
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

Feb 6, 2023 • 1h 10min
Disappointment, Disillusionment, and Dejection: When Rabbis Let Us Down, with Shoshanna Keats-Jaskoll (147)
One of the saddest and most poignant emotions is disappointment - that is, when your illusions are shattered, when you anticipated something great, or magical, and it doesn’t happen. Disappointment often means that a piece of innocence is irretrievably lost. What do we do when people we believe in, people we look up to as paragons of virtue, disappoint us? What happens to our faith when great rabbis in whom we trusted actually, like Hans Christian Andersen's emperor, have no clothes? Join Scott as he talks about disappointment and faith, particularly with regard to trust in Gedolei Torah, with Chochmat Nashim founder Shoshanna Keats-Jaskoll. 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

Jan 30, 2023 • 1h 18min
Rav Moshe Kahn ZT"L and the Future of Women's Torah Study (146)
On January 18th, Rabbi Moshe Kahn passed away at the age of 71. The tributes to him as an ideal teacher, talmid chacham, and rebbe immediately started pouring in across social media. As one of today’s guests asserted, if a woman wanted to engage in serious Talmud study in New York for the past four decades, Rav Kahn was the address. The obvious love and dedication shown towards him by his students from Stern and Drisha made it clear that he was someone whom we all should know more about, and continue to learn from after his passing. Four close students of Rabbi Moshe Kahn’s - Rabbanit Anne Gordon, Rabbanit Sally Mayer, Dr. Shana Strauch Schick, and Rabbanit Rachel Weber Leshaw - joined Scott on the podcast to talk about his life, his legacy, and what he meant to each of them. They discussed his derech halimud - that is, the methodology he utilized when he learned and taught Torah, whether he saw himself as a revolutionary in teaching generations of women, why it seems that many members of the Orthodox community know very little about him, as well as broader topics such as the future of women’s learning, whether there should be a unique methodology in Torah learning for women that is distinct from men’s derech halimud, and much more. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook. Check out the Orthodox Conundrum YouTube Channel. 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

Jan 23, 2023 • 1h 36min
The Challenges of Teaching Tzniut & the Challenges of Being Tzanua, with Shayna Goldberg (145)
Tzniut, or modesty, is one of the most controversial issues in the Orthodox world today. Indeed, different people see the issue of modesty through different lenses. Some wonder about how to teach students and children about tzniut so that they’ll be more inclined to follow the halachot and established Orthodox customs; others ask questions from the opposite vantage point, wondering about whether tzniut is an inherently oppressive system that leads to an unhealthy body image, increases a sense of counterproductive shame, and completely ignores the need for self-expression. Some people look at tzniut as representative of a woman's role in Judaism, and others see that attitude as an unhealthy and repressive obsession. With this in mind, Scott invited Shayna Goldberg to have a difficult but necessary conversation about the challenges that surround the issue of tzniut. The topics they discuss include whether we need to redouble our efforts to emphasize that tzniut applies to men as well as to women; why it seems that many women find tzniut more challenging and repressive than other aspects of Torah Judaism; what is a healthy way to teach tzniut without turning it into an obsession; to what degree societal factors influence our perception of what is considered modest behavior; the difficulty in that women are told to downplay their sexuality, whereas this very requirement itself sexualizes them; the fact that the laws of tzniut that women are told to follow were codified by men; whether following tzniut undermines self-expression; the reality that we often use the yardstick of modesty to declare whether someone is religious; and more. To visit the Deracheha website, go to https://www.deracheha.org/. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook. Visit the Orthodox Conundrum YouTube Channel to watch the video of this podcast. 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

Jan 16, 2023 • 55min
LGBTQ+, Jewish Law, and Compassion, with Rav Yoni Rosensweig (144)
One of the most difficult issues confronting the Orthodox world today is the question of how to welcome people who identify as LGBTQ+, while simultaneously affirming the Biblical injunction that forbids sex between two men, and the Rabbinic prohibition that forbids sex between two women. This initial question opens up a host of additional challenges, including: how do we explain a mitzvah that appears to many people to be immoral? Can we be welcoming to gay couples without undermining the Torah value that encourages the building of a family with both a mother and a father? Does Torah thought and law accept the idea of defining people based on their sexual preference? Can a gay couple adopt according to Jewish law? Should Jewish law make room for some form of gay marriage? Does it make sense for religious Jews to support pride parades? If we are going to be welcoming, does this include allowing men who identify as gay to lead the synagogue services? How can we understand a mitzvah in the Torah that seemingly commands that people permanently repress their basic sexual drives? On this episode of the Orthodox Conundrum, Scott discussed these and other questions with Rav Yoni Rosensweig. Rav Yoni has a voice that carries tremendous religious weight, as he demonstrates deep, unapologetic, and uncompromising commitment to Torah and Jewish law, while concurrently displaying real compassion and understanding of the challenges that many people face. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook. Check out this conversation on the Orthodox Conundrum YouTube channel. 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

Jan 9, 2023 • 56min
Jewish-Muslim Dialogue: Serious Challenges and Unique Opportunities, With Rabbi Dr. Yakov Nagen (143)
Just over a month ago, the Orthodox Conundrum released an episode of this podcast entitled, Confrontation 2022: Jewish-Christian Dialogue and Its Questions, with Rabbi Pesach Wolicki. Pesach discussed why he believes that his work has value, what kind of pushback he’s received, whether he’s providing an opening for missionary activity, how he justifies speaking in churches, and more. Today’s episode is, in some ways, a follow-up to that episode. Rabbi Dr. Yakov Nagen is one of the leading advocates of Jewish-Muslim dialogue - a discipline which offers great opportunities, at the same time that it creates new questions and serious challenges. In this conversation, Scott asked him about how he talks to Muslims about Israel, whether he avoids the question of sovereignty over the Holy Land, Jerusalem, and the Temple Mount altogether or whether he’s willing to confront it with them head on, if this dialogue is truly mutual, to what degree large Islamic terrorist organizations like ISIS, al Qaeda, and Hezbollah are representative of the wider Muslim population, how he answers Muslim misconceptions about Jews, what he hopes to achieve, and much more. Given the political reality in which Israel finds itself, the success of Rabbi Nagen’s work is potentially of vital importance for the future of the entire Middle East. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook. 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 Photograph credit: Dida Mulder

Jan 2, 2023 • 55min
Does Modern Orthodoxy's Attitude Toward LGBTQ+ Represent A Moral Failure? Responding to Ben Shapiro (142)
On December 12th, well-known political commentator Ben Shapiro published an article in the Jewish Press entitled "Modern Orthodoxy’s Moral Failure." Its opening paragraph reads, “Modern Orthodoxy is in a state of crisis. It is in a state of crisis because its leadership has, in large measure, abandoned its central principles in favor of political expedience, surrendering long-term interests for short-term tactical maneuvering.” While it's unfair to summarize a reasonably long article in just a few words, Ben Shapiro focuses on what he sees as the weak-kneed response of numerous Modern Orthodox institutions to the challenges posed by secular morality - and, in particular, the acceptance of LGBTQ+ identities as inherent and definitional. He writes, “The conflict between Jewish identity – rooted in halachic observance, a belief in the morality of the Torah, and a deep-seated sense of free will – and the secular worldview has reached its apex with the rise of the LGBTQ+ movement. That movement reduces identity to sexual desire – the most powerful feeling human beings supposedly have – and then demands that society’s institutions celebrate all of its claimed identities. The movement goes even further, demanding that society’s institutions celebrate identities that run directly counter to biological fact by giving credence to men identifying as women, and the like.” Shapiro’s article garnered significant comment in the Orthodox world, and many have wondered if his characterization of Modern Orthodoxy, as well as Orthodoxy’s response to the challenges he outlines, misses the mark. Rabbi Dr. Tzvi Sinensky, who wrote a response that was published in the Jewish Press on December 21, spoke with Scott about the points with which he takes issue in Ben Shapiro’s article, where he thinks that Shapiro is correct, and what practical steps are necessary to move forward from 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). 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

Dec 26, 2022 • 1h
Different Roles, Different Relationships, & Different Skills: Rabbinic Counseling and Psychotherapy with Rabbi Larry Rothwachs (141)
This podcast has frequently alluded to the problems that arise when rabbis mistakenly don’t stay in their own lane, and end up advising people in areas that require more than the pastoral counseling they might have learned when studying for semicha. Indeed, there is reason to be concerned about the intersection between rabbinic counseling and psychotherapy, and how the professional - and the congregant or client - knows which is required in any given situation. And the answers are not always so clear cut. For that reason, Scott was honored to speak to Rabbi Larry Rothwachs, a well-regarded congregational rabbi, a licensed social worker, and the Director of Professional Rabbinics at RIETS at Yeshiva University to discuss many of the issues that arise from this potential conflict, including what mental health issues are most prevalent in the Orthodox world, the specific differences between rabbinic counseling and therapy, how to navigate conflicts that arise between a person’s role as a rabbi and a therapist, the problems that result from rabbis and therapists getting involved in areas in which they are not trained, how a person should know when what is being discussed is “above his pay grade,” what a therapist committed to Jewish law should do when a therapist’s response to a problem may differ from what halacha would prescribe, and more. Listen to Praying On Purpose - short motivational messages and Torah insights by Rabbi Larry Rothwachs. Delivered 3x a week, these messages are crafted to inspire increased thought and enhanced awareness of the prayers that we recite, focusing on the “why,” the “how” and the “what” of daily prayer. 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

Dec 19, 2022 • 1h 4min
The REAL History of Chanukah... And Why It Matters Today, with Dr. Malka Simkovich (140)
Something about Chanukah speaks to almost all of us... which highlights the fact that the message of Chanukah retains enough ambiguity that different groups can understand it in different and even contradictory ways. This ambiguity goes back to the very earliest days of the holiday’s celebration while the Second Temple still stood; it’s reflected in Rabbinic sources and in our liturgy, as well. And that, in turn, leads to a number of fascinating questions about what Chanukah is really about, when we look at it through an historical lens. Chazal famously ask, "Mai Chanukah" - "What is Chanukah?" - and that question still needs to be answered today. Scott welcomes Dr. Malka Simkovich to the podcast in order to address that question, and to hear her fascinating insights about what happened before, during, and after the Maccabean revolt. Dr. Simkovich discusses the story of Chanukah, whether our sources for the Chanukah story should be considered historical (and the associated question of what history meant to people living 2000 years ago), the discrepancies between the story as presented in Masechet Shabbat and in I and II Maccabees, the false binary of emphasizing the miracle of the oil versus the military victory, how early Christians saw the Hasmoneans as Christian martyrs and whether Al HaNisim was written partially in response to that appropriation, why Chazal developed an ambivalent attitude toward the Hasmonean dynasty, what historical event in 63 BCE is widely ignored but changed the course of Jewish history, the different ways that Jews in Israel and in the diaspora understood Chanukah, the concept of “Common Judaism,” what mistaken message do too many people derive from Chanukah, and more. And along the way, Dr. Simkovich also offers some tantalizing ideas about whether our sacred texts are actually describing history as we understand it - and why a more relaxed attitude toward that question might be helpful for all Orthodox Jews today. 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

Dec 12, 2022 • 1h 9min
Rabbi Jonathan Sacks ZT"L (Part 2): His Thought and Philosophy (139)
On November 14th, the Orthodox Conundrum released a panel discussion dealing with Rav Jonathan Sacks zt’l’s life, leadership, and legacy. Today we offer a sequel to that episode, as Scott speaks with Dr. Tanya White and Rabbi Dr. Samuel Lebens about the thought and philosophy of Rabbi Sacks. They address many important issues, including Rabbi Sacks’s originality, his idea of covenant, the importance of individual responsibility, for whom he was writing, the controversy around his book The Dignity of Difference and whether he clarified or retracted its most controversial assertion, how communitarianism affected this thinking, his response to fundamentalism, whether he was a religious pluralist, how he dealt with Biblical criticism, what to do when our sense of morality and our understanding of science seem to contradict ideas in the Torah, 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). 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 Photo by cooperniall, CC BY 2.0 , via Wikimedia Commons

Dec 6, 2022 • 1h 28min
Confrontation 2022: Jewish-Christian Dialogue and Its Questions, with Rabbi Pesach Wolicki (138)
Scott and his close friend Rabbi Pesach Wolicki founded a yeshiva, Yesodei HaTorah, over 18 years ago. Yesodei HaTorah was dedicated to skill building in reading Jewish texts, and helping each student develop an independent Torah philosophy. And in 2015, the yeshiva closed down when it didn’t recruit enough students to keep it going. At that point, Scott moved into the podcasting sphere. Pesach, in turn, became deeply involved in Jewish-Christian dialogue. Now, seven and a half years later, Pesach probably spends more of his working day talking to Christians than to Jews - even though he lives in Israel. His career move can perhaps be seen as radical, maybe even unique. Why does he think this work is important? What is some of the pushback that he’s received, and how does he answer his colleagues’ objections? Is he providing a bridge that helps Chrisitians missionize Jews? What does he say about Rav Soloveitchik’s prohibiting the very dialogue that he is involved in every day? Is he violating Jewish law by speaking in churches - something he does regularly? And, perhaps most crucially, what does he hope to achieve through his work? Listen to the conversation and see whether you agree. 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