• Taylor And Travis Have 20 Minute Vows, James Taylor Doesn't Attend, and Harry Styles Flashes 90k People - POP CULTURE THURSDAY
    Jul 9 2026

    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 vows
    • Harry Styles' on stage wardrobe malfunction
    • Leonardo 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 bash
    • James Taylor turns down Taylor and Travis' wedding invitation
    • Zendaya wears Eiffel Tower themed headpiece at The Odyssey premiere



    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!

    • Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/JTRAIN #rulapod #ad
    • Go to cometeer.com/JTRAIN for $20 off your order!


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    36 mins
  • I Got Hit By a Bus! ft Ryan Hamilton - CHIT CHAT WEDNESDAY
    Jul 8 2026

    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 anxiety
    • Turning a bus accident into comedy
    • Writing a personal comedy special
    • They play “Which Hits Worse?”


    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!

    • Connect with quality therapists & mental health experts who specialize in you at https://www.rula.com/JTRAIN #rulapod #ad
    • Go to cometeer.com/JTRAIN for $20 off your order!
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    42 mins
  • The 5 Worst Menu Items, Bridal Showers, and Upgrade Certificates - TICKED OFF TUESDAY
    Jul 7 2026

    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.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 code FEATHER at https://www.hero.co

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    33 mins
  • Met a Guy at a Bar and He Ghosted! Why Waste My Time? - MONDAY MAILBAG
    Jul 6 2026

    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.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 code FEATHER at https://www.hero.co

    Show More Show Less
    34 mins
  • Taylor Swift Wedding Timeline, Menu, and Travis Kelce's Pre-Wedding Routine - POP CULTURE THURSDAY
    Jul 2 2026

    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 plans
    • Taylor Swift wedding menu revealed
    • MSG lockdown for Taylor Swift wedding
    • Kyle Cooke and Ava Dash romance rumors
    • Rob Kardashian's rare family appearance


    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!

    For free shipping on your order & 365-day returns go to https://www.Quince.com/JTRAIN



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    28 mins
  • The Reality of Joining Instagram Later in Life! ft Emmy Blotnick - CHIT CHAT WEDNESDAY
    Jul 1 2026

    Comedian Emmy Blotnick joins Jared to talk about her new special, What's Her Secret? They talk👇

    • Social media vs. stand-up comedy
    • Sephora, skincare, and beauty culture
    • Japan travel and culture shocks
    • Kevin Hart roast behind the scenes
    • Commercial jingles and Skyrizi ads
    • They play: Would You Watch?


    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!

    For free shipping on your order & 365-day returns, go to https://www.Quince.com/JTRAIN

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    46 mins
  • Facebook Marketplace, People with Fake Allergies, & Online Clothing with Only ONE Picture - TICKED OFF TUESDAY
    Jun 30 2026

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

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    36 mins
  • How Do I Keep The Momentum Going With A Guy During My Summer Travel? - MONDAY MAILBAG
    Jun 29 2026

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

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    40 mins