It’s Chit Chat Wednesday, and Jared is joined by comedian Raanan Hershberg, whose new YouTube special Morbidly Jewish sparks a thoughtful, funny conversation about comedy, controversy, and why labels kill nuance. They dig into what it’s like doing standup in a time when even obvious jokes about bad people somehow become “debates.” From antisemitism discourse to why audiences sometimes seem offended by the mere act of joking, it’s a ranty, smart back-and-forth on why comedy still matters. Then things take a turn toward food, where the two bond over Katz’s Deli, gluttonous pastrami sandwiches, and the chaos of ordering as a team.

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Jared is back for Ticked Off Tuesday, begging people to keep weed smoke out of restaurant entrances and to stop treating the front of the coffee line like storytime. Then he spirals over Threads being less “fun alternative” and more “comics loudly arguing in public for sport.” A listener points out that one little snowstorm turns grocery stores into pre Hunger Games chaos, which… fair. Another vents about a networking call getting flaky canceled, and a newlywed discovers name changes make TSA PreCheck a bureaucratic nightmare. But the funniest rage is a brand new mom who’s running on fumes while her husband randomly starts logging baby feedings in military time, sir, read the room!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

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Mailbag Monday is in full “tough love, but make it helpful” mode as Jared breaks down three modern dating headaches: the ex who keeps popping up with cryptic, ego-soaked poetry, the couple doing “ethical non-monogamy” that somehow feels like a sad group project, and the doctor who’s back a year later claiming the relationship ended because you “didn’t believe he was busy.” Jared’s main theme is clear: you don’t need a courtroom-level case to leave someone who makes you feel emotionally unsafe, and you definitely don’t owe your time to people who rewrite history to avoid accountability. He also goes on a mini-rant about how we digest texts like they’re meals (and why blocking is sometimes self-care). Equal parts funny, blunt, and weirdly calming, like having a friend grab your phone mid-spiral and go, “Nope. We’re not doing this today.

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Get 40% off your entire order at http://Lolablankets.com by using code JTRAIN at checkout. Experience the world’s #1 blanket with Lola Blankets.

Visit https://prizepicks.onelink.me/LME0/JTRAIN & use code JTRAIN to get $50 in lineups when you play your first $5 lineup!

Pop Culture Thursday is back and Jared Freid is deep in Page Six chaos, riffing on Prince Harry and Meghan Markle’s fading industry buzz, paywalled celebrity news, and why having an audience isn’t the same as earning trust. He breaks down Joe Montana “laughing all the way to the bank,” Tom Brady’s endless shilling, and why certain headlines are catnip even when the articles disappear mid-read. Jared also dives into the messiest drama of the week: Taylor Swift’s private texts leaked amid Blake Lively and Justin Baldoni’s legal battle, unpacking friendship “vibe shifts,” exposed group chats, and why released texts feel naked no matter who you are. Plus, he side-eyes Heidi Klum’s new self-produced documentary, her much-younger “hot” husband Tom Kaulitz, and the rise of celebrity propaganda, before wrapping with Olympian Gus Kenworthy, Miley Cyrus, and Heated Rivalry parallels ahead of the Olympics!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

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Katie Nolan crashes Chit Chat Wednesday and she brings sports chaos: Pats/Bears misery bonding, the sacred “don’t celebrate until it’s confirmed” PTSD that only real fans understand, and Katie breaking down why the Super Bowl is basically a corporate convention with occasional football. Then Jared drops the ultimate peace treaty idea: make political candidates order Buffalo Wild Wings together before debating… which leads to an absurdly detailed, oddly unifying wing order negotiation (bone-in vs boneless diplomacy included). It’s fast, funny, and somehow wholesome, like yelling about football and fries with a friend who actually gets it!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Get your first 3 Months of GLP-1 treatments for $133 a month with code JTRAIN at https://www.brelloheath.com/

Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Ticked Off Tuesday is firing on all cylinders as Jared unloads on weather-watchers who treat his tour schedule like a group chat emergency, complete with unsolicited storm anxiety. Listener complaints roll in hot, including getting ripped off on game tickets because “that’s just what it costs,” a luxury flight that turned into unpaid service supervision, and an assistant who can’t stop calling to clarify tasks that could already be done. Then Verizon enters the chat by offering to mail a password reset in the year 2026, somehow topping everything else. It’s petty, cathartic, and deeply validating for anyone who’s ever whispered “am I crazy?” at their phone. Come for the complaints, stay for the reminder that you’re not alone in losing your mind over modern nonsense.

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show and get $10 off your 1 st month of Nutrafol. Head to https://www.nutrafol.com & use code FEATHER

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It’s Mailbag Monday from Delray Beach, and Jared’s inbox is doing what it does best: exposing the chaos we all pretend isn’t happening. First up, a “situationship” that’s giving off mysterious relationship anxiety vibes, an age gap, daily drinks, and a whole lot of “we” language for something that isn’t actually a “we.” Then a freshly single 31-year-old wonders if her breakup for political differences was valid. Was her breakup valid? Finally, a NYC listener needs a birthday dinner strategy when her favorite one-on-one friend turns into a group-setting chaos grenade. Jared lays out the only real options: set boundaries, make it their choice, or keep the reservation (and your peace) on lockdown!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show and get $10 off your 1 st month of Nutrafol. Head to https://www.nutrafol.com & use code FEATHER

Get 25% off all mattresses PLUS an extra $50 off with code JTRAIN at http://Leesa.com

This episode Jared dives headfirst into the Beckham family drama, unpacking Brooklyn Beckham’s explosive statement about David Beckham and Victoria Beckham, the wedding dance controversy, and the celebrity fallout that followed. From Nicola Peltz Beckham and billionaire in-laws to Mark Anthony, Bethenny Frankel, and Lily Allen weighing in, Jared riffs on money, control, image, and modern family loyalty. The episode also touches on Kristin Cavallari’s dating regrets as a mom, celebs picking sides, and why airing family feuds on social media almost always backfires. A classic Page Six breakdown with sharp takes, humor, and zero chill.

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN