The JTrain Podcast

Host: Jared Freid

Episode Title: I'm Going To My Boyfriend's For Thanksgiving and His Mom Is Insulted I Asked To Cook! Help! - MAILBAG MONDAY
Date: November 24, 2025

Episode Overview

In this Mailbag Monday episode, comedian Jared Freid answers three listener emails ranging from navigating early relationship and career woes, to airport lounge etiquette with friends, and tackling tricky Thanksgiving family dynamics. The episode is loaded with Jared’s signature humor, candid takes, and actionable advice—he pulls no punches, especially when addressing Italian mothers and stuffing duels.

Key Discussion Points & Insights

1. Navigating Early Relationship ‘Reveal’ & Financial Imbalances

• (04:31–19:00)
• Listener’s question: She’s been dating a guy for a month (five dates), wants to know how/when to say she's not seeing others, and how to handle paying for dinners since he was recently laid off (she may be laid off soon too).
• Jared’s advice:
  • The “reveal” isn’t a ‘What are we?’ talk, but a straightforward statement:

    “I am having fun, I have deleted the apps, I would like to explore what this is with you. And then—the secret to the reveal: shutting the fuck up.” (06:00)

  • Most people aren’t master manipulators; assume decency.
  • Revealing you’re focused on them is a strong, honest move—don’t overthink if he’ll run.
  • On paying for dates:
    • Don’t mix issues; solidify relationship direction first, then discuss logistics.
    • If you’re now in a relationship or moving towards “we,” negotiate openly:

      “How have you envisioned handling this?” (17:20)

    • It’s about moving from “I” to “we.”
• Jared’s recurring theme:

  “Let’s stop thinking of these people we’re dating as master manipulators... Most people are fine people. Not great, not bad. Just fine.” (08:24)

2. Airport Lounge Etiquette for Groups vs. Solo Travel

• (22:05–33:30)
• Listener’s question: Should you ditch friends and family without lounge access? Should you pay for their guest fee?
• Jared’s rules:
  • Once you’re at the airport, you’re individuals until after security—it's not summer camp.
  • If traveling with one friend, bring them in as a guest, split the cost—“I take the decision out of their hands. I’m bringing you with me.” (24:09)
  • More than one friend:
    • Depends on time, who the friends are, and if it’s worth the cost/risk of becoming subject to post-trip gossip.

    • "You are now risking being the topic of a shit-talking conversation. They will talk badly about you. They will say, 'I can't believe they need that that much.'" (27:25)

  • Don’t be shocked not everyone has lounge access—people travel differently.
  • Group travel requires more consideration, like eating with others instead of solo mode.
  • Anecdote on plane boarding:

    "There is this subtle adjustment...going from alone traveler to group traveler where you have to act a little bit more appropriate than you would alone..." (32:15)

3. Thanksgiving Showdown: Challenging an Italian Matriarch

• (35:00–51:45)
• Listener’s dilemma: She offered to bring her “famous cornbread stuffing” to her boyfriend Luca’s Thanksgiving (his mom is the family’s legendary Italian cook). The mom had a “visceral reaction” and now there’s a stuffing standoff.
• Jared’s take:
  • Hilariously blunt—this was a major misstep:

    “You come in to an Italian mother’s home on a cooking holiday, hat in hand. Whatever I can do. Oh my god, you’re unbelievable. You don’t walk in to Nona’s big day and go, well check this out, I got my famous stuff. No. Too cocky, too confident.” (36:40)

  • Now it’s a high-pressure stuffing-off; social faux pas has put the listener in a tough spot.
  • Advice is clear:

    “You better make a stuffing that is so good that mama rigatoni tastes it, and all she wants to do is hate it, and she goes, ‘Yeah, it’s okay,’ while everyone else says, ‘Come on, it’s really good!’” (48:25)

  • Bring a massive amount—“the best you’ve ever made.”
  • Why this is so fraught:

    “She feels personal fulfillment from feeding the family...then you waltz in ... and you start saying, well, I make a pretty good stuffing too. And that’s you saying, I’m a better caregiver than you, Mama.” (49:30)

  • Even if a mistake, now the only option is to absolutely blow them away or risk utter family legend humiliation.
• Notable Memorable Moment:

  “It is time. To stuffing. It is time, and you got to bring a lot!” (50:30)

Notable Quotes

• On the ‘reveal’ (dating apps):

  “I only give advice that would work on me…Do I have this information about someone…and still go on living on a different page than them? That would be uncomfortable…” – Jared (07:15)

• On airport lounge etiquette:

  “When I get to the airport with other people, before security, we all go on our own... this is not a school trip.” – Jared (23:30)

• On stuffing diplomacy:

  “This is where I do my business. This is where the JCU comes in clutch.” – Jared (35:40)
  “You have gotten too...we’ve all done it. We’ve all gotten a little too cocky. We’ve all thought, everyone loves me. Of course I can make a few jokes. No, you can’t. You’re not in this family.” (43:30) “It’s time to show what all this bragging was all about. Time to stuffing, it is time to stuff it!” (48:55)

Timestamps for Important Segments

• Mailbag Monday Intro & Show Setup: 00:00–04:00
• Dating 'reveal' & job layoffs: 04:31–19:00
• Ad read (skipped)
• Airport lounge question: 22:05–33:30
• Epic Thanksgiving stuffing dilemma: 35:00–51:45

Episode Tone & Style

Jared keeps things honest, self-deprecating, and fun. He isn’t afraid to call out risky social moves or poke fun at common anxieties, but always lands on practical, clear-eyed solutions. The energy is conversational, brisk, and loaded with comedic exaggeration, especially during the stuffing showdown.

Summary for New Listeners

Whether you’re facing awkward new relationship territory, traveling with less-prepared friends, or running afoul of a beloved family cook, this Mailbag Monday gives you the real talk and comic relief you need. Jared’s take is consistently bold with memorable metaphors (and Italian mama nicknames), turning small social missteps into epic teachable moments.

If you want to know whether to walk boldly into Thanksgiving with your cornbread stuffing, listen to this episode—or at least take Jared's advice: bring it, and make it legendary.