
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

Oct 30, 2023 • 46min
While Israel Slept: Questions, Puzzles, Issues, and Options Related to the War in Gaza, with Yaakov Katz (180)
There are so many questions about where the State of Israel is heading after this war, and so many puzzles about how we ended up in such a precarious position in the first place. We are rightly proud of the sense of unity that we are currently experiencing; but we cannot let it blind us to the reality that things have to change in the future in order to make sure that Israel is not again lulled into a false sense of security. In this episode, Scott spoke with Yaakov Katz, senior fellow at the Jewish People Policy Institute and a former editor of the Jerusalem Post. Among the important topics that they addressed are what failures led to the massacre on October 7th, what was Hamas’s expectation at the time, whether the protests around judicial reform contributed to the security failures, why it has taken so long for a ground invasion to begin, when to believe the government and when to wonder if they are intentionally trying to mislead Hamas, Hezbollah, and Iran, why so many in the government have been strangely quiet for the past three weeks, what the current crisis has in common with the tragedy in Meron two and a half years ago, what may happen with Israel’s political system when the war is over, why this may present a unique opportunity for change, and 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Oct 23, 2023 • 1h 1min
G-d Wants Us to Fight Evil: Thinking About the War Through the Lens of Jewish Law and Thought, with Rav Yoni Rosensweig (179)
Israel's war against Hamas has brought the Jewish people together in ways many of us have never before experienced. It also has brought new halachic and hashkafic challenges to light that, as religious Jews, we are obligated to address. In this episode, Scott spoke to Rav Yoni Rosensweig about some of these challenges, including the right and wrong way to engage in self-reflection, what sorts of actions we can all be doing now in order to help the war effort and ourselves, the ways that we should face the fact that this seems like a time of hester panim, of G-d’s hiding His face, and how we should face our fears in a healthy and Jewish way. Rav Yoni also discussed numerous halachic queries, including questions regarding using phones on Shabbat, the idea of a soldier writing a document to avoid his wife's (G-d forbid) becoming an aguna, the kashrut of food sent to the front from unknown sources, and 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. Click here to listen to Dr. Matthew Levitt's excellent podcast, Breaking Hezbollah's Golden Rule. 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

Oct 17, 2023 • 25min
I'm So Proud of the Jewish People, and Other Thoughts: Living Life While Israel is at War (BONUS EPISODE)
After ten days of war in Israel, Scott talks about the Jewish People, the Divine Presence, people who are emulating the wicked son from the Pesach Seder, why Jews Who Matter need to read the Book of Esther, meaningful support from wonderful people who are not Jewish, and more. It might be disorganized, and it might seem random... but maybe that's the most honest kind of podcast after the events of the past week. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Oct 12, 2023 • 42min
The Catastrophic Success of Hamas, and Israel's Massive Response: A Deeper Look at Israel's War Against Hamas, with Dr. Matthew Levitt (178)
There are so many questions, and people want to know what's actually happening. In this special rush-released episode of the Orthodox Conundrum, Scott speaks with Dr. Matthew Levitt about Israel's war against Hamas. Among the issues they discuss are why Hamas decided to commit these atrocities now, what Hamas expected to occur and what actually took place, whether Hamas anticipated Israel's full response, the possibility of a multi-front war, if Jews should be concerned about Khaled Mashal's call for Muslims to demonstrate across the world on October 13th, whether it's possible to fully eliminate Hamas, and 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). Read Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Oct 9, 2023 • 48min
There Was Before... And Now There's After: Reflections on the War in Israel with Talli Rosenbaum and David Lange (177)
Talli Rosenbaum and David Lange discuss the emotional distress caused by the war in Israel and media portrayal. They explore coping strategies and supporting others during times of trauma, including talking to children and supporting friends. They also touch on international reactions and biased media coverage. Visit the website for more information on media reactions to Israel.

Sep 26, 2023 • 1h 7min
"A Theology of Distraction": Exploring the Conundrums of Kohelet with Dr. Erica Brown (176)
Megilat Kohelet is one of the most difficult books in Tanach: it jumps back and forth between conflicting assumptions, it lacks any obvious narrative or thematic structure, and its statements sometimes seem at odds with what most people would consider standard Rabbinic theology. People didn’t discover these problems today, of course; the Mishnah in Masechet Yadayim questions whether Kohelet was canonized as part of the Bible or not. Moreover, Masechet Shabbat 30b reports in the name of Rav that the Sages wanted to hide Kohelet because of its contradictions; they decided against it because its beginning and end are words of Torah - and as Rashi explains, that means that surely there must be other words of Torah in the middle. Still, the fact that they even considered this tells us that Kohelet was as mysterious to them as it is to us. We read Kohelet on Shabbat chol hamoed of Sukkot - or, in a year like this where there is no Shabbat during chol hamoed, on the first day of Sukkot in Israel, or on Shmini Atzeret outside of Israel. But going through all twelve chapters quickly in shul is not the best way to internalize the many messages of this intriguing book. For that reason, Scott was extremely gratified to welcome Dr. Erica Brown back to the podcast. Erica is the author of Kohelet and the Search for Meaning, and they discussed some of the many questions that are raised by Kohelet. It’s a wide ranging and fascinating conversation that invokes Shlomo HaMelech, the Byrds, C.S. Lewis, William Blake, George Carlin, Sesame Street, and more. It will give you a new appreciation for Kohelet not only as a sacred text, but as a book that speaks directly to the deepest concerns of human beings living in the 21st century. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Sep 18, 2023 • 1h 8min
Guilt and Shame, Repentance and Redemption: A Deeper Dive into Teshuva with Elisheva Liss (175)
The ten days between Rosh Hashanah and Yom Kippur are dedicated to teshuva, commonly translated as “repentance” or “return.” According to the Rambam’s classic formulation, repentance consists of three elements: regret, determination not to repeat the sin in the future, and confession. In many ways it sounds relatively simple… though in practice, it’s often much more difficult. Moreover, from a psychological perspective, the processes of repenting, apologizing, and forgiving are very complex. What does it mean to experience shame, and how is the regret required by Jewish law different from the paralyzing shame that psychologists discourage? Can someone truly experience shame when that person still reaps the benefits of his wrongdoing? Is apologizing to someone different from asking for forgiveness - and what, exactly, is forgiveness, anyway? Are there techniques that can make it easier for us to forgive those who have hurt us? Is it ever wrong to apologize? And what if someone is convinced that he or she is simply unredeemable? In order to discuss these issues from both religious and psychological perspectives, Scott spoke with marriage and family therapist Elisheva Liss on the podcast. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Sep 11, 2023 • 1h 3min
"It's About Holding People in their Pain": Infertility and the Orthodox Community, with Dr. Aimee Baron (174)
Rosh Hashanah is a day of judgment, but it also represents renewal, hope, confidence, and optimism as we look toward the future. This is expressed in many ways, but perhaps most obviously in the Torah reading of the first day of Rosh Hashanah, where we read that Sarah, after a lifetime of being unable to have children, gave birth to Yitzchak at the age of ninety. In the haftarah of that same day, we read the similar story of Chanah, who was barren until G-d accepted her prayer; she gave birth to Shmuel HaNavi soon thereafter. But these stories of hope, alongside other themes of Rosh Hashanah, may have the opposite effect for people who suffer from infertility. Seeing families in the synagogue, sitting around a yom tov table alongside couples who have children, and even hearing that G-d answered Sarah yet wondering, “Why hasn’t He said yes to me, too?” - may be exceedingly painful. To discuss some of the issues of infertility, including how we all can develop the proper sensitivity to those who suffer from infertility, Scott was honored to speak with Dr. Aimee Baron, the founder and executive director of I Was Supposed to Have a Baby. Read "59 Things to Talk About Other Than Babies and Kids" here. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. If you subscribe by Thursday, September 14, you will receive a free PDF of The Laws of Tekiat Shofar. 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

Sep 6, 2023 • 29min
When God Says No: A Pre-Selichot Conversation with Rebecca Sarchi (Special Episode)
The tefilot of the Yamim Nora’im - starting from Selichot and continuing through Rosh Hashanah and Yom Kippur - are deep and meaningful, but also long and often quite hard to understand. But that difficulty is minor compared with the theological problem of how to relate to God when our prayers go unanswered... when He seems to have abandoned us... when rather than a divine nod of approval, we feel like we are getting God’s cold shoulder. This is a topic which Scott discussed over the past two weeks in his Substack, Orthodox Conundrum Commentary; it’s also an issue that everyone must confront at one point or another. To that end, Scott spoke with Rebecca Sarchi, a high school principal living in Johannesburg. Right before Tisha B’Av, her son Chaim tragically passed away; despite their intense tefilot and mitzvah observance, God still said no. Rebecca decided that she wants to address what happened, and describe the ways that a person can maintain faith in the face of unthinkable tragedy. She does not provide answers; instead, she simply talks about her and her family’s experience. She mentions the importance of prayer despite the possibility of God’s saying no. She describes the need to cherish every moment, and to live fully in every second. She advocates going outside of yourself, and reaching out to someone else. No, none of these are answers; instead, they are lessons that can hopefully help us gain proper perspective as we enter the end of Elul, and begin the countdown to Rosh Hashanah and Yom Kippur. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

Aug 28, 2023 • 1h 14min
"I Didn't Know There Could Be a Bad Rabbi": Confronting Emotional and Religious Abuse, with Rabbi Mark Dratch and Mrs. Rachel Dratch (173)
What may a teacher or kiruv professional do in order to make people frum? Do the ends of bringing people closer to Torah justify the means of manipulating them emotionally? And even if the methodology is valid in some way, does it even work? According to Scott, playing mind games in the service of religion is not just wrong, but literally abusive. It potentially causes trauma, and further cements, in both the teacher and the students, the damaging idea that the teacher has special access to spiritual truth that is denied to the student. While someone who has studied Torah hopefully has a greater knowledge of Jewish law, and while he or she may potentially possess insights into spirituality, that does not translate into genuine knowledge of the mind of G-d; in reality, those who abuse often seem to profess shallow inanities that desecrate G-d's name. Yet some abusive rabbis have become famous and popular not despite their hurtful words, but because of them. And there are others - less famous, to be sure - who may be teaching in the schools attended by our children. To learn more about this troubling phenomenon, Scott spoke with Rabbi Mark Dratch and Mrs. Rachel Dratch. 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). Check out the Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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