The JTrain Podcast

Jared kicks off Chit Chat Wednesday in Delray with John Gabrus, and they immediately “break up” as friends because Jared moved to Florida without telling him. They bond over midlife “why didn’t I just live near a beach?” energy, then detour into comedy-world gripes, including how movies love stunt casting when there are a thousand actual funny comics available. Gabrus shares his peak midlife-crisis triumph: a solo Mexico trip for surfing and intensive Spanish classes to get off his phone and feel alive again. They then end by playing a Hillstone menu game that reveals Jared is Team Girl Lunch while Gabrus is Team Steakhouse Dad. They promise to finally hang out, which in podcast terms means it might happen sometime before the next Ice Age.Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendFind and cancel your unwanted subscriptions with Rocket Money at https://www.rocketmoney.com/JTRAIN Eat smart @ http://factormeals.com/jtrain50off & use code jtrain50off to get 50% off your first box, plus Free Breakfast for 1 year.

Jared opens Ticked Off Tuesday from Delray and immediately roasts himself for showing up to “the hottest restaurant in Delray” on Christmas Eve…only to realize his reservation was for January 1, 2026. He then spirals into beach-walk social awkwardness and floppy-hat groups refusing to go single file. The big vent is Delta, where he claims the airline hides his hard-earned upgrades in the app like a toxic partner gaslighting him about their “benefits.” Listener complaints bring the chaos: a hungover flyer forced to watch a seatmate bite and display nail clippings like tiny trophies, a university worker exhausted by parents doing adult kids’ basic tasks, and a mother-in-law who treats dinner parties like an HGTV intervention. Overall, petty grievances, Florida sunshine, and Jared turning everyday annoyances into a full-on comedy sport!Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Jared kicks off the real first Monday of 2026 with Mailbag Monday energy, reminding listeners that resolutions start now and inviting everyone to put their brain on the shelf. The first email comes from a self-proclaimed “classy” guy spiraling over a friend’s engagement ring he finds tacky, and Jared’s advice is simple: if no one asked for feedback, keep it to yourself. Next, a listener admits she’s stuck in a two-year-long-distance situation with a man who has never wanted commitment, while dating a “nice and consistent” guy she feels less excited about, and Jared delivers tough love that she’s chasing vacation-mode potential, not a real relationship. Finally, a listener feels awkward chasing friends for Venmo pizza money. Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Jared kicks off the New Year by breaking down celebrity headlines of the week! From Jeff Bezos allegedly commissioning a statue of Lauren Sanchez to Brooks Nader turning a belt into a top, Jared unpacks the absurdity of wealth, beauty standards, and attention economics. He also calls out Elizabeth Hurley’s unrealistic bikini “tips,” dives into Cardi B’s clapbacks, and dissects how Page Six fills slow news weeks. A smart, funny look at celebrity PR strategies, critical thinking, and why pop culture is still so entertaining!Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Jared kicks off Chit Chat Wednesday with comedian Caitlin Peluffo, joking about her life as a road warrior and the reality of touring, from romanticizing small towns to surviving bleak winter clubs on comedy club coffee. Caitlin gives a Hallmark-level rundown of her parents’ over-the-top 55+ community Christmas setup, complete with gingerbread villages, reindeer plaques, and stockings with old-school oranges. She also shares why being single is her current glow-up: no emotional management, no long-distance stress, just peace, vibes, and group chats. They wrap with a goofy round of “Flabby or Fab,” shout out to Caitlin’s upcoming shows, and agree that a Zingerman’s sandwich in Ann Arbor is non-negotiable!Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend