The JTrain Podcast

00:28:03

Is A Matchmaker Worth It? - MONDAY MAILBAG

The JTrain Podcast ·

2026/06/22

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

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00:42:40

Jelly Roll Gets Divorced, Brunson Named "King Of New...

The JTrain Podcast ·

2026/06/18

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

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00:33:11

Why Dating Got Harder AFTER Netflix Fame! ft Caitlin...

The JTrain Podcast ·

2026/06/17

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

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00:35:48

Starbucks Bathroom Etiquette, Reservation Hoarders,...

The JTrain Podcast ·

2026/06/16

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

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00:25:52

I'm Invited to a Wedding Where Everyone Has to Wear...

The JTrain Podcast ·

2026/06/15

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

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00:39:30

Kim Kardashian's PDA at F1, Morgan Wallen Throws A...

The JTrain Podcast ·

2026/06/11

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! 👉

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00:43:58

Why NPR Credits Don’t Work in Comedy ft Ophira Eisenberg

The JTrain Podcast ·

2026/06/10

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.com Check out his new book! 👉

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00:33:48

My In-Laws Won't Give Money For Our Wedding Until...

The JTrain Podcast ·

2026/06/09

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 starts Jared is on tour! 👉 jaredfreid.com Check out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy Friend Support the podcast by supporting our sponsors! Get 40% off select Lola Blankets

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00:40:13

They're Watching My IG Stories! What Does it Mean? -...

The JTrain Podcast ·

2026/06/08

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 Friend Support the podcast by supporting our sponsors! Get 40% off select Lola Blankets products at http://Lolablankets.com by using code

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00:51:09

Sydney Sweeney, Kendall Jenner, Jacob Elordi, and Dua...

The JTrain Podcast ·

2026/06/04

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

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00:59:13

Everyone Has the Same Opinion Now and It’s Weird! ft ...

The JTrain Podcast ·

2026/06/03

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.com Check out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy Friend Support the podcast by supporting our

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00:43:52

AP/Swatch Collab, Nutrition Facts, and Hot Hotel...

The JTrain Podcast ·

2026/06/02

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.com Check out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy Friend Support the podcast by supporting our

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01:01:33

Am I Being a Bridezilla about My Destination Wedding...

The JTrain Podcast ·

2026/06/01

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.com Check out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy Friend Support the podcast by supporting our sponsors! Support the show & get 10% off your Hero Bread order with

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00:30:13

Summer House Reunion, Scorsese's Daughter Has Trolls,...

The JTrain Podcast ·

2026/05/28

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Ciara Miller, West Wilson, and Amanda Batula: Summer House reunion dramaNepo baby debate reignites with Francesca ScorseseTaylor Swift spotted with Travis Kelce at NBA gameJacob Elordi pulled into injury clickbait confusionBarbra Streisand linked to fake Cannes injury storyJaclyn Smith at 80 reveals beauty secretAurora Culpo welcomes baby girl with fiancé Zach Jared is on tour! 👉

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00:40:04

The Internet Is Mad We Don’t Have Kids! ft Jim Tews -...

The JTrain Podcast ·

2026/05/27

Comedian and cartoonist Jim Tews joins Jared for a Chit Chat Wednesday! Be sure to check out his comedy special, With PicturesJim Tews turned his stand-up special into a cartoon comedy show Why the internet gets furious when people say they don’t want kidsJared and Jim debate whether weird comedy is disappearingThey play “No Excuse, Make Up An Excuse” gets painfully relatableJared is on tour! 👉 jaredfreid.com Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite

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00:35:44

Closed Marriott Concierge Lounges, Bad Massages, and...

The JTrain Podcast ·

2026/05/26

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇 Marriott concierge lounge closed on weekendsChicago parking nightmare made her 40 minutes lateDeep tissue massages with ZERO spa vibesLoud comedy crowd ruined the entire show!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!Get 20% off your first 6 months of Quo business communications at

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00:42:45

My Brother is Getting My Late-Grandmother's Ring!...

The JTrain Podcast ·

2026/05/25

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems!👇 We had a perfect date, and now he’s gone for 10 days, and I’m spiraling! help!I’m a 36 year old widow trying to date casually for the first time, and I have no idea what I’m doingMy little brother is getting my late grandma’s engagement ring, and I’m furious Jared is on tour! 👉 jaredfreid.com Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy

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00:33:30

Bethany Frankel's Shoe Drama and Hillary Duff Wears A...

The JTrain Podcast ·

2026/05/21

Pop Culture Thursday: Jared reads latest celebrity headlines from Page Six and gives his unfiltered takes!Bethenny Frankel shoe dramaHilary Duff on the cover of Sports Illustrated Swimsuit Issue 2026Justin Baldoni and Blake Lively legal drama Taylor Swift and Travis Kelce wedding updatesMandy Moore Reacts to Ashley Tisdale's EssayGwyneth Paltrow's daughter, Apple, lands major movie role Jared is on tour! 👉 jaredfreid.com Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from

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00:44:01

How to Get Financially Smart Without the Shame ft....

The JTrain Podcast ·

2026/05/20

It’s Chit Chat Wednesday with Financial expert Haley Sachs of Mrs. Dow Jones, who wrote a new book, Future Rich Person! The two talk 👇 money mindset, taxes, and building wealthdating and money in relationshipsgame: “How Rich Are You?”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! Sign up for Bilt & start earning points on your rent or mortgage

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00:40:04

Changing Our Language For The Dumbest People,...

The JTrain Podcast ·

2026/05/19

It's Ticked Off Tuesday and Jared is complaining with YOU about 👇 Jared's ticked off at TikTok!Every business begging for reviews after every single thing you doAirline furniture delivery chaos and weird rules that ruin simple fixes!Dog owner drama from lost dogs to messy bad pet habitsMother’s Day pressure family plans and emotional guilt trips Jared is on tour! 👉 jaredfreid.com Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend Support the

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