edJEWcation

In honor of Yom Kippur, we talk about two kinds of sins we commit. Sins of omissionand sins of commission. Sins of omission are the things we should have done and didn’t, and almost nobody puts those on their list of things to repent for because, well, we may not have known we committed them. Sins of commission are the things we were aware did: the thing we said, the thing we took, the person we hurt. In this episode, we get into: Sins of omission: the Noda B’Yehuda, the widow at the edge of town, Bilaam’s “I have sinned, for I did not know,” and John Wooden coaching only the mistakes his players didn’t notice Sins of commission: why we ask forgiveness for traits God gave us, and the filter of Daat that is supposed to run passion, anger, and speech (a 25-year friendship can be destroyed in two minutes of talking) Whether your community owes you a correction, why nobody in America wants to give one, and the art of the well-timed apology (do not bring the flowers on Friday afternoon) Hannah, the mother of Samuel, what it means to pray “on” God instead of “to” Him, and why hope is not a plan Avinu Malkeinu: whether we want God as a king or a father, praying for money, and what fear does to free will Shifra and Puah, the Righteous Among the Nations, “please don’t test me,” and why Teshuva means return, not repentance If you are heading into Yom Kippur with a list of things you did wrong, this episode might convince you to add a second list: the things you didn’t do at all. Listen before the fast, and may we all be sealed for a good year Past Yom Kippur episode

Jay has been doing some reading, and he opens this week with an essay he refuses to attribute until the Rabbi guesses. From there the Rabbi gets on a roll about Mark Ruffalo, Javier Bardem, and Hasan Piker (he calls him something else), and why the four in ten Jewish college students pulling back from Jewish life are a bigger threat than any of them. Then we hit the holidays, because Rosh Hashanah 5787 is a week away and ChayaLeah brought questions. In this episode, we get into: Jabotinsky’s “No Apologies” and why we should stop defending ourselves to people who already wrote the verdict When to fight antisemitism and when to let the buffalo be a buffalo Ben Shapiro’s “as Jewish as a ham sandwich” line, why the rabbis were right that he doesn’t get to decide, and why ChayaLeah thinks Bernie Sanders belongs in a category of his own Amalek, the first nation to attack us after Egypt, and the people who give everyone else cover How to walk into shul on Rosh Hashanah when you don’t know Hebrew, the tunes, or anyone in the room Whether parents should guilt their adult kids into coming home for the holidays (the Rabbi has a phone call script, and it involves a fake divorce) What to say to a young adult with no hope, no friends, and twelve hours a day of video games, from Elie Wiesel to Pirkei Avot to a Talmudic line about prisoners Why nobody is inviting the single mom or the divorced friend for Shabbat, and what to do about it Shanah Tovah from all three of us. Come sit with us for an hour, nobody is checking whether you know when to stand. Subscribe now Share Leave a comment

Jonah gets swallowed by a fish, and that is the part everybody remembers, but the real story is what happens after: Nineveh repents, Hashem forgives, and Jonah sits down under a plant and sulks about it. In this episode, we get into: The kikayon, the plant that grows over Jonah and dies overnight, and the question God closes the book with about 120,000 people Why justice and mercy are not opposites, and why the Rabbi says everyone alive needs some measure of both How a tzaddik does teshuvah when he has not sinned, and what unreached potential has to do with it A murder trial in the news right now, the insanity defense, and the Talmud’s category of a shoteh Whether the right answer for someone who is already suffering is prison, execution, or therapy Jonah the seer, who knew Nineveh would come back for us, and what that has to do with Israel and Yahya Sinwar Why the Yom Kippur Mincha haftarah sells for thousands of dollars, and why you should stay in shul for it If you usually go home after Musaf and come back for Neilah, this is the year to stick around for Mincha. Come sit with the hardest question in the machzor with us.

Some weeks we pick the topics. This week you picked them for us. The Rabbi opens by informing both of us that the frivolity is over, because Elul has arrived and we have thirty days to get our act together before Rosh Hashanah. Also, he would like an apology for being cut out of last week’s episode (an apology is not forthcoming). Then ChayaLeah tells us about a 6 am Uber ride in Jackson Hole that she was too tired to want, with a driver who would not stop talking about Hashem, trees, and energy, and who turned out to be saying exactly the thing she needed to hear. And then we open the mailbag. In this episode, we get into: Why Elul works like a thirty day notice before the tax bill, what gets added to the prayers, and why teshuvah is a terrible translation of “repentance” The year Rosh Hashanah falls on Shabbat, no shofar on day one, and the headline about 9/11, COVID, and October 7th that nobody needed to see right now The five categories of damages in Torah law, and how a family divides one lump sum among kids who were all in the car but not all hurt the same Whether settlement money is blood money, from an insurance check in America to the fight in 1950s Israel over taking German marks Where you actually start if you want to engage more with Judaism, why Judaism is a religion of deeds before creeds, and why you will never understand kosher before you keep it What to say when a friend, a cousin, or a sibling drops “genocide” at dinner, who is worth engaging, and when to just walk away You ask, we answer, whether or not we know what we are talking about. Send us your questions and we will do this again.

It is just CL and I this week, because we wanted to give her a chance to speak this week (sorry, Rabbi). Her oldest son got engaged a few weeks ago, there has already been an engagement party in Crown Heights and a second one on the West Coast, and the wedding is coming fast. So we thought people would be interested: what actually goes into planning a Chabad Hasidic wedding? The answer starts with a phone call where you plan a huge party with people you have never met, and it only gets more interesting from there. In this episode, we get into: Why dating stays a secret until the engagement is announced at the Rebbe’s grave, and why the whole thing takes weeks instead of years Who pays for what, the fifty fifty split, and the gifts each side is expected to give Takana weddings, the thirty thousand dollar all in package that makes sure every couple gets a beautiful wedding, and why the community treats that as everyone’s responsibility The seven days before the wedding when the bride and groom do not see or speak to each other, get escorted everywhere, and get treated like a king and a queen Fasting on your wedding day, why it is considered a mini Yom Kippur, and the Rosh Chodesh loophole The badeken, the completely opaque veil, and the moment the next morning when the bride covers her hair for the first time Sheva Brachos, a full week of parties, and why the wedding is really a celebration of the entire family Come for the logistics, stay for ChayaLeah whispering under her own chuppah asking if anyone was even out there.

Moses has five weeks left. He starts talking on the first of Shevat, he dies on the seventh of Adar, and in between he delivers the longest, most repetitive, most urgent speech in the Torah. The traditional name for it is Mishneh Torah, the repetition of the Torah, and many commentators say this is the one book Moses spoke on his own behalf. So this week we skip the parsha by parsha treatment and take the whole book at once, because the themes only show up when you stand back far enough to see them. In this episode, we get into: Why Deuteronomy reads differently from the first four books, and what “Moses spoke on his own behalf” actually means The discrepancies with Numbers, starting with who really wanted to send the spies, plus the small differences in the Ten Commandments Who Moses is actually talking to: a generation born in the desert with no slave mentality and no memory of Egypt The warning that prosperity, not persecution, is what makes people forget, and how uncomfortably well that lands in America Why Moses was not allowed to enter, what God showed him from the mountain, and why he wanted in so badly in the first place The Shema line by line: hearing as integrating, why “one” and not “alone,” the two inclinations hiding in V’ahavta, and how anyone can be commanded to love We also end up on free will, the chocolate bar, and a sixth grade yearbook from 1992 that somehow ties the whole thing together.

Nobody warns you that the hardest parenting years might come after your kids are grown. We opened with a story Jay picked up in a Delta Lounge, a man quietly putting on tefillin who turned out to be a Soviet Jew that did not learn he was Jewish until his family reached America. That pulled us into the Rebbe and Soviet Jewry, quiet diplomacy versus loud demonstrations, and a father exiled to Kazakhstan whose wife made ink from berries so his Torah could survive. Then we turned to the question a lot of you have written in about: how do we stay parents to our kids once they are adults with lives, spouses, and kids of their own? In this episode, we get into: Why grown children still need their parents more than anyone expects, and what that means for us Where the boundary sits, and how to give feedback that lands from a place of love instead of criticism Protecting your spouse first, and why in-laws have to tread more carefully than parents Raising kids who become friendly with you without ever forgetting you are the parent Free choice, and how you can do everything right and still get a result you did not plan for Overbearing parents, helicopter moms, the Little League dad, and when to bring in a third party Whether you are the parent watching your kid make a call you would not make, or the adult child trying to keep the peace, come sit with us. There is grace in here for both sides.

Tisha B’Av is coming, and before we sit on the floor with the lights low, we’re doing our homework. This week we open the Book of Lamentations, the scroll Jeremiah wrote as Jerusalem fell (or was about to fall, depending on which commentators you ask). It’s a book with a wild backstory: a king who burned the first draft, a scribe named Baruch who took dictation for round two, and an alphabet-shaped message hiding in the book. In this episode, we get into: Who Jeremiah was and why nobody wanted to hear his “doom and gloom” prophecies The scroll King Yehoyakim burned, and what Rashi says was in it Was Lamentations written before the destruction as prophecy, or after as eyewitness testimony? Why Jerusalem is described as a widow, and what that metaphor really means The Dubner Maggid’s parable of the needle-and-thread wagon: trading something real for nothing Whether Jews blame themselves too much for their own tragedies, from the Babylonians to October 7th Why we end our reading of Lamentation not on despair but on “bring us back to You, Hashem, and we shall return” It’s the heaviest book in Tanakh, but we promise this isn’t a stuffy seminary lecture. Come study with us before the fast.

The Rabbi opens with a request: can we please put a moratorium on the word “anti-Semitism” until next July 4th? (Spoiler: no, but we try.) Then we celebrate some family news and dive into Matot-Masei, the double portion that closes out the book of Numbers. The Rabbi calls it one of the juiciest parshas of the year, and he makes his case: a war, an angry Moses, a real estate negotiation gone sideways, and an ancient legal system for accidental killers. In this episode, we get into: Why some Torah portions are read as doubles, and who divided (and named) the parshas in the first place The trup (cantillation): how an ancient melody quietly narrates the story, including Joseph’s famous pause with Potiphar’s wife Gad and Reuben asking to stay east of the Jordan, and how one reversed word order exposed their priorities What the tribes’ obligation to fight alongside their brothers says about diaspora Jews when Israel is at war Cities of refuge: the Torah’s “safe space” for accidental killers, and why the tribe of Simon got scattered on purpose Whether you grew up with this parsha or you’re hearing “Matot-Masei” for the first time, pull up a chair. There’s a waffle bar story in here too. Links Parashat Matot-Masei (Numbers 30–36) Gad and Reuben’s request and Moses’ response (Numbers 32) “Every shock fighter among you crosses the Jordan” (Numbers 32:20–24) Cities of refuge (Numbers 35:9–34) The shalshelet in the Joseph and Potiphar’s wife story (Genesis 39:8) Shogeg vs. ones, laws of exile “Kol Yisrael arevim zeh bazeh” (all Jews are responsible for one another) “Those who tend a tree eat the fruit” (Proverbs 27:18)

Some episodes start light. This one starts with a candle. We begin with Jay’s yahrzeit for his mom, twelve years gone and still deeply missed, and the Rabbi walks us through what the anniversary of a death really means in Jewish tradition. From there we widen out to a fast day heavy with history and a piece of tech that might change how any of us learns Torah. In this episode, we get into: What yahrzeit means and why we say Kaddish for eleven months, then every year after The Rabbi’s own story of counting down the days, and the strange sadness when Kaddish ends The five tragedies of the 17th of Tammuz and the start of the Three Weeks Why you can get engaged during the Three Weeks but not married (and what that says about free will) Yochai, the new AI tool that turns anyone into a Torah study partner

What makes two rabbis who disagreed about almost everything the most celebrated pair in Jewish history? This week we sit down with Hillel and Shammai, the original dynamic duo, and the answer turns out to be the way they argued, not what they argued about. In this episode, we get into: The lost art of disagreeing with someone you actually like and respect, and why Judaism treats a good argument as something close to sacred. Machloket l’shem shamayim: what makes an argument “for the sake of heaven,” and where the line gets crossed The Hanukkah menorah debate: do you start with eight candles or one, and why each side is right The gentile who asked to learn the whole Torah on one foot, and the very different answers Hillel and Shammai gave Why Hillel’s golden rule (”what you don’t want done to you, don’t do to others”) is not the same as “love your neighbor as yourself” Lenient versus strict: how two yeshivas, two personalities, and one open door shaped Jewish law Why we almost always rule like Hillel, and the surprising reason it comes down to humility Pull up a chair, pick a side, and remember: the rest is commentary. Resources: Hillel and Shammai, sayings and character Machloket l’shem shamayim (a dispute for the sake of heaven) Korach’s rebellion against Moses and Aaron

We made it to the finish line. After two earlier episodes, we wrap up the Twelve Prophets and tie a bow on them all. Along the way we get into why these texts barely show up in yeshiva, a much-debated Midrash about Adam and the animals, and whether religion or just plain ideology has driven the worst of human history. Then we go prophet by prophet, all the way to the very last words of prophecy. In this episode, we get into: Micah, and the “swords into plowshares” verse that 99 percent of the world wrongly credits to Isaiah Nahum and the fall of Nineveh, plus a thorny question: if God wanted the exile, why blame Assyria for carrying it out? Habakkuk, who opens by arguing with God and reduces all 613 commandments to one: the righteous shall live by his faith Zephaniah on fear, fight-or-flight, and the command “do not fear” Haggai, Zechariah’s colored-horse visions, and Malachi closing the prophets with the hearts of parents and children turning back to each other Grab a book of the prophets and read along with us. It only takes a few minutes a day, and as we say in here, it’s no great honor to be ignorant. Resources: Micah Nahum Habakkuk Zephaniah Haggai Malachi

We picked up where we left off with the Twelve Prophets (Trei Asar), and Hosea throws us straight into one of the strangest stories in all of the Tanakh. Gd is furious that the Jewish people are chasing idols, so He gives Hosea an unusual assignment: go marry a woman of ill repute, have kids with her, and name them “Not My People” and “No Mercy.” It’s harsh, it’s strange, and the Rabbi calls it the most dramatic living metaphor any prophet was ever asked to act out. In this episode, we get into: Hosea, the harlot metaphor, and the Kabbalistic question of whether Gd can actually be affected by what we do What a prophet (and a leader) is supposed to be: tough on the people, defender to Gd, never a politician Joel and the locusts, the seven-year famine, and when punishment came measure-for-measure Famous Amos (great cookies, great prophet) and why prosperity might be the harder spiritual test Obadiah the convert who saved 100 prophets from Jezebel, the rabbinic tradition that Rome is Edom, and the famous widow with the miraculous oil Micah and the morality prophets: how “idolatry” in our day reads as money, power, and the corruption that comes with success We also kept circling back to something: most American Jews don’t think about Gd as Someone with expectations. That’s exactly the tension Hosea was preaching into 3,000 years ago. Same story, different costumes. Hit play, and stay with us for Part 3, where we close out the Twelve.

Let’s be honest: when someone you’re not a fan of gets bad news, there’s a tiny, guilty dopamine hit. We open this episode by confessing that impulse out loud and digging into what Pirkei Avot (and King Solomon) have to say about rejoicing at your enemy’s fall. Spoiler: it’s a whole thing. In this episode, we get into: The ethics of Schadenfreude and what Pirkei Avot teaches about resisting that guilty satisfaction Shavuos 101: the forgotten major Jewish holiday, why your boss has never heard of it, and why it matters How the giving of the Torah turned a tribe into a nation (and why shared ancestry alone isn’t enough) The Sam Harris morality debate: can you have ethics without God? The trolley problem, Jewish style: why the Torah says you can’t pull the lever The Book of Ruth, the ultimate story of loyalty, conversion, and the origins of King David Whether you’re prepping for Shavuot or just want to know if you’re a bad person for enjoying celebrity gossip, grab some cheesecake and press play. 🧀 Episode References Pirkei Avot 4:19 Proverbs 24:17 The Ten Commandments Book of Ruth

The rabbi’s out this week, so we’re are doing what any self-respecting book nerds would do: geeking out about reading. In this episode, we get into: Jay breaks down his “30 pages a day” habit (spoiler: it adds up to 10,000 pages a year) ChayaLeah confesses her Shakespeare regrets Jay’s system for building a daily reading habit (and why you should keep three books going at once) The “Chan-book-ah” book haul: Arab nationalism, Elie Wiesel, Holocaust memoirs, and Jewish prayer ChayaLeah’s pitch for Cultural Amnesia by Clive James and why Remains of the Day is still on her mind Why understanding Jewish prayer word by word is a total game changer Life and Fate by Vasily Grossman, a book they both call the best they’ve ever read Hopefully you’ll get some ideas for your next book from this episode. Quote of the episode: "I realized I was never going to be the smartest person in a room, but I could be the most well read." — Jay All the books we mention: Arab Nationalism in the Twentieth Century by Adeed Dawisha God in Search of Man by Abraham Joshua Heschel Souls on Fire by Elie Wiesel Sages and Dreamers by Elie Wiesel Night by Elie Wiesel The Last Consolation Vanished by Zalmen Gradowski Hostage by Eli Sharabi On Killing by Dave Grossman Elusive Prophet: Ahad Ha’am and the Origins of Zionism by Steven Zipperstein As a Driven Leaf by Milton Steinberg Anonymous Soldiers by Bruce Hoffman To Pray as a Jew by Hayim Halevy Donin The Hour of Our Death by Philippe Ariès Arrows of the Dark (two volumes) by Tuvia Friling Life and Fate by Vasily Grossman The Road by Vasily Grossman Cultural Amnesia by Clive James Remains of the Day by Kazuo Ishiguro The Facemaker by Lindsey Fitzharris My Prayer (two volumes, Chabad teachings on prayer) — could not confirm Amazon listing, may need manual search Rebel and Statesman-The Early Years: The Life and Times of Vladimir Jabotinsky: Volume One by Joesph Schechtman Fighter and Prophet; The Jabotinsky Story; The Last Years by Joesph Schechtman The Bronze Horseman by Paullina Simons - this is ChayaLeah’s book. Jay dissavows

What does it actually take to be a prophet? Spoiler: it’s not just hearing voices and shouting in the marketplace (though there’s some of that). In this kickoff to our new series on the Trei Asar, the Twelve Prophets of the Tanakh, we set the stage before diving into the individual books. Think of this as Prophecy 101 with a side of cult talk, because honestly, the line between “biblical prophet” and “guy with millions of YouTube followers” is thinner than we’d like to admit. In this episode, we get into: 📜 What prophecy actually is in Judaism, according to Maimonides, and why Moses was working on a totally different frequency from everyone else 👑 The three pillars of Jewish leadership (king, high priest, Sanhedrin), and where the prophet fit 🎤 Who got tapped to be a prophet, why some were reluctant 🚫 Why prophecy ended after Haggai, Zechariah, and Malachi, and what replaced it 🤔 What we’d actually do if a prophet rolled up today (hint: probably an institution) 😬 False prophets and cults like, Sabbatai Zvi, Jim Jones, the Moonies Get ready to learn everything you ever wanted to know about prophecy but were afraid to ask.

King Solomon had a thousand wives, wrote a book of proverbs, and still felt the need to write a whole passionate love poem about a shepherd boy and a maiden. Coincidence? We think not. In this follow-up to our Valentine’s Day episode, we go deeper into what Judaism actually teaches about love, including what Song of Songs reveals about God’s relationship with the Jewish people, and we bring it all the way down to earth with real talk about marriages stuck in a rut, whether people can truly change, and why “I can’t” usually means “I don’t want to.” In this episode, we get into: Shir HaShirim (Song of Songs): literal love poem or divine allegory? Why love is the only personality trait with its own dedicated book in the entire Hebrew Bible What Adam and Eve tell us about whether opposites actually attract Why real love has nothing to do with infatuation, Hollywood, or Taylor Swift (though we do have opinions about her and Travis) Practical advice for married couples who have drifted apart and want to find their way back Trust vs. love: which one is actually the foundation of a lasting relationship The Baal Shem Tov’s classic “you can, you just don’t want to” and why it applies to your marriage right now Why the Rebbe and Rebbetzin’s relationship might be the greatest love story you’ve never heard "Love goes deeper than what you can do for me. You love the person for who they are and what they are, not what they do for you." — Rabbi Whether you're happily married, newly in love, or just trying to remember what you liked about the person across the breakfast table, this episode has something real for you. Come learn, laugh, and maybe text your spouse something nice when it's over. 🕯️❤️ Referenced Material- Shir HaShirim (Song of Songs) Kohelet (Ecclesiastes) by King Solomon Mishlei (Proverbs) by King Solomon

We’re kicking off a brand new segment called “Dear Rabbi,” where we bring real-life issues to the Rabbi and actually get into it with honest, often hilarious, sometimes painful conversations about the stuff people are quietly struggling with. First up: how to care for elderly parents without losing your mind, your marriage, or your lunch break. In this episode, we get into: Setting boundaries with elderly parents (and why that’s easier said than done) The difference between being a caregiver and being a nurse Why your parents just want to feel significant — and no, a text does NOT count The generational divide around phones, Uber apps, and why nobody remembers their Kaiser password What to do when your relationship with your parents is, well, complicated The Rabbi’s reflection on his Holocaust-survivor father and putting yourself in your parents’ shoes Jay on caring for his mom while raising a young daughter and feeling guilty about feeling guilty ChayaLeah admitting which of her four sons she’d trust with her medications (spoiler: it’s not all of them) Plus a hot take on Matzo manufacturers who dare to sell non-Kosher-for-Passover matzo. The audacity. Whether you’re navigating aging parents yourself, trying to figure out how much you’re really capable of giving, or just looking for permission to laugh about the hard stuff, this one’s for you. Grab a coffee, settle in, and remember: your parents just want you to call. Got a question for Dear Rabbi? Email us at edjewcationpod@gmail.com or message us on Substack.

We kicked off this month's Zoom talking about the Rebbe's birthday and why his legacy still hits so hard, from growing Chabad's global mission to his no-nonsense philosophy on turning obstacles into opportunities. Then we got into full Passover mode: ChayaLeah is prepping a community Seder for 120 people and her game plan is SPEED. We broke down the Ten Plagues (why those plagues, why that order, and how long they actually lasted), talked about why you don't need a minimum number of people for a Seder (but the more the merrier), and heard from Moshe Perelmuter live in Israel about what Passover looks like during wartime, with packed grocery stores but empty Jerusalem streets. We also explored studying the Tanya, which the Rabbi describes as essentially a self-help book for the Jewish soul. And Goldie dropped some hilarious childhood stories about sharing a bedroom with ChayaLeah. It's Passover prep meets life advice meets family chaos.

On this chag episode, we tackle a section of the Haggadah that almost everyone breezes past: Jacob's fateful decision to "temporarily" settle in Egypt, only to buy land, put down roots, and stay for 17 years. From that ancient real estate deal, the conversation spirals into the big questions Jewish families are wrestling with right now: What does Israel really mean to diaspora Jews? Is "dual loyalty" just an antisemitic trope, or something worth actually thinking about? Why did 80% of Jews choose to stay in Egypt even after centuries of slavery? We don't talk about rising antisemitism, the war with Iran, and what it means to say "Next year in Jerusalem" from your living room in Long Beach. ChayaLeah shares her family's Passover prep rituals (poster boards, car detailing, kids moving the fridge), and we a passionate case that any level of observance counts. Don't let the perfect be the enemy of the good. 🍷\ Resources Mentioned- Genesis 46:27 - Jacob’s family settling in Egypt Exodus 13:18 - Circuitous route out of Egypt The Four Questions explained - Chabad.org The Rebbe’s seder table - Chabad.org