The JTrain Podcast

00:42:22

Who Should Pay for an Engagement Ring? Me or My BF?!...

The JTrain Podcast ·

2026/07/27

It’s Mailbag Monday and Jared is answering listener emails and gives advice on real life problems How do I set up two friends without making it awkward?Is she in the wrong marriage or chasing an unrealistic idea of love?Should I help pay for my engagement ring?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

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00:39:48

Matt Damon Mix Up, BBC Commentator Blunder and JLo's...

The JTrain Podcast ·

2026/07/23

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Matt Damon mistaken for Brad Pitt at FIFA World Cup finalJennifer Lopez bathtub birthday photos before turning 57BBC commentator confuses Pharrell with A$AP Rocky at World Cup finalSammy Sheen says Charlie Sheen has not given her money and credits OnlyFans for her successMegan Fox claps back after critics call her lingerie photos embarrassingJared is on tour! 👉 jaredfreid.comCheck out his

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00:45:00

Gen X vs Millennials In Love ft Des Bishop - CHIT...

The JTrain Podcast ·

2026/07/22

Jared is joined by comedian Des Bishop to talk about his new Hulu special, Bridge and Tunnel. Go watch it now! They also discuss 👇15 year age gap relationshipsWhy nostalgia is so powerfulNow or Then game: old vs new life choicesJared 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://cometeer.com/JTRAIN for $20 off your order!Support the show and update your outdoor

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00:27:58

People Singing At Fitness Class, Taking A Tour Of...

The JTrain Podcast ·

2026/07/21

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇Why am I handling my Starbucks delivery after paying for it?Why does airport etiquette disappear?Why do people cut coffee lines?Why did my Beyoncé spin class become karaoke?!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

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00:27:55

Do Men Care If I'm A Sweaty Date? - MONDAY MAILBAG

The JTrain Podcast ·

2026/07/20

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 Balancing a partner and aging parents as an only childI'm upset over a miscommunication for a last minute birthday celebration!How to handle sweating on a hot first date!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

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00:43:57

Arianna Grande's New Boyfriend, Page 6 Hates Rachel...

The JTrain Podcast ·

2026/07/16

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Howard Stern cuts back to one show a weekAriana Grande reunites with ex, Ricky AlvarezTom Segura and Christina Pazsitzky splitRachel Ray sparks new health concernsTaylor Swift and Travis Kelce's secret pet dog revealed!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

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00:44:50

Why I Posted My Crying Clip ft Eric Neumann- CHIT...

The JTrain Podcast ·

2026/07/15

Comedian Eric Neumann joins Jared to talk about his new special Call Your Mom, watch it today! They talk👇Calling his mom live on stageGetting notes from Ray Romano & Judd ApatowViral Knicks crying videoThey play: Would You Cry?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 40% off select Lola Blankets products at http://Lolablankets.com by using code FEATHER at

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00:35:40

Sound off for the World Cup, Packing Up Leftovers,...

The JTrain Podcast ·

2026/07/14

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇 Apartment canvassers have gone too farTiny airport bathroom stalls and suitcase strugglesHusband books an expensive vacation without askingAre restaurants making you pack your own leftovers?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!Find & instantly book doctors appointments with ZocDoc @

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00:33:14

Why Do My Hinge Matches Never Ask Questions? - MONDAY...

The JTrain Podcast ·

2026/07/13

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 Hinge matches that never ask questions backWarning a coworker about a possible performance reviewDating again after losing a sibling, and when to share itJared 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!Find & instantly book doctors appointments with ZocDoc @

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00:36:21

Taylor And Travis Have 20 Minute Vows, James Taylor...

The JTrain Podcast ·

2026/07/09

Pop Culture Thursday: Jared reads the latest celebrity headlines from Page Six and gives his unfiltered takes!Taylor Swift and Travis Kelce's insider wedding details: the menu, the no phone policy, and the 20 minute vowsHarry Styles' on stage wardrobe malfunctionLeonardo DiCaprio, Alix Earle, and Tate McRae escape to the Hamptons for 4th of July weekend Mike Tyson celebrates 60th birthday at Richie Akiva's celebrity filled Hamptons bashJames Taylor turns down Taylor and Travis' wedding

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00:41:45

I Got Hit By a Bus! ft Ryan Hamilton - CHIT CHAT...

The JTrain Podcast ·

2026/07/08

Chit Chat Wednesday with comedian Ryan Hamilton, talking about his new Netflix special, This Just Hit Me. Go watch today!.Avoiding podcasts and social media anxietyTurning a bus accident into comedyWriting a personal comedy specialThey play “Which Hits Worse?” 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!Connect with quality therapists & mental health experts who

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00:32:44

The 5 Worst Menu Items, Bridal Showers, and Upgrade...

The JTrain Podcast ·

2026/07/07

It's Ticked Off Tuesday, and Jared is complaining with YOU about 👇5 worst menu items!My Delta upgrade certificate disappeared after I changed my flight.I’m annoyed that restaurants now charge for chips and salsa.My family is guilt-tripping me for skipping a bridal shower.I’m frustrated by influencers making pregnancy look effortless after my IVF struggles.Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the

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00:34:27

Met a Guy at a Bar and He Ghosted! Why Waste My Time?...

The JTrain Podcast ·

2026/07/06

It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 I love my fiancé, but did I miss out on being single? I'm 25!I want my roommate to move out, but am I ruining our friendship?Why do people ghost after planning a date? 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

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00:28:18

Taylor Swift Wedding Timeline, Menu, and Travis...

The JTrain Podcast ·

2026/07/02

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

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00:45:51

The Reality of Joining Instagram Later in Life! ft...

The JTrain Podcast ·

2026/07/01

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

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00:35:32

Facebook Marketplace, People with Fake Allergies, &...

The JTrain Podcast ·

2026/06/30

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

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00:40:21

How Do I Keep The Momentum Going With A Guy During My...

The JTrain Podcast ·

2026/06/29

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

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00:35:47

Dianna Russini's Salary, Taylor Swift's Surprise...

The JTrain Podcast ·

2026/06/25

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

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00:30:50

What's It Like To Write For A Roast ft Nicole...

The JTrain Podcast ·

2026/06/24

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

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00:30:08

Train Signage, Hosting A Friend's Birthday, and...

The JTrain Podcast ·

2026/06/23

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

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