• Why Are Men's Dating Profiles So Bad? - MONDAY MAILBAG
    Mar 23 2026

    It’s a Mailbag Monday! Jared is answering your emails with honest, no-BS dating and relationship advice. Three listeners write in with real situations like 👇

    • Dating apps frustration and how to rethink bad matches
    • Meeting the parents and overthinking family dynamics
    • Low effort dating behavior and when to walk away


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    34 mins
  • The Bachelorette Allegations, NYC Nepo Baby Bat Mitzvahs, and Old Rappers - POP CULTURE THURSDAY
    Mar 19 2026

    It's Pop Culture Thursday! Jared is diving into this week's wild celebrity stories👇

    • Rebecca Hessel Cohen hosts $500K Plaza bat mitzvah for daughter Scarlett
    • Jennifer & Omer Horev throw luxe NYC-themed bat mitzvah for daughter Emma in Florida
    • Taylor Frankie Paul addresses alleged domestic violence ahead of The Bachelorette premiere
    • Nicholas Holt & Brianna Holly respond to criticism over Vanity Fair Oscar party dress

    And more!


    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


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    41 mins
  • Priyanka Grandhi - Why she went on Love Is Blind & Her History With Alex! - CHIT CHAT WEDNESDAY
    Mar 18 2026

    Chit Chat Wednesday with Priyanka Grandhi, Love Is Blind Season 10 cast member and recruiter in Austin. Priyanka joins Jared to talk 👇

    • Behind the scenes of Love Is Blind Season 10!

    • Ohio roots, Austin life

    • Men, vulnerability, and dating after Love is Blind

    • Alex and Ashley drama

    • Plus, they play Jared’s game, Love It Blind!


    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


    Get 20% off all mattresses PLUS an extra $50 off with code JTRAIN at http://Leesa.com

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    46 mins
  • Correcting Grammar Online, Late Hairstylists, and Tipping Police - TICKED OFF TUESDAY
    Mar 17 2026

    It’s Ticked Off Tuesday! Jared reacts to four everyday complaints that would annoy anyone!👇

    • Correcting grammar on a TikTok post

    • Overbooked flight drama and fighting for a travel voucher

    • Hair salon double booking and terrible customer service

    • Bakery gave the worst pumpkin bread slice

    • Bar tipping screen embarrassment and cash tip judgment



    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


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

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    34 mins
  • Did My Long Distance Fling End It? Interpret These Screenshots Please! - MONDAY MAILBAG
    Mar 16 2026

    It’s a Mailbag Monday! Jared answers listener emails with honest dating advice and real talk! Jared answers dating dilemmas like👇

    • Dating a great guy, but turned off by his unhealthy habits

    • Long-distance situationship confusion after a vague text reply - did we break up??

    • Is a privacy screen on your partner’s phone a red flag?


    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


    support the show, support the sponsors!

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

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    39 mins
  • Timothée Chalamet Hates Ballet, Joint Bachelor / Bachelorette Parties, and Tomi Lahren - POP CULTURE THURSDAY
    Mar 12 2026

    It's Pop Culture Thursday! Jared riffs on the wildest celebrity headlines of the week 👇

    • Timothée Chalamet vs Misty Copeland ballet drama
    • Kathie Lee Gifford calls out The View on Tomi Lahren’s podcast
    • Dak Prescott and Sarah Jane Ramos wedding canceled after cheating claims
    • NYC Spence School scandal tied to alumni Gwyneth Paltrow and Kerry Washington



    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


    support the show, support the sponsors!

    Get 40% off select Lola Blankets products at http://Lolablankets.com by using code JTRAIN at checkout. Experience the world’s #1 blanket with Lola Blankets.

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    34 mins
  • Best Apps For Date Night! ft. Marissa Mullen - CHIT CHAT WEDNESDAY
    Mar 11 2026

    CHIT CHAT WEDNESDAY is here & this week, Marissa Mullen joins to talk about her new cookbook, I’ll Bring the Apps, and how to host easy snacky parties with bites, bowls, and boards.

    • Marissa shares her move from Brooklyn to the Hudson Valley, building community with food
    • Her apps hosting method
    • Conversation on modern hosting, social connection, and simple appetizer recipes that make entertaining easier
    • They play “What App Would You Bring?”, choosing appetizers for different party scenarios



    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


    support the show, support the sponsors!

    Get 40% off select Lola Blankets products at http://Lolablankets.com by using code JTRAIN at checkout. Experience the world’s #1 blanket with Lola Blankets.


    Use code jtrain50off to get 50% off your first box, plus Free Breakfast for 1 year at http://FactorMeals.com/jtrain50off

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    49 mins
  • Checking In and Checking Out of the Hotel, Plus More Complaints! - TICKED OFF TUESDAY
    Mar 10 2026

    TICKED OFF TUESDAY is here. Jared vents and reacts to your petty complaints, travel rage, and everyday annoyances.

    • Gym shirts that guilt you before 7am
    • First class chaos after 16-hour travel
    • Teen boyfriend drowning in cologne
    • Target pickup hogs prime parking
    • Hotel check-in & check-out



    Jared is on tour! 👉 jaredfreid.com

    Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


    Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

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    39 mins