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 nowThe 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 sameWhether settlement money is blood money, from an insurance check in America to the fight in 1950s Israel over taking German marksWhere 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 itWhat to say when a friend, a cousin, or a sibling drops “genocide” at dinner, who is worth engaging, and when to just walk awayYou 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 yearsWho pays for what, the fifty fifty split, and the gifts each side is expected to giveTakana 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 responsibilityThe 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 queenFasting on your wedding day, why it is considered a mini Yom Kippur, and the Rosh Chodesh loopholeThe badeken, the completely opaque veil, and the moment the next morning when the bride covers her hair for the first timeSheva Brachos, a full week of parties, and why the wedding is really a celebration of the entire familyCome 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 meansThe discrepancies with Numbers, starting with who really wanted to send the spies, plus the small differences in the Ten CommandmentsWho Moses is actually talking to: a generation born in the desert with no slave mentality and no memory of EgyptThe warning that prosperity, not persecution, is what makes people forget, and how uncomfortably well that lands in AmericaWhy Moses was not allowed to enter, what God showed him from the mountain, and why he wanted in so badly in the first placeThe 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 loveWe 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 usWhere the boundary sits, and how to give feedback that lands from a place of love instead of criticismProtecting your spouse first, and why in-laws have to tread more carefully than parentsRaising kids who become friendly with you without ever forgetting you are the parentFree choice, and how you can do everything right and still get a result you did not plan forOverbearing parents, helicopter moms, the Little League dad, and when to bring in a third partyWhether 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” propheciesThe scroll King Yehoyakim burned, and what Rashi says was in itWas Lamentations written before the destruction as prophecy, or after as eyewitness testimony?Why Jerusalem is described as a widow, and what that metaphor really meansThe Dubner Maggid’s parable of the needle-and-thread wagon: trading something real for nothingWhether Jews blame themselves too much for their own tragedies, from the Babylonians to October 7thWhy 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 placeThe trup (cantillation): how an ancient melody quietly narrates the story, including Joseph’s famous pause with Potiphar’s wifeGad and Reuben asking to stay east of the Jordan, and how one reversed word order exposed their prioritiesWhat the tribes’ obligation to fight alongside their brothers says about diaspora Jews when Israel is at warCities of refuge: the Torah’s “safe space” for accidental killers, and why the tribe of Simon got scattered on purposeWhether 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.LinksParashat 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 afterThe Rabbi’s own story of counting down the days, and the strange sadness when Kaddish endsThe five tragedies of the 17th of Tammuz and the start of the Three WeeksWhy 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 crossedThe Hanukkah menorah debate: do you start with eight candles or one, and why each side is rightThe gentile who asked to learn the whole Torah on one foot, and the very different answers Hillel and Shammai gaveWhy 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 lawWhy we almost always rule like Hillel, and the surprising reason it comes down to humilityPull up a chair, pick a side, and remember: the rest is commentary.Resources:Hillel and Shammai, sayings and characterMachloket 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 IsaiahNahum 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 faithZephaniah 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 otherGrab 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:MicahNahumHabakkukZephaniahHaggaiMalachi

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 doWhat a prophet (and a leader) is supposed to be: tough on the people, defender to Gd, never a politicianJoel and the locusts, the seven-year famine, and when punishment came measure-for-measureFamous Amos (great cookies, great prophet) and why prosperity might be the harder spiritual testObadiah the convert who saved 100 prophets from Jezebel, the rabbinic tradition that Rome is Edom, and the famous widow with the miraculous oilMicah and the morality prophets: how “idolatry” in our day reads as money, power, and the corruption that comes with successWe 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.