In this engaging discussion, Rabbi Taragin and I explore Rav Amital's vision of faith, statehood, and leadership, as well as his emphasis on joy and serenity in religious service. Rabbi Amital’s unique perspective on Zionism, ethics, and spirituality continues to inspire and challenge, offering guidance for those seeking a thoughtful and compassionate approach to Judaism and the modern world. Perhaps more than ever before, we need to hear his voice loudly and clearly so that Religious Zionism can represent the positive and diverse force that it can be, rather than the sometimes narrow and shallow force that, at times, it is in danger of becoming. Tune in as we uncover the depth and relevance of Rabbi Amital’s ideas, bringing his legacy to life for today’s listeners. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit https://jcfny.org/orthodoxconundrum/ to request an information kit. To purchase Rabbi Taragin's new book, To Be Holy but Human: Reflections Upon My Rebbe, HaRav Yehuda Amital, 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