Unscripted Reflections: Israel, Iran, and the Challenge of Faith in Wartime (251)
Release Date: 06/16/2025
When We Get It Wrong: Orthodox Communities and the Nechemya Weberman Case (279)
Orthodox Conundrum
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! This episode of Orthodox Conundrum addresses an extremely painful and unsettling subject. Last week, we learned that Nechemya Weberman, who was convicted of repeatedly sexually abusing a minor, has had his prison sentence dramatically reduced. Although Weberman originally received a sentence of more than one hundred years, that sentence has now...
info_outline
No Rewind Button: Why “It Never Happened Before” Isn’t Enough, with Rabbi Yakov Horowitz and Rabbanit Dr. Yardaena Osband (278)
Orthodox Conundrum
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! Last week in Jerusalem, two babies lost their lives. The details are painful. The families are grieving. And out of basic decency, we are not here to dissect the specifics of what happened. But moments like these force a question that is deeply uncomfortable, yet absolutely unavoidable. When tragedy strikes, especially tragedy that may have been...
info_outline
Does the Torah Demand Independent Thought? Rabbi Aryeh Klapper on Gedolim, Authority and Halacha (277)
Orthodox Conundrum
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! One of the most difficult questions in religious life is also one of the most basic: how do we show genuine respect for Torah and its teachers while still taking responsibility for our own moral and halachic decisions? At what point does kavod, or respect, become healthy reverence, and at what point does it quietly turn into something more...
info_outline
The Dating Process: An Honest Conversation for Those Dating and Their Parents, with Rabbanit Shayna Goldberg (276)
Orthodox Conundrum
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with early access and additional bonus content! One of the most common questions people ask about dating is a deceptively simple one: How do I know? How do I know whether to keep dating this person? How do I know whether this is the person I should marry? How do I know whether my doubts mean something is wrong, or whether I’m just afraid? For many people, dating becomes emotionally exhausting not...
info_outline
Turning Criminals Into Heroes: Rabbi Jeremy Wieder on Rubashkin, Pollard, and Moral Clarity (275)
Orthodox Conundrum
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with additional bonus content! There’s a recurring pattern in parts of the Orthodox world - one that has always troubled me, but in recent years has become impossible to ignore. We take individuals who have committed serious wrongdoing, sometimes admitted it in court, sometimes even served jail time, and we nevertheless elevate them to the status of heroes - not necessarily despite their criminal...
info_outline
A Person is a Subject, not an Object: New Traditional Perspectives on Tzniut, with Bracha Poliakoff and Rabbi Anthony Manning (CLASSIC EPISODE)
Orthodox Conundrum
Enjoy this classic episode from May, 2023. We'll be back next week with a brand new episode. Tzniut is triggering. That became clear when the Orthodox Conundrum Podcast released episode 145 entitled, “The Challenges of Teaching Tzniut & the Challenges of Being Tzanua, with Shayna Goldberg.” That episode, in which Scott asked Shayna to focus on issues related to tzniut (modesty) and clothing, addressed some of the most pressing concerns, and the conversation generated quite a bit of discussion. Today’s conversation is again about tzniut, this time about tzniut as a whole, and from the...
info_outline
When Non-Jews Define Judaism for Jews: Alyza Lewin on Reclaiming Jewish Peoplehood in an Age of Intimidation (274)
Orthodox Conundrum
There is a fundamental mistake that many people still make about Jews: they see Judaism exclusively as a faith, so they assume Jewish needs are basically religious accommodations, kosher food, holiday absences, maybe a space to pray. But my guest today, attorney Alyza Lewin, argues that if that’s your starting point, you completely misunderstand the nature of Judaism, and what Jews are experiencing across the world. Because what we are watching on campuses, on Bondi Beach, and in the international vilification of Israel is the vilification and targeting of Jews as a people, on the basis of...
info_outline
Jewish Particularism or Cultural Engagement: A Chanukah Debate, with Rabbi Yitzchok Adlerstein and Rabbi Dr. Raphael Zarum (273)
Orthodox Conundrum
To what degree should we assimilate non Jewish thought and culture into our intellectual, emotional, and spiritual lives? And to what degree does that question affect the way that we celebrate Chanukah? Rav Shimshon Raphael Hirsch expressed this tension directly when he wrote the following words: Chanukah represents the clash of two doctrines, two views, two civilizations, capable of molding opinions, training and educating those who until this very day compete for the mastery of the world. Hellenism and Judaism: These are the two forces whose effect upon the nations mark the historical...
info_outline
A $10,000 Bottle of Scotch: Alcohol Abuse, Conspicuous Consumption, and Orthodox Life Today, with Rabbi Jonathan Muskat and Rachel Tuchman (272)
Orthodox Conundrum
A tragic drunk driving case in Lakewood has pushed an uncomfortable question to the surface. What happens when "Toameha," kiddush clubs and casual drinking culture quietly normalize alcohol misuse in our homes and shuls, especially for the teenagers who are watching us... and what happens when that same culture is surrounded by designer logos, luxury Shabbat tables and endless talk about hotels and vacations? In this episode, I speak with Rabbi Jonathan Muskat and mental health counselor Rachel Tuchman about the growing Toameha phenomenon, problem drinking that does not always look like...
info_outline
Chosen Vs. Unchosen Vs. Rejected: The Idea of a Chosen People in an Antisemitic World, with Rabbanit Yael Leibowitz (271)
Orthodox Conundrum
In the past two years many Jews have felt as if the world they thought they knew simply disappeared. Western democracies, universities, and social justice spaces that once seemed welcoming - or at least somewhat neutral - have turned openly hostile toward Israel and the Jewish people. At the center of much of this hatred is a familiar accusation: that Jews think they are chosen, and accordingly, Jews think they are better. While we wholeheartedly reject the antisemitism implicit in this assertion, we need to honestly confront what the idea of a chosen people means, and what it says about our...
info_outlineIn this spontaneous and unfiltered episode of Orthodox Conundrum, Scott shares heartfelt reflections on Israel’s war against Iran—not from a political or military perspective, but through personal experience and the lens of faith. What does it mean to believe in Divine providence during a time of fear and uncertainty? How should we grapple with the moral and spiritual implications of war? Without a script or agenda, this episode wrestles with the difficult questions that arise when religious conviction meets the harsh realities of conflict.
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