The JTrain Podcast

Host: Jared Freid
Episode: My Boyfriend Won't Let Me Come To His Grandma's Shiva! Help! - MAILBAG MONDAY
Date: December 8, 2025

Episode Overview

This Mailbag Monday episode sees Jared Freid solo, answering listener emails about the everyday dilemmas of relationships, family, friendships, and post-grad life. With the comic’s signature blend of empathy, directness, and humor, he tackles problems ranging from dishwashing disputes to being excluded from a significant other's family event and the complexities of money among friends.

Key Discussion Points & Insights

1. Navigating Household Chores & Relationship Dynamics

Email Subject: Co-habitation Dishwashing Drama
Timestamp: 06:39 – 15:45

• Situation: A woman in her 30s, recently moved in with her boyfriend, finds herself at odds over washing dishes in their dishwasher-less apartment.
• Dilemma: He insists on immediate dishwashing; she prefers to let dishes soak and do them later. This difference leads to him doing the dishes more often, causing conflict and feelings of blame.

Jared’s Core Advice:

• Acknowledge Personality, Not Morality: Jared urges listeners to separate “neatness” from a sense of moral hierarchy.

  “The problem is with neat and tidy Guy and Sloppy Sarah, you feel like you’re morally beneath him. That’s the problem with neat and tidy person. They make it a moral argument, a moral hierarchy...”
  — (11:20)

• Don’t Keep Score: Focus on division of labor by preference, not strictly equal splits:

  “You’re barking up the wrong tree. I need him to be more flexible on dishes. That ain’t going to happen. You’re dating a dish guy. Let him be a dish guy.”
  — (12:25)

• Find Your Own “Thing”: Suggests trading responsibilities: if he’s "dish guy," she could choose and own another regular household task that matters more to her.

  “Let him own the space, and then let’s think of what space you could own. Maybe it’s making the bed, maybe it’s laundry folding that you want to be able to get done.”
  — (13:45)

• Takeaway: Assign chores by whose standards can’t bend, not by a 50/50 tally.

2. Being Excluded from Significant Family Events

Email Subject: “My boyfriend won’t let me come to his grandma’s Shiva! Help!”
Timestamp: 17:23 – 27:26

• Situation: A listener’s boyfriend of four months (eventually a year+) refuses to let her attend family shivas for his grandparents, as he feels it’s not the right way for her to meet his family.
• Emotional Result: She feels hurt, confused, embarrassed, and struggles to explain the situation to friends and family.

Jared’s Core Advice:

• Family Events Are Relationship Litmus Tests:

  “A death is a relationship pop quiz... how do I fit into you grieving with your family and me grieving with you and this whole greater universe that is called us?”
  — (20:40)

• Don’t Outsource Your Hurt:

  “How am I going to be in a relationship with someone who doesn’t want me there for them when their grandparent passes away and hasn’t introduced me to their family that… we’re seven months in. That’s the question.”
  — (23:32)

• Communicate Directly:

  “You’re using all these rationalizations to have feelings. You’re allowed to have feelings. I was let… just say it. I was let down when you didn’t have me at your grandparents’ Shiva.”
  — (25:03)

• Clarify Relationship Expectations: Rather than focus on the event, ask bigger questions: “What are we doing here? How come I’m not meeting your family after so long?”
• Takeaway: Don’t ignore red flags. If someone consistently compartmentalizes you out of life milestones, confront it honestly and consider your boundaries.

3. Money, Privilege, and Friendship

Email Subject: Med school, student loans, and the Venmo stingy friend
Timestamp: 29:14 – 34:30

• Situation: Medical student with significant debt is irked by a friend whose parents cover all expenses. The friend is extremely precise (even “cheap”) about splitting costs and sometimes fails to pay her back for shared expenses.
• Dilemma: Is it wrong to be upset about the exactness and occasional lack of repayment?

Jared’s Core Advice:

• Don’t Sweat Exactness:

  “If it’s 26.42 and they send you half… that is what she owes you. I think you gotta leave that complaint at the door. It’s a personality trait…”
  — (30:44)

• When to Draw the Line: When someone fails to pay at all, it’s fair to address it directly, focusing on your situation, not theirs.

  “Hey, I consider you a friend. It really bothers me when you don’t Venmo me back because money in my life is pretty scarce…”
  — (32:20)

• On Privilege:

  “Privilege is a very difficult thing to get across to someone else… Everyone explains their life in a way where they don’t have it easy.”
  — (34:12)

• Parallel with Comedy Crowd: Jared compares repeated warnings to audience members filming at his shows to giving friends chances:

  “Some people are not going to hear you. ...I would give them the benefit of the doubt. If they don’t take it, they don’t want to listen to you.”

• Takeaway: Communicate your needs. If a friend repeatedly ignores your situation, reconsider the friendship.

Notable Quotes & Memorable Moments

• On Chore Disagreements:
  “You’re dating a dish guy. Let him be a dish guy.” — Jared, (12:25)
• On Relationship Pop-Quizzes:
  “Beware of birthdays, holidays, death and Valentine’s Day and global pandemics. They will all tell you what you are to the other person or how the other person sees the relationship.” — Jared, (19:05)
• On Emotional Honesty:
  “You’re using all these rationalizations to have feelings. You’re allowed to have feelings.” — Jared, (25:00)
• On Money and Privilege in Friendships:
  “Comparison is the thief of joy. It’s a saying for a reason, because it’s very true. It is stealing your joy…” — Jared, (30:44)
• On Drawing Boundaries:
  “If they can’t respect the story you’ve just told them about you, they’re not really your friend.” — Jared, (34:12)

Important Segment Timestamps

• Intro & Banter – 00:20–04:55
• Household Chores / Dish Routine Advice – 06:39–15:45
• Sponsor (Nutrafol) – 15:45–17:23
• The Shiva Exclusion Email – 17:23–27:26
• Sponsor (Hero Bread) – 27:26–29:14
• Money & Friendship Dynamics Email – 29:14–34:30

Episode Style & Tone

Jared’s tone throughout is candid, playful, and empathetic, with a touch of tough love. He demonstrates a keen ear for the real root of each listener’s problem and delivers unfiltered advice with comic timing and memorable analogies.

Conclusion

If you want honest advice that’s both sharp and supportive, with plenty of laughs, this episode delivers. Jared’s key message: don’t be afraid to communicate your real feelings directly—whether it’s about chores, relationships, or money. And remember, sometimes the hard truth is the greatest gift a friend (or a podcaster) can give.