The Dating Process: An Honest Conversation for Those Dating and Their Parents, with Rabbanit Shayna Goldberg (276)
Release Date: 01/12/2026
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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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_outlineCheck 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).
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