The JTrain Podcast

Latest Episodes:

West Tells His Side, Dave Chappelle Receives a Gift, and Haylie Duff’s Cursed Life - POP CULTURE THURSDAY Apr 23, 2026

Show notes

Pop Culture Thursday with Jared breaking down celebrity news and drama 👇

Haylie Duff and Matt Rosenberg split after 12 year engagement
West Wilson responds to dating scandal timeline
Dave Chappelle gifted $7K beeswax sculpture in random NYC moment
Taylor Swift and Travis Kelce wedding guest drama with Zoë Kravitz rumors

Support the podcast by supporting our sponsors!

Don’t sleep on @ultrapouches. New customers get 15% off with code JTRAIN at http://takeultra.com #UltraPouches #ad

Meet And Greet Line Horror Stories with Brad Williams - CHIT CHAT WEDNESDAY Apr 22, 2026

Show notes

Jared sits down with road comedy expert and stand-up Brad Williams! Check out his new special, Live on Short Street, out now! The two talk 👇

Why “on tour” never actually ends
Celebrities trying stand-up vs comics who grind it out
Meet-and-greet moments that go way too far
Weird hotel habits that keep comics sane
The story behind Live on Short Street

Jared is on tour! 👉 jaredfreid.com

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

Support the podcast by supporting our sponsors!

Don’t sleep on @ultrapouches. New customers get 15% off with code JTRAIN at http://takeultra.com #UltraPouches #ad

App Updates, Mobile Coffee Orders, and Amex Offers - TICKED OFF TUESDAY Apr 21, 2026

Show notes

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇

Constant useless app updates with no real changes
Miami life shock: aggressive drivers and rude grocery store behavior
Amex credit denied because spouse used a different card on same account
Coffee shops favoring mobile orders over people standing in line

Jared is on tour! 👉 jaredfreid.com

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

Support the podcast by supporting our sponsors!

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

Get up to 80% off this Way Day, with fast & free shipping on everything @ http://Wayfair.com

Going On A Date With An Old Hookup, How Do I Make It Real This Time? - MONDAY MAILBAG Apr 20, 2026

Show notes

It’s Mailbag Monday, and Jared is giving advice on 👇

Am I ruining the romance by not letting him fully handle and pay for the proposal?
Reconnecting with a past hookup on Hinge, but I want it to be serious this time
Boyfriend in a wild sports group chat called the “Titty Committee” - ew

Jared is on tour! 👉 jaredfreid.com

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

Support the podcast by supporting our sponsors!

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

Get up to 80% off this Way Day, with fast & free shipping on everything @ http://Wayfair.com

Alix Earle vs Alex Cooper, Kelly Ripa's Son On Broadway, and Howard Stern - POP CULTURE THURSDAY Apr 16, 2026

Show notes

Pop Culture Thursday and Jared covers👇

Alex Cooper vs Alix Earle: podcast fallout and TikTok drama
Jenny Garth & Tiffani Thiessen: 90210 friendship fallout
Howard Stern: ex-assistant lawsuit and workplace drama
Paris Hilton: Coachella bathroom moment and VIP life
Drew Sidora & Ralph Pittman: divorce and income gap plus Kelly Ripa & Mark Consuelos son Joaquin Broadway debut

Support the show, support the sponsors!

Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/jtrain #rulapod #ad

Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

The Making of Walking Red Flag with Taylor Kay Phillips - CHIT CHAT WEDNESDAY Apr 15, 2026

Show notes

Jared is joined by comedian & ghostwriter Taylor Kay Phillips to talk dating, writing, and life behind the scenes of his new book, Walking Red Flag! They talk 👇

Inside ghostwriting and writing Walking Red Flag
Dating advice for modern relationships and honesty
They play: Banana or Raspberry

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, support the sponsors!

Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/jtrain #rulapod #ad

Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

Supermarket Return Policy, Hotel Patios, and Giant Baseball Stadium Beer Cans - TICKED OFF TUESDAY Apr 14, 2026

Show notes

It's Ticked Off Tuesday! Jared reviews listener frustrations👇

Hotel patio woes are interrupting a getaway
Thank you note timing gone wrong
Trouble finding late-night dining spots
MLB ballpark oversized beer problems

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

New customers can use code jtrain50off to get 50% off and free daily greens per box at http://FactorMeals.com/jtrain50off

Why Does Raya Suck? - MONDAY MAILBAG Apr 13, 2026

Show notes

Jared is answering 3 listener emails this Mailbag Monday!👇

Acted like the love of my life… then he ghosted
Life after Mormonism and friendship burnout
Why is Raya impossible to quit?!

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

New customers can use code jtrain50off to get 50% off and free daily greens per box at http://FactorMeals.com/jtrain50off

Patriots Coach, Jason Derulo on Being “37 & Single,” and Ryan Seacrest’s Red Flags - POP CULTURE THURSDAY Apr 09, 2026

Show notes

It's Pop Culture Thursday and Jared is breaking down the biggest celebrity stories of the week 👇👇

Jason Derulo comments on being 37 and single
Secret Lives of Mormon Wives cast drama and Taylor Frankie Paul fallout
Patriots Coach & NFL Reporter hand-holding hotel story
Ryan Seacrest shares bizarre dating “red flags”
Rod Stewart’s wife Penny Lancaster says she deserves a medal for marriage

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, support the sponsors!

Get $2.99 per meal on your first box & 10% off for 1 month with code jtrain299 at http://everyplate.com/podcast

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

How Austin Has Changed with Jamie Kilstein - CHIT CHAT WEDNESDAY Apr 08, 2026

Show notes

Jared is joined by comedian Jamie Kilstein for a funny, honest Chit Chat Wednesday about 👇

Moving to Florida, Austin, and life outside NYC / LA
Why comedy got weird in Austin!
Making risky jokes actually funny
They play: Woke or Broke!

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, support the sponsors!

Get $2.99 per meal on your first box & 10% off for 1 month with code jtrain299 at http://everyplate.com/podcast

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

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