My Boyfriend Won't Spend Christmas With Me! Help!  - MONDAY MAILBAG episode artwork

EPISODE · Dec 22, 2025 · 31 MIN

My Boyfriend Won't Spend Christmas With Me! Help! - MONDAY MAILBAG

from The JTrain Podcast

Mailbag Monday has Jared holding the line through the holidays and diving into three juicy listener dilemmas. He cheers a fifth date move that involves designing a full on comedy show invite, reminding daters there’s no “too much” when you’re simply acting on your feelings. Then he tackles a tougher one: a two and a half year relationship stalled by a Christmas shutdown, explaining why holidays are sneaky relationship litmus tests and why this deserves a real sit down conversation. Finally, he breaks down a rom com adjacent crush on a taken guy, separating intuition from delusion and explaining why flirting from a relationship is its own dangerous vibe. It’s classic Jared, empathetic, blunt, and oddly comforting when dating gets messy.Jared is on tour! 👉 jaredfreid.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co Download the DraftKings Casino app now & enter code FEATHER for 500 FREE spins @ https://www.draftkings.com/mobileapps  

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My Boyfriend Won't Spend Christmas With Me! Help! - MONDAY MAILBAG

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