Orthodox Conundrum

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - 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 dangerous, a way of outsourcing thought, conscience, and responsibility?
Many of us were raised with a strong emphasis on deference. Trust the rabbis. Follow the gedolim. Do not question authority. And yet at the same time, my guest today, Rabbi Aryeh Klapper, insists that Judaism does not allow a Nuremberg defense - that is, you cannot say I was only following orders. Every individual remains accountable for his or her choices.
So how do those ideas live together?
Does independent thinking strengthen Torah or threaten it? Is there such a thing as going too far in thinking for yourself? Who decides who actually has authority, and on what basis? And perhaps most provocatively, is the category of "gedolim" we frequently reference a religious reality, or merely a political one?
In this conversation, Rabbi Klapper challenges many assumptions that are often taken for granted in Orthodox discourse. He speaks about the dangers of imposed respect, the psychological cost of receiving kavod, the limits of rabbinic authority, and the responsibility that no Jew can ever fully give away, even to the greatest scholar.
This discussion was thoughtful, nuanced, and frequently surprising. It is not about tearing down Torah leadership, but about asking what real Torah responsibility actually demands from each of us.
This is a conversation about authority, respect, when it's appropriate to surrender our own judgment, and what it truly means to live as a thinking Jew within a halachic system.
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.
Write to [email protected] to learn all about creating your own podcast.
Music: "Happy Rock" by bensound.com

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - 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 because they lack options or insight, but because they believe that there must be a single, correct answer… and that getting that wrong would be catastrophic. That pressure often leads people to rush, to freeze, or to outsource responsibility to parents, rabbis, friends, or even strangers.
My guest today, Rabbanit Shayna Goldberg, offers a very different (and deeply liberating) way of thinking about dating and decision making.
Shayna is not a dating coach and not a therapist. She is a veteran educator who has spent decades teaching and listening to young adults as they navigate relationships, commitment, and uncertainty; she is also the author of What Do You Really Want? Trust and Fear in Decision Making at Life's Crossroads and in Everyday Living. What she brings to this conversation is not formulas or guarantees, but clarity.
We talk about why the hardest decisions in life are rarely between right and wrong, but between multiple possibilities. We explore how fear quietly shapes many dating choices, whether it's fear of being alone, fear of hurting someone, or fear of committing. And we focus on two core questions that matter far more than any checklist:
Do I respect this person?
And do I trust this person?
We also discuss how much weight to give chemistry, how to think about religious differences, when outside guidance helps and when it harms, and how parents can support their children without controlling their choices.
If you've ever felt stuck, pressured, or overwhelmed in dating, or if you're a parent trying to help without violating boundaries, this conversation offers wisdom, perspective, and, I believe, a welcome sense of calm.
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.
Write to [email protected] to learn all about creating your own podcast.
Music: "Happy Rock" by bensound.com

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - 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 behavior, but in some ways almost because of it.
Just a couple of weeks ago, Mishpacha magazine ran a glowing feature calling Sholom Rubashkin "the emunah and bitachon rebbe of the entire Jewish world," as though the only relevant fact of his story is his early release from prison.
But as the record makes clear, including extensive evidence presented at trial, Rubashkin was involved in significant fraud, money laundering, and the exploitation of undocumented workers. Was his sentence excessive and unfair? Absolutely. Was there government overreach? No question. But that's not the same thing as innocence, and certainly not a basis for turning someone into a moral authority.
Let me be clear: many of us have done things that we're not proud of, and that we wish we had done differently. The fact that Rubashkin went to jail is not the issue, so much as the fact that despite the real evidence, much of the Orthodox world treats him as if he were an innocent man who did nothing wrong, rather than an example of someone who was both perpetrator and victim. If he presented himself as an example of a baal teshuva, I would have no complaint. I would be pleased and fully supportive if we looked at him as someone who committed crimes, but has repented and is now living an honest life. And if he acknowledged his conviction as just and also complained about government overreach, he would be in the right. But that's not what's happening - and the consequences for the Orthodox self-image and behavior are serious.
And this is not just a Haredi phenomenon. In the Modern Orthodox world, Jonathan Pollard has long been held up as a heroic defender of Israel. But as Rabbi Jeremy Wieder points out in our conversation, Pollard betrayed the country of which he was a citizen, took large sums of money for his actions, and passed along intelligence, the scope of which none of us fully know. The fact that the U.S. government mishandled his sentencing - which is terrible - does not magically transform espionage into idealism.
So why do we do this?
Why does our community repeatedly turn criminals into role models—sometimes even into teachers of faith and morality?
What psychological, sociological, and ideological needs are we trying to satisfy?
And more importantly: what message are we sending to our children when we confuse suffering with righteousness, and denial with integrity?
In today's episode, Rabbi Jeremy Wieder helps us unpack all of this. We discuss Rubashkin, Pollard, Aryeh Deri, the role of media and influencers, the dangers of denial and victimhood narratives, and the guardrails communities should adopt so that real role models—not the loudest, or the most dramatic, or the most persecuted—become the people we admire.
It's an honest and necessary conversation about integrity, responsibility, and choosing heroes who actually reflect Torah values.
We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.
To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!
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

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 perspectives of Bracha Poliakoff and Rabbi Anthony Manning, the authors of a very well-received new book entitled, Reclaiming Dignity: A Guide to Tzniut for Men and Women. 
In this wide-ranging discussion, Scott spoke with his guests about some of the same issues discussed in the earlier podcast as well as some that are quite different. Among the topics are how to define tzniut, what has gone wrong in education for tzniut that so many people are turned off by the very word and the trauma some experience when it comes to tzniut, how to legitimize different approaches, the problem of weaponizing modesty in order to delegitimize others, how much of tzniut is subjective, the confusing of the terms tzniut and erva and the consequent problems, whether obsessing about modesty leads to oversexualization of women, the judgmentalism that seems to be part and parcel of typical thinking about tzniut, and much more.
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.
We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.
To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!
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

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 peoplehood, ancestral heritage, and our connection to the Land of Israel  - even though those who do so may not publicly acknowledge that this is their philosophy of Judaism.
And that itself is part of the problem: people who are not Jewish who think that they can decide the definition of Judaism and Jewishness. This is a process that is happening now, but its antisemitic roots go back 800 years.
That is part of why the chants and the intimidation land the way they do, and why the world's inability to even recognize the nature of the attack has left so many Jews feeling isolated.
Strangely enough, Alyza argues that despite the pain, there is a silver lining: namely, the reinvigoration of Jewish identity, and faith in God, among many of those who, until October 7th, gave very little thought to their Jewish heritage.
So in this conversation, we address a series of very practical questions, rather than dealing with antisemitism in the abstract. We ask how, in a society with broad legal protections for free speech, we should deal with the huge grey zone where speech has consequences the law may not address.
How do we distinguish good faith political debate from the vilification of Jews, especially when universities watched this for years and still misread it as a normal dialogue?
What should Jewish students do when activists demand that they shed Jewish peoplehood and connection to Israel in order to be accepted, and why does Alyza insist the answer is not to take the bait, but to say clearly: you have no right to tell me what it means to be Jewish?
Should we retire the term Zionism, or reclaim it?
And crucially, we also tackle one of the most emotionally charged pairings in today's discourse: antisemitism and Islamophobia, and how that framing often shapes, and sometimes distorts, the conversation in the public square.
Ultimately, we are dealing with reinvigoration of Jewish peoplehood. Because if we do not name Jewish peoplehood clearly, we will keep losing the argument before it even begins.
Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/.
We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity.
To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode!
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