Jared is joined by comedian, friend, and certified SVU expert Liza Treyger for an unhinged Chit Chat Wednesday that covers everything from drinking on flights to the strange social hierarchy of Delta Comfort. The two bond over airline loyalty, missed upgrades, and the humiliation of milestone flyers getting celebrated nowhere near first class. Liza dishes on tour life, ticket selling honesty, and why she’s fully in her “drinking on planes” era, while Jared proudly plays hype man for her upcoming shows. Things take a sharp turn into pop culture obsession as Liza passionately breaks down why Heated Rivalry has completely taken over her brain, her libido, and possibly modern feminism. Along the way, they debate sex scenes, consent, power dynamics, and why straight men may need to take notes. The episode wraps with a surprisingly revealing game of “what would you order” at Applebee’s, proving once again that food choices say everything about a person.

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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 Ticked Off Tuesday from Delray by inviting listeners to vent freely, then launches into his own “rich person problem” that still feels brutal: he finally plays at the legendary Torrey Pines golf course, only the rough is so tall the course basically has a “lose your ball, no penalty” rule. Next, he’s mad that junk mail now cosplays as urgent, then listener complaints keep the petty parade going. A mother-in-law’s condo is gorgeous but has “museum couch” energy, Boston tenants are stuck doing snow and trash while the owner only leaves passive-aggressive notes, and a gym busybody tries to shame someone out of their second massage-chair session. He wraps with the universal rage of car rentals.

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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Jared opens Mailbag Monday from Delray with gratitude, beach energy, and a reminder that anonymous advice hits harder than biased friends. The standout email comes from a listener who went on six “pretty good” dates and can’t stop thinking about bunny-rabbit sex, being asked to fetch latkes, and having to share a single hot dog at a hockey game. Jared’s verdict is clear and funny: if it’s still only “pretty good” after six dates, that’s already your answer. He reframes dating like investing, asking whether this relationship could realistically get 10 percent better and become a life you actually want. The lesson is not that she’s too picky, but that chemistry matters more than politeness and settling only builds resentment. Classic JTrain delivers a warm hug, a reality check, and permission to move on without guilt!

Jared is on tour! 👉 jaredfreid.com

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

Get $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast

Pop Culture Thursday has Jared breaking down Ashley Tisdale opening up about toxic mom groups and why it hits home for millennial women. He also gets into Amy Schumer’s Instagram post during her divorce and what it says about body image and fame. Plus, Cher weighs in on Kristen Bell and Dax Shepard, and why trips to St. Barts make celebrity drama even louder!

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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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.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

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.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

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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