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!