The JTrain Podcast

Taylor Swift Wedding Timeline, Menu, and Travis Kelce's Pre-Wedding Routine - POP CULTURE THURSDAY 02.07.2026 28min

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Taylor Swift and Travis Kelce's MSG wedding plansTaylor Swift wedding menu revealedMSG lockdown for Taylor Swift weddingKyle Cooke and Ava Dash romance rumorsRob Kardashian's rare family appearanceJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!For free shipping on your order & 365-day returns go to https://www.Quince.com/JTRAIN

The Reality of Joining Instagram Later in Life! ft Emmy Blotnick - CHIT CHAT WEDNESDAY 01.07.2026 45min

Comedian Emmy Blotnick joins Jared to talk about her new special, What's Her Secret? They talk👇Social media vs. stand-up comedySephora, skincare, and beauty cultureJapan travel and culture shocksKevin Hart roast behind the scenesCommercial jingles and Skyrizi adsThey play: Would You Watch?Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!For free shipping on your order & 365-day returns, go to https://www.Quince.com/JTRAIN

Facebook Marketplace, People with Fake Allergies, & Online Clothing with Only ONE Picture - TICKED OFF TUESDAY 30.06.2026 35min

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇People on Facebook Marketplace are expecting delivery for free items!Asking for medical advice in checkout lines backing up the line!Online stores with too few product photos!Audiobook apps that never save your place correctly in the car! Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN

How Do I Keep The Momentum Going With A Guy During My Summer Travel? - MONDAY MAILBAG 29.06.2026 40min

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 How do I support my fiancé's younger sister without getting too involved in her life?Should I push my longtime friend to start dating or let him figure it out on his own?How do I tell the guy I'm dating I want to keep seeing him after my month away without making it a big relationship talk? Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN

Dianna Russini's Salary, Taylor Swift's Surprise Show, and Jewel's Stealing Addiction - POP CULTURE THURSDAY 25.06.2026 35min

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!👇Taylor Swift joins Lainey Wilson at Travis Kelce's Tight End University eventLeslie Jones on SNL typecastingDiana Rossini's crazy salary revealed amid Mike Vrabel scandalJewel opens up about homelessness and shoplifting addictionClive Davis dies at 94, remembered by Bruce Springsteen and Whitney Houston collaboratorsJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Sign up for Bilt & start earning points on your rent or mortgage payments. Just go to http://JoinBilt.com/JTRAIN

What's It Like To Write For A Roast ft Nicole Becannon - CHIT CHAT WEDNESDAY 24.06.2026 30min

Jared sits down with comedian and roast joke writer Nicole Becannon, who shares how the biggest comedy roasts are written behind the scenes.Writing jokes for the Kevin Hart RoastHow roast writing actually worksThe art of making jokes landThey play: Roast Joke Draft!Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Sign up for Bilt & start earning points on your rent or mortgage payments. Just go to http://JoinBilt.com/JTRAIN

Train Signage, Hosting A Friend's Birthday, and Cashiers - TICKED OFF TUESDAY 23.06.2026 30min

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇 Why Costco only has GIANT carts for quick shopping tripsDoing ALL the work for a party and getting left out of photosHairdresser's noisy bracelet RUINING a long hair appointmentA cashier turning a quick checkout into a FULL conversationJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport 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

Is A Matchmaker Worth It? - MONDAY MAILBAG 22.06.2026 28min

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 Skipping a destination wedding when vacation days are limitedWhether matchmaking is worth the money or just like dating appsReaching out to an ex situationship ok? Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport 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

Jelly Roll Gets Divorced, Brunson Named "King Of New York," And Brooklyn Beckham - POP CULTURE THURSDAY 18.06.2026 42min

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Jelly Roll and Bunny XO divorce after his major weight loss journeyBunny XO's cryptic posts spark breakup speculation90 Day Fiancé stars Jenny Slatten and Sumit Singh discuss their s*x lifeBrett Eldredge reveals secret wedding to mystery womanKnicks championship party with Jalen Brunson, Josh Hart, OG Anunoby, & Karl Anthony Towns!Brooklyn Beckham takes a swipe at David and Victoria Beckham in new ad campaignJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

Why Dating Got Harder AFTER Netflix Fame! ft Caitlin Peluffo - CHIT CHAT WEDNESDAY 17.06.2026 33min

Caitlin Peluffo joins Jared to talk about her hit special Prosciutto Rose! g• Prosciutto Rose and writing honest comedy • Behind the scenes of Funny AF • Dating after reality TV success • Weird DMs and fan interactions • Game: Walking Red Flag or Wife MaterialJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Go to https://OmahaSteaks.com and use promo code JTRAIN at checkout for $35 off. Minimum purchase may apply.

Starbucks Bathroom Etiquette, Reservation Hoarders, and Kindle Updates - TICKED OFF TUESDAY 16.06.2026 35min

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇NYC dinner reservations feel like winning the lottery just to eat outTicketmaster makes changing Broadway seats harder than changing flightsElevator etiquette is confusing. Do I let strangers press my floor?Kindle updates feel forced just to keep downloading booksJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

I'm Invited to a Wedding Where Everyone Has to Wear Blue! Is That Crazy? - MONDAY MAILBAG 15.06.2026 25min

It’s Mailbag Monday and Jared is answering listener emails and gives advice on real life problems👇 Perfect boyfriend, no laughter. Is that a dealbreaker?Same office building as an ex. Do I say hi or avoid him?Blue-only formal wedding dress code. Do I really need a new dress?Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Kim Kardashian's PDA at F1, Morgan Wallen Throws A Phone, and Kyle Cooke Hooks Up - POP CULTURE THURSDAY 11.06.2026 39min

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Matt Damon on Hollywood vs fatherhood, 4 daughters, nonstop work lifeKim Kardashian ignores F1 reporter Martin Brundle at Monaco GP, sparks backlashRosie O’Donnell opens up about facelift, cost, and “shameful” commentsKyle Cooke linked to Southern Charm’s Sally Carson after Amanda Batula splitMorgan Wallen throws a fan’s phone off stage, sparks security and fan debateJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport 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 FEATHERNew customers can use code jtrain50 off to get 50% off and free daily greens per box at http://FactorMeals.com/jtrain50off

Why NPR Credits Don’t Work in Comedy ft Ophira Eisenberg - CHIT CHAT WEDNESDAY 10.06.2026 43min

This week's Chit Chat Wednesday is with Ophira Eisenberg! Comedian, former NPR host, and star of the new special I Used to Be Nicer. Ophira and Jared get into👇 NPR fame vs standup comedy identity Jacksonville crowds, TikTok backlash, and food opinions City pride, “where’s your Brooklyn,” and regional culture wars toxic positivity, manifesting, and parenting jokes airport wheelchair travel story and “VIP treatment” experienceJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport 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 FEATHERNew customers can use code jtrain50 off to get 50% off and free daily greens per box at http://FactorMeals.com/jtrain50off

My In-Laws Won't Give Money For Our Wedding Until They Know What My Parents Are Spending! Help! - TICKED OFF TUESDAY 09.06.2026 33min

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇 Neighbors hogging the shared laundry machinesLocked out of Facebook and Instagram with no customer supportWedding contribution drama between future in-lawsCoworker demanding updates before the workday startsJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Get 40% off select Lola Blankets products at http://Lolablankets.com by using code FEATHER at checkout. Experience the world’s #1 blanket with Lola Blankets.Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN

They're Watching My IG Stories! What Does it Mean? - MONDAY MAILBAG 08.06.2026 40min

It’s Mailbag Monday and Jared is answering listener emails and gives advice on real life problems👇 Why did she go silent after the setup?Coworker secretly watching your Instagram storiesHow to drink less and become an early riserJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Get 40% off select Lola Blankets products at http://Lolablankets.com by using code FEATHER at checkout. Experience the world’s #1 blanket with Lola Blankets.Get 20% off your first 6 months of Quo business communications at http://Quo.com/JTRAIN

Sydney Sweeney, Kendall Jenner, Jacob Elordi, and Dua Lipa Gets Married - POP CULTURE THURSDAY 04.06.2026 51min

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes! Sydney Sweeney claps back at critics over her Euphoria role Kendall Jenner & Jacob Elordi romance rumors with help from Justin Bieber and Hailey Bieber Horror movie Obsession becomes a surprise box office hit on a tiny budget! Janice Dickinson sparks plastic surgery debate, Dua Lipa marries Callum Turner! Jay-Z takes aim at Drake, Kanye West, and Nicki Minaj in a freestyle. Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show and update your outdoor space @ http://Wayfair.com

Everyone Has the Same Opinion Now and It’s Weird! ft Jamie Lee - CHIT CHAT WEDNESDAY 03.06.2026 59min

Jared sits down with Emmy-winning TV writer and comedian Jamie Lee, known for Ted Lasso and her solo show My Friend Katie, to talk 👇From brutal open mics to growing a standup voiceHow “pre-approved takes” shape what people think and say!They play 'This is Annoying' - real responses Jamie gets from working on Ted LassoJared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show and update your outdoor space @ http://Wayfair.com

AP/Swatch Collab, Nutrition Facts, and Hot Hotel Rooms - TICKED OFF TUESDAY 02.06.2026 43min

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇 AP/Swatch CollabPaid for TSA PreCheck but still stuck in the regular airport line!Starbucks tracks everything but sugar content is still unclearMiami hotel room turns into a sauna when the key is removedWhy do people expect movies to be realistic?!Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Am I Being a Bridezilla about My Destination Wedding in Italy? - MONDAY MAILBAG 01.06.2026 1h 1min

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 Why do guys on apps want my number so fast?Destination wedding planning: rules for plus-ones and family brunch I’m concerned with the stigma of GLP-1 Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the podcast by supporting our sponsors!Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co