Since You Asked with Lori Gottlieb & Gretchen Rubin

Episode: Should You Call Out an Awkward Problem? Plus: Did We Follow Our Own Advice?
Date: January 20, 2026
Podcast Host: Lemonada Media

Episode Overview

This lively and candid episode kicks off Season Two of "Since You Asked," with therapists and advice experts Lori Gottlieb and Gretchen Rubin diving deep into one of the most delicate and universally relatable topics—how to compassionately address an awkward personal issue, specifically: telling a loved one they have bad breath. The hosts also reflect on holiday advice—whether they follow it themselves—and share listener responses to memorable dilemmas from last season.

Key Discussion Points & Insights

1. Grief and Season Two’s New Beginning

• Gretchen opens up about the recent loss of her father and how it has shifted her personal outlook.
  • [01:31] “I have sad news that my beloved father died. Our family was with him right at the end, which was a huge comfort to us.” — Gretchen Rubin
• Lori highlights the universality and complexities of grief, inviting listeners to share their own experiences.
• Both promise an upcoming, dedicated episode on dealing with loss.
  • “Loss is universal. We all experience loss, but it’s also so personal..." — Lori Gottlieb [02:13]

2. Listener Mailbag – Updates on Past Dilemmas

• The hosts revisit three listener questions from Season One that generated the most discussion:
  • Most life-changing advice received. Listeners’ stories and wisdom will continue to be featured in future episodes.
  • How to deal with a difficult friend in public settings.
  • Experiencing post-wedding blues—and how positive events may still produce post-event sadness.
    • “Sometimes there is this period of melancholy or disappointment or blues that comes after [good events].” — Gretchen Rubin [04:33]

Listener follow-up highlights:

• Monthly Gatherings: Consensus from listeners supports not changing group plans for one person’s schedule. [05:13]

• Botox Honesty: A listener shares that her friend dismissed her comment, and reinforces positive reinforcement over criticism. [05:52]

• Gift-Giving Aunts: Tangible vs. experience gifts spark frustration—and creative solutions, like gift cards or experience memberships, gain traction. [06:46]

  “I think people need to remember that the gift is for the recipient.” — Lori Gottlieb [08:11]

3. Main Dilemma: Should You Tell Someone About Bad Breath?

Listener Question from Ciara

[10:15]

• Ciara describes her close bond with her mom, but is distressed by her mother’s chronic bad breath and wants advice on broaching the subject compassionately.

Lori & Gretchen’s Insights

• Acknowledging the Awkwardness:

  • "There is something special about smell. It’s so intimate, it’s so sensitive." — Gretchen Rubin [11:08]

• Why It’s Important:

  • Not just about daughter/mother comfort—bad breath can affect all close relationships, and could indicate a deeper medical issue.
    • "This could also be a sign of a serious medical issue, especially if she takes care of her teeth." — Lori Gottlieb [11:30]

• Navigating the Conversation:

  • Frame feedback as coming from love, not criticism.
  • Use “I” statements, not direct accusations.
    • “We're so close, so I feel comfortable telling you something that is happening between us.” — Lori Gottlieb [12:40]
  • Acknowledge that the daughter would want to know, too, if the roles were reversed.
  • Normalize the issue—remind her it may be medical or medication-related, and not a hygiene failure.
    • "Bad breath can be medical or medication-related. It's not a hygiene failure." — Lori Gottlieb [14:15]
  • Choose the right moment, preferably not just before parting ways.

• Striking the Right Tone:

  • Deliver the message with lightness and avoid shaming language.
    • “You do want it to feel very loving... can you try to make it feel lighthearted, or not to strike that shameful tone?” — Gretchen Rubin [13:33]

4. Wisdom of Crowds: Who Should Deliver Difficult Truths?

[20:05]

• By coincidence, their recent social media poll mirrored Ciara’s dilemma: who would you want to tell you about a personal issue, a family member or a close friend?
  • Results: 67% would want a family member, 33% a friend.

Listener Quotes

• Amy Gray: "If a painful truth comes from a close friend and we stick together as friends after a painful truth is spoken, it means their intentions are pure." [21:25]
• Christine: “I’m the person who will tell you that painful truth. I may do it subtly and suggest that they get a mint or some gum.” [21:40]
• Laura: “I would want to be told, but be discreet and be kind.” [21:56]
• Kristy: "There is such a difference between benevolent and brutal honesty." [22:13]
• Marcie: “I'd like to think that it would result in a stronger friendship or relationship. Knowing our flaws…can help us build understanding and empathy." [22:19]
• Susie: “I’d prefer no one makes me too uncomfortable.” [22:45]
• Nicole: "Either and both should care enough and do the best they can to tell them in a way not to hurt them." [23:08]

Takeaway

• Kindness and good intent trump everything, but timing and delivery make all the difference.
  • “Benevolent honesty instead of brutal honesty.” — Lori Gottlieb [23:09]

5. Applying (or Ignoring) Good Advice During the Holidays

[28:30]

Hosts Reflect on Their Own Advice

• Gretchen’s Experience

  • Uses a friend’s advice: “Let it unfold” while grieving—no expectations, just acceptance.
    • “[I was told] just let it unfold…experiencing what I was experiencing and don’t judge it.” — Gretchen Rubin [29:23]
  • Lets go of sending holiday cards after much soul-searching—a tradition she admits wasn’t serving her.
    • "It was a big relief. It took a lot to make that final decision." — Gretchen Rubin [30:11]
  • Realizes she prefers scheduled plans over spontaneity, especially during stressful times.

• Lori’s Experience

  • Shifts her mindset from cramming all holiday visiting into one window; decides to spread visits throughout the year for more joy and less stress.
    • "Why does it have to be at this time? Why can't we go visit in March?" — Lori Gottlieb [31:39]
  • As a December birthday (like Gretchen), she insists that December birthdays shouldn’t be lost in the holiday shuffle.
    • “People with December birthdays deserve to get a birthday...don’t just combine these celebrations.” — Lori Gottlieb [32:38]

6. Next Episode’s Dilemma: Setting Boundaries in Communication

[34:39]

• Listener writes about a boyfriend’s need for constant texting, even when it feels exhausting or pointless.
• Lori and Gretchen invite listener input for next week’s discussion.

Notable Quotes & Memorable Moments

• “People do direct negative feelings towards people who tell them things they don’t want to hear. So it’s understandable that Ciara would be apprehensive.” — Gretchen Rubin [12:12]
• “You’re giving them a great gift...” — Lori Gottlieb, on telling someone a hard truth with kindness [24:07]
• “Let it unfold... Don’t judge it, don’t fight it, ride the wave.” — Gretchen Rubin [29:23]
• “Benevolent honesty instead of brutal honesty.” — Lori Gottlieb [23:09]

Timestamps for Key Segments

• [01:31] Grieving and family loss discussion
• [05:13] Listener updates on last season's advice dilemmas
• [10:15] Ciara’s question about how to mention her mom’s bad breath
• [11:08] The intimacy of addressing sensitive personal issues
• [12:40] Tips for approaching delicate conversations with loved ones
• [14:15] Medical normalization and choosing the right moment
• [20:05] Wisdom of Crowds: Who should break difficult news?
• [21:25] Listener comments + advice on honesty delivery
• [28:30] Hosts reflect on their own holiday advice and traditions
• [34:39] Teaser for next episode—texting boundaries in relationships

Listener Takeaway

This episode centers on some of life’s most awkward but necessary conversations, emphasizing honesty delivered with empathy. Lori and Gretchen model practical scripts for tough talks and reflect on how even experts sometimes struggle to follow their own advice. The power of kindness, intention, and timing are recurring themes, with plenty of wisdom from both hosts and listeners on navigating the messy and beautiful parts of being human.

For more advice, story follow-ups, or to submit your own question, visit sinceyouaskedpodcast.com.