• 44 minutes 25 seconds
    Can AI Replace Human Love? ft. Bridget Todd - CHIT CHAT WEDNESDAY

    Jared is joined by author and tech journalist Bridget Todd to talk about her new book, Love at First Prompt! They also discuss👇

    • AI girlfriends and digital intimacy
    • The future of dating apps and AI
    • Can AI actually improve relationships?
    • They play AI vs. Human -What’s a Better 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 and get 20% off Lean weight loss supplement with code JTRAIN at https://takelean.com 

    Go to http://cometeer.com/JTRAIN for $20 off your order

    29 July 2026, 4:00 am
  • 41 minutes 43 seconds
    First Birthday Madness, Hotel Soap Fails & Why Video Podcasts?! - TICKED OFF TUESDAY

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

    • Is a 1st birthday party with 56 ppl way over the top?
    • Why are hotels still using bar soap?
    • Did podcasts get worse when they added video?
    • Why did I have to wait after a stranger paid for my groceries?


    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

    28 July 2026, 4:00 am
  • 42 minutes 22 seconds
    Who Should Pay for an Engagement Ring? Me or My BF?! - MONDAY MAILBAG

    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.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 

    27 July 2026, 4:00 am
  • 39 minutes 48 seconds
    Matt Damon Mix Up, BBC Commentator Blunder and JLo's Birthday Photos - POP CULTURE THURSDAY

    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 final
    • Jennifer Lopez bathtub birthday photos before turning 57
    • BBC commentator confuses Pharrell with A$AP Rocky at World Cup final
    • Sammy Sheen says Charlie Sheen has not given her money and credits OnlyFans for her success
    • Megan Fox claps back after critics call her lingerie photos embarrassing


    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!

    Go to https://cometeer.com/JTRAIN for $20 off your order!

    Support the show and update your outdoor space @ http://Wayfair.com

    23 July 2026, 4:00 am
  • 45 minutes
    Gen X vs Millennials In Love ft Des Bishop - CHIT CHAT WEDNESDAY

    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 relationships
    • Why nostalgia is so powerful
    • Now or Then game: old vs new life choices


    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!

    Go to https://cometeer.com/JTRAIN for $20 off your order!

    Support the show and update your outdoor space @ http://Wayfair.com

    22 July 2026, 4:00 am
  • 27 minutes 58 seconds
    People Singing At Fitness Class, Taking A Tour Of Someone's Home, and Airport Behavior - TICKED OFF TUESDAY

    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.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 


    The Korean skincare brand everyone is talking about. Jtrain fans get 20% off their entire order by using code JTRAIN at http://jiyuskin.com/ #JiYu #ad

    21 July 2026, 4:00 am
  • 27 minutes 55 seconds
    Do Men Care If I'm A Sweaty Date? - MONDAY MAILBAG

    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 child
    • I'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.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 


    The Korean skincare brand everyone is talking about. Jtrain fans get 20% off their entire order by using code JTRAIN at http://jiyuskin.com/ #JiYu #ad

    20 July 2026, 4:00 am
  • 43 minutes 57 seconds
    Arianna Grande's New Boyfriend, Page 6 Hates Rachel Ray, and Taylor Swift's New Dog - POP CULTURE THURSDAY

    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 week
    • Ariana Grande reunites with ex, Ricky Alvarez
    • Tom Segura and Christina Pazsitzky split
    • Rachel Ray sparks new health concerns
    • Taylor Swift and Travis Kelce's secret pet dog revealed!


    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!

    16 July 2026, 4:00 am
  • 44 minutes 50 seconds
    Why I Posted My Crying Clip ft Eric Neumann- CHIT CHAT WEDNESDAY

    Comedian Eric Neumann joins Jared to talk about his new special Call Your Mom, watch it today! They talk👇

    • Calling his mom live on stage
    • Getting notes from Ray Romano & Judd Apatow
    • Viral Knicks crying video
    • They play: Would You Cry?


    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!

    15 July 2026, 4:00 am
  • 35 minutes 40 seconds
    Sound off for the World Cup, Packing Up Leftovers, and Canvassers- TICKED OFF TUESDAY

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

    • Apartment canvassers have gone too far
    • Tiny airport bathroom stalls and suitcase struggles
    • Husband books an expensive vacation without asking
    • Are restaurants making you pack your own leftovers?


    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!

    Find & instantly book doctors appointments with ZocDoc @ http://ZocDoc.com/JTRAIN 

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

    14 July 2026, 4:00 am
  • 33 minutes 14 seconds
    Why Do My Hinge Matches Never Ask Questions? - MONDAY MAILBAG

    It’s Mailbag Monday, and Jared is answering listener emails and giving advice on real life problems👇 

    • Hinge matches that never ask questions back
    • Warning a coworker about a possible performance review
    • Dating again after losing a sibling, and when to share it


    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!

    Find &  instantly book doctors appointments with ZocDoc @ http://ZocDoc.com/JTRAIN 

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

    13 July 2026, 4:00 am
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