Podcast Summary: "How Do You Handle a Conversational One-Upper? Plus: Elizabeth Gilbert Has a Question!"

Since You Asked with Lori Gottlieb and Gretchen Rubin
Date: October 28, 2025
Host: Lemonada Media

Overview

In this rich and relatable episode, Lori Gottlieb and Gretchen Rubin field listener updates and common dilemmas around connection, communication, and boundaries—just in time for the busy holiday season. The episode tackles topics like feeling left out in family gift-giving, the joys and annoyances of frequent texts, how to handle a “conversational one-upper,” and ends with special guest Elizabeth Gilbert asking the pair for advice on managing anxiety about decisions made by loved ones.

Key Discussion Points & Insights

1. Listener Updates: Family Secrets and Post-Wedding Blues

• Update #1: Sister’s dilemma on revealing egg donor conception to her niece (03:12).
  • The update underscores the complexity of family secrets and the importance of seeking support, especially through therapy.
  • Gretchen: "It's a great idea for the sister to see a therapist to clarify her feelings and get support in making this big step to share that truth." (04:01)
• Update #2: Thessaly’s “post-wedding depression” (04:21).
  • Thessaly credits open communication with her husband as vital to their transition, recognizing her need for space and how it isn’t a reflection on him.
  • Lori: "She was very clear that this is something I'm experiencing and I'm asking for your support, not you are the problem..." (08:12)

2. Holiday Dilemma: Left Out of Family Gift-Giving (09:59)

A listener, Leanne, feels excluded from her nieces’ lives because her brother discourages gift-giving in favor of impersonal book vouchers.

Main Insights:

• Gifts as Connection:
  • Lori frames the dilemma as being less about presents and more about yearning for closeness:
    "Giving a gift is as much for the giver as it is for the receiver...what she's seeking is for the nieces to think... fondly of the aunt and keep her in mind." (10:31)
• Family Values Differ:
  • Gretchen: "Some people just don't want things...It may be that he's not being deliberately thoughtless; it's just not what they value as a family." (11:08)
• Love Languages Matter:
  • Discussion of "The Five Love Languages" (12:45) and their role in mismatched expectations.
• Practical Connection Tips:
  • Gretchen suggests finding a collection (e.g., ornaments) or communicating directly with the nieces via tech (15:45).
  • Lori: "Just ask the kids yourself if you want to have a closer relationship..." (15:58)

3. Poll: Are Midday Texts Annoying or Connecting? (16:42)

Perspectives Shared:

• Gretchen enjoys frequent 1-on-1 or small group texts (17:21).
• Lori finds frequent texts distracting during the day, unless it's from her son (19:20).
• Listener Poll Result:
  • 88% enjoy frequent texts, 12% find them annoying
• Notable Quotes:
  • "I like a free, no pressure brain exchange." – Amy (18:43)
  • "Texting isn't connection, it's clutter." – Kim (21:53)
• Tips:
  • Use delayed send, mute notifications, and check texts during set times (20:03).

4. Main Dilemma: The Conversational One-Upper (26:34)

Listener's Problem:

A listener feels diminished by a friend who constantly “one-ups” any story or achievement.

Hosts’ Advice:

• Origin of One-Upping:
  • Lori: "Usually it comes from a place of insecurity...it's probably related to feeling ignored or dismissed...she doesn't realize she's doing this." (27:33)
• Strategies to Cope:
  • Set Boundaries in Real Time:
    • Lori: "You can say, ‘Right now we're talking about me, and then I want to hear about you.’" (28:15)
  • Use Humor to Diffuse:
    • Gretchen suggests gently raising the issue with humor, if possible: "Sometimes if you can achieve that light tone, it can make it much easier..." (28:37)
  • Address Directly with Compassion:
    • Lori: "You can just say, hey, I notice that when I'm telling you something about myself, I get interrupted... I'm sure you don't mean it." (29:13)
  • Ignore the Topping ("Extinguishing the Behavior"):
    • Try continuing your story without reacting to the one-upping to see if it extinguishes the behavior (30:23).
• Deciding the Friendship's Value:
  • Gretchen: "This is the friend we got. Is the good stuff worth it in terms of what we're getting with the friendship?" (31:05)
  • Lori: "Please don’t ghost your friend without saying what the issue is. It’s really respectful to be able to say to somebody, here’s what the issue is." (31:31)

5. Special Segment: Elizabeth Gilbert Asks for Advice (36:14)

Elizabeth Gilbert’s Question (Writer of Eat, Pray, Love):

"How do you guys handle the anxiety of worrying about friends or family members who are acting out or behaving in ways that seem dangerous or self-defeating? Asking for a codependent friend..." (36:14)

Hosts’ Response:

• Letting Go of Control:
  • Lori: "We can get overly invested and have this illusion of control over what our friends do. Sometimes it's helpful to step back...you can share your thoughts, not by saying, 'Hey, you're making a huge mistake,' but just to observe..." (37:47)
• A Stumble May Prevent a Fall:
  • Gretchen: "Sometimes when people make a mistake, it's actually a mistake that will save them from making a much bigger mistake later..." (37:47)
• Help-Rejecting Complainers:
  • Some people don’t want solutions, just validation for their woes. Gretchen: "If you offer any advice, they reject it. But if you just say, 'Well, what are you planning to do?' it ends that." (40:33)
• Practical Tips:
  • Schedule time to worry to avoid being consumed by anxiety (41:31).
  • Lori: "You can care about a friend, but you don't need to take over their anxiety." (42:12)

Notable Quotes & Memorable Moments

• On Vulnerability in Marriage:
  • Thessaly: "He lets me go to sleep first and then waits 20 to 30 minutes for me to fall asleep before quietly coming into the room to go to bed." (05:10-05:20)
• On Navigating Differences in Family Traditions:
  • Gretchen: "Maybe you could find something like that [a collection], where it would satisfy your desire to give that special gift and would be exciting for the girls to collect..." (15:45)
• On Feedback with Friends:
  • Gretchen: "The true way to care for people is to give them constructive criticism." referencing Kim Scott’s "Radical Candor" (32:48)

Timestamps for Key Segments

• Listener Update on Family Secret: 03:12 – 04:01
• Listener Update on Marriage Transition: 04:21 – 08:12
• Holiday Gift-Giving Dilemma: 09:59 – 16:24
• Texting Poll & Discussion: 16:42 – 22:32
• Conversational One-Upper Dilemma: 26:34 – 33:21
• Elizabeth Gilbert’s Question & Discussion: 36:14 – 42:44

Overall Tone & Takeaways

In true "Since You Asked" style, Lori and Gretchen blend lightness, warmth, and practical wisdom—never shying from honesty, but always centering kindness and clarity in difficult conversations. They encourage listeners to find what’s really at the core of their dilemmas, communicate directly (but gently), and remember that everyone has a different way of giving and receiving love.

Next Week's Question Teaser

A listener struggles with an overly-sensitive niece who tends to cry and dominate family gatherings—questioning how best to manage emotional outbursts without derailing celebrations. Listeners are invited to weigh in for next week's show.

Episode Purpose:
To validate and explore everyday emotional challenges, helping listeners nurture more thoughtful connections—with family, friends, and themselves—through candid dialogue, empathy, and actionable advice.