Podcast Summary: “What Happens When a Grandparent Won't Say No? Plus: Friends Who Are Difficult Diners”

Since You Asked with Lori Gottlieb and Gretchen Rubin | Lemonada Media
Date: November 18, 2025

Episode Overview

This episode of "Since You Asked" with Gretchen Rubin and Lori Gottlieb tackles dilemmas involving overindulgent grandparents and the challenges of dealing with difficult diner friends. The hosts address real listener questions, discuss group dynamics in recreational teams, and share community responses to tricky social scenarios, blending practical wisdom and humor.

Key Discussion Points & Insights

1. Listener Follow-Ups on Previous Advice

• Husband’s Family Lodging Preferences (02:26–04:29):
  A listener updates the hosts on how previous podcast advice helped her understand her husband's need for privacy during parental visits. This led to better communication and compromise in her marriage.
  • “One of the main things for my husband is that he wanted to feel understood... Although he does love my family, the comments from Mandy [Patinkin] resonated with both him and I…” – Listener Hannah (02:48)
• Handling Snappiness in Relationships (04:52–05:42):
  Another listener suggests using “memento mori” (awareness of mortality) as a tool to curb impatience and snappiness with loved ones.

Notable Quote:
“How would I be treating this person if today was our last day on Earth together?... It almost instantly makes me shift my behavior.”
— Listener Hannah (04:52)

2. Navigating Group Dynamics: Sports Team Scheduling Conflict

Main Listener Question (06:27–13:14)

A listener co-founded a recreational sports team. Her co-founder now wants the group to change their practice night to accommodate her kids’ schedules, potentially at the group's expense. Should one person’s preferences (even a co-founder) dictate the group’s activities?

Hosts’ Advice:

• Acknowledge Unreasonableness: It's not reasonable for one member to expect the entire group to adjust for her situation (08:08–08:28).
• Friendship vs. Policy: Friendship complicates impartial decision-making, but group needs come first (08:28–09:23).
• Set Clear Policies: Suggest stating openly: “This is the night that works for the team and coach. If individual circumstances change, you're welcome to rejoin when able” (11:24–12:12).
• Don’t “Do Her Bidding”: The co-founder can pose her request directly to the group instead of making the caller act as mediator (09:51–10:26).

Notable Quote:
“Groups really do best when the expectations and policies are clear, even in casual groups like this.”
— Lori Gottlieb (11:24)

Memorable Moment:
Gretchen notes that many people "kind of want somebody else to do all the work" of schedule wrangling, and how such burden often falls to organizers (09:23).

3. Wisdom of Crowds: Difficult Friends at Restaurants (13:35–19:14)

Poll Results:

• Leave a huge tip to compensate: 46%
• Gently try to get your friend to chill: 28%
• Ignore: 19%
• Apologize to the server in front of friend: 7% (14:04)

Listener Opinions:

• Some have accepted their friends’ quirks, as long as they remain polite (Amanda's story of "extra hot lattes and 20 lemon slices" – 14:27).
• Teasing or humorous approaches can ease tension but risk sounding passive-aggressive (Jenny Bell’s “not too French” fries joke – 15:00).
• Awareness and empathy are crucial; food allergies and legitimate dietary needs should always be taken seriously (Aaron’s experience as a diabetic – 15:55–16:42).
• Impatient, rude, or excessive behavior, however, may signal deeper underlying issues, per both hosts and some listeners (18:04–19:14).

Notable Quote:
“How a person treats service professionals tells you everything you need to know about them as a person.”
— Listener Kelly (15:42)

Host Reflection:
“If they’re doing it every single time, then clearly it isn’t the food. This is the person’s pattern of behavior.”
— Gretchen Rubin (19:11)

4. Main Segment: Overindulgent Grandma – Where’s the Line? (23:24–32:53)

Listener Tanya’s Dilemma (23:34–25:36)

Tanya describes her mother-in-law as loving but unable to say "no" to the grandkids, leading them to exploit her generosity—skipping chores, repeatedly getting replacement toys, and even pitting grandmother against parents.

Discussion Highlights

• “Grandparent Boundaries”:

  • Grandparents have a unique and cherished role, and some flexibility is healthy; "kids do understand different rules at different houses" (26:07–26:38).
  • True manipulation or long-term harm is unlikely if parents maintain structure at home (26:38–27:05).

• Dealing With Grandparent Overindulgence:

  • Draw the line where the grandparent’s actions directly affect your own household or undermine your authority (28:04, 32:07).
  • Assign “special” activities to each household: e.g., “Miniature golf is our thing—please leave that for us” (28:04–28:16).
  • If children run to grandma for “rescue,” reinforce with both child and grandma that parental decisions are final. Repetition of this response trains both parties (27:05–28:04).

• Perspective & Research:

  • Highlight the fleeting nature of this stage and the positive, buffer-like impact of grandparent relationships on children's mental health (28:37–28:58).

Notable Quotes:

• “Be grateful that the grandchildren want to spend this time with their grandmother… Even if it feels a little exploitative, it’s wonderful to have these close ties.”
  — Gretchen Rubin (28:16)
• “Kids feel safe with structure and limits and consequences. You guys aren’t the bad guys. They crave this sense of containment.”
  — Lori Gottlieb (31:10)

• Enabling vs. Overindulgence:
  • Lori clarifies: "Enabling" is supporting genuinely destructive behavior; this scenario is best categorized as “overindulgence” (29:38–30:49).
  • Overindulgence from a grandparent is generally harmless, provided kids are learning boundaries elsewhere.

Actionable Advice (31:01–32:35)

• Stay focused on maintaining clear expectations at home.
• Request that grandma not intervene in parent-child disputes or certain family traditions.
• Don’t overreact; cherish this special intergenerational connection.

Host Wisdom:
“For the things that she loves doing and she wants to do, even if you think they’re excessive, why intervene if she wants to?”
— Gretchen Rubin (32:07)

5. Bonus Listener Segment: “Post-Event Blues” (36:46–39:53)

• A listener’s question about post-wedding depression leads to a group reflection on the “crash” after big accomplishments—marathons, holidays, sending kids to college.
• Listeners emphasize this is normal and share tips for planning something new to avoid the “letdown.”

Notable Quote:
“There is so much anticipation… You think not only is it going to be positive when it happens, but the positivity is going to last.”
— Lori Gottlieb (39:33)

Most Memorable Quotes

• “Groups really do best when the expectations and policies are clear, even in casual groups like this.” — Lori Gottlieb (11:24)
• “How a person treats service professionals tells you everything you need to know about them as a person.” — Listener Kelly (15:42)
• “Be grateful that the grandchildren want to spend this time with their grandmother. Even if it feels a little exploitative, it’s wonderful to have these close ties.” — Gretchen Rubin (28:16)
• “Kids feel safe with structure and limits and consequences.... They crave this sense of containment.” — Lori Gottlieb (31:10)

Timestamps of Important Segments

• 02:26: Family lodging boundary discussion (Listener follow-up)
• 06:27: Navigating co-founder scheduling conflicts in groups
• 13:35: Survey and listener input—difficult diners at restaurants
• 23:34: Overindulgent grandparent dilemma and advice
• 36:46: “Post-wedding blues” and post-event letdown stories

Tone & Style

Lori and Gretchen maintain an empathetic, conversational tone throughout—balancing humor, research-based insights, and personal experience. They encourage listeners to reflect with compassion on both themselves and others, and to seek happy mediums in everyday dilemmas.

Next Episode Teaser

The hosts invite discussion on a delicate issue:
How do you tell a friend their Botox/fillers are getting out of hand (or do you stay silent)?

This episode is rich in real-life dilemmas, practical frameworks, and compassionate advice—an engaging listen for anyone navigating family, friendship, and group dynamics.