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!

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

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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.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 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.com

Check 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.com

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

Ticked Off Tuesday kicks off with Jared roasting the podcasts that “took the week off,” declaring Best Of episodes basically a slap in the face when everyone needs comfort-content most. Then he vents about the Paul brothers making an absurd $92 million boxing a pro. His main chaos story is an Orlando show where late arrivals spent eight full minutes loudly ordering drinks  mid-set. Listener rants pile on: speakerphone calls on a 7am NYC train, a beloved best friend whose “maximalism” has become full trash ecosystem, and a budget massage place that tried to demand a $20 tip like it was an entry fee. He closes with a very millennial-sounding housing/internet nightmare that turns into a realization: we are forever the test generation, getting whiplash from “your building only has AT&T” to “lol it’s all in the air now.”

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

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com

Mailbag Monday lands in the weird, snack-filled limbo between Christmas and New Year’s, and Jared proudly reminds you that while other podcasts are “resting,” Uncle J Train is still clocking in. He tackles a Hallmark-level dilemma about crushing on a cute, ring-free optometrist and how to shoot your shot without turning it into a LinkedIn crime scene. Then he breaks down the “fifth date shut down” question and why silence afterward can actually be a helpful answer for both people. The episode takes a surprisingly sweet turn with a one-year-later follow-up from a listener who finally said “I love you” after a divorce—and it worked—sending Jared into full sentimental mode. It’s equal parts dating advice, gentle pep talk, and holiday-season camaraderie.

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

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com

On this special episode of the JTrain Podcast, Jared Freid breaks down the week in pop culture, from Brooklyn Beckham’s family drama to Jennifer Lopez and Ben Affleck’s headline-making relationship, plus updates on Tom Brady and Gisele Bündchen. The conversation also hits celebrity love lives and media scrutiny surrounding Ariana Grande, Amy Schumer, Lily Allen, and influencer culture through Alix Earle. With sharp humor and honest takes, Jared explores how fame, social media, and public opinion complicate relationships, whether you’re a global superstar or just living online!

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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On this Chit Chat Wednesday, Jared sits down with comedian Lukas Zelnick for a hilariously chaotic hang where they start as “not-not friends” and immediately bond over tech hiccups and NYC apartment humblebrags. From Soho loft lore and moving-in-with-a-girlfriend growing pains to the weird psychology of being “the rich kid who owns it,” Lukas breaks down how his background became part of his comedy voice. They get into crowd work vs. polished standup, why timing and the internet changed how comics build an audience, and the pressure of putting out a special before you’re ready. Then Jared caps it all off with a rapid-fire “How Rich Are You?” game that spirals into tuxes, oysters, college allowances, and one extremely rich older brother reveal. It’s comedian shop talk meets playful roasting, with plenty of NYC energy in between.

Jared is on tour! 👉 jaredfreid.com

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

Find and cancel your unwanted subscriptions with Rocket Money at https://www.rocketmoney.com/JTRAIN