Since You Asked with Lori Gottlieb and Gretchen Rubin

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

Oct 28, 2025

The hosts tackle the tricky situation of a friend who constantly one-ups conversations, exploring causes and offering humorous tactics to manage it. They also discuss family dynamics, from navigating impersonal gifts to addressing emotional boundaries. Bestselling author Elizabeth Gilbert asks how to cope with anxiety about loved ones' risky choices, leading to insightful strategies for relief. Listener updates on sensitive issues like egg donation and post-wedding blues add depth to the conversation.

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ANECDOTE

Post-Wedding Sadness Resolved With Talk

A listener described feeling post-wedding sadness and discovered she needed more alone time and reassurance.
Open communication with her patient husband, boundary-setting for alone time, and having fun helped her recover.

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ADVICE

Find Alternate Ways To Connect Remotely

If gifts aren't the family's preference, ask the brother how else you can connect with his children.
Use direct contact with the kids (FaceTime, calls, questions) or choose collectible, low-clutter gifts like ornaments.

insights

INSIGHT

Gifts Reflect Values, Not Rejection

Gift preferences reflect differing family values and love languages rather than deliberate rejection.
Assuming malice often obscures the underlying yearning for connection that the gift-giver feels.

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Elizabeth Gilbert Asks About Worrying Over Loved Ones

01:07 • 1min

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Update: Egg-Donor Secret Follow-Up

02:35 • 2min

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Update: Post-Wedding Sadness Resolved

04:11 • 5min

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How To Deepen Long-Distance Relationships Through Gifting

08:47 • 8min

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Do You Enjoy Getting Texts Throughout the Day?

How To Handle a Friend Who One-Ups Conversations

Elizabeth Gilbert: How To Stop Obsessing Over Others' Choices

35:57 • 7min

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Listener Question: How To Prevent a Relative's Tears at Gatherings

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Elizabeth Gilbert's 'All the Way to the River: Love, Loss, and Liberation' invites readers on a deeply personal journey through the complexities of human experience. Gilbert fearlessly explores the intricacies of love and heartbreak, sharing intimate reflections on loss and resilience. As she navigates life's inevitable challenges, the author discovers the path to personal liberation, embracing self-discovery and empowerment. With her signature blend of vulnerability and insight, Gilbert crafts a narrative that resonates with readers seeking solace and inspiration. This memoir is a testament to the human capacity for growth and transformation in the face of adversity, reminding us that love and liberation are always within reach.

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In 'Eat, Pray, Love', Elizabeth Gilbert chronicles her journey as she leaves behind her outwardly successful but inwardly unfulfilling life in the United States. The book is divided into three parts, each set in a different country: Italy, where she seeks pleasure and indulges in the local culture; India, where she delves into spiritual practices and meditation; and Bali, Indonesia, where she aims to find a balance between worldly enjoyment and divine transcendence. The memoir is a personal and introspective account of Gilbert's struggles, growth, and self-discovery during her travels.

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In 'Maybe You Should Talk to Someone,' Lori Gottlieb presents a dual narrative where she recounts her experiences as a psychotherapist working with various patients and as a patient herself, seeking therapy after a sudden and devastating breakup. The book introduces several patients, including a self-absorbed Hollywood producer, a young newlywed diagnosed with terminal cancer, a senior citizen contemplating ending her life, and a young woman struggling with alcoholism and poor relationship choices. Through these stories, Gottlieb sheds light on the therapeutic process, highlighting the complexities of human emotions, the importance of connection, and the universal quest for meaning and inner reconciliation. The book is known for its candid and humorous approach, offering insights into the human condition and the transformative power of therapy.

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We answer questions about a friend who can’t stop one-upping and the tensions around family gift-giving. We share follow-ups about family secrets and post-wedding blues, and bestselling author Elizabeth Gilbert asks, “How do we stop worrying when people we love make bad choices?” And Since-You-Askers weigh in: Do you enjoy getting texts from friends and family throughout the day—or find it annoying?

Have a question or advice to share? Leave a voicemail or write to us at thesinceyouaskedpodcast.com.

Follow along with Gretchen (@gretchenrubin) and Lori (@lorigottlieb_author) on Instagram for the latest on the show.

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Since You Asked is for entertainment purposes only. It’s not a substitute for medical, mental health, or other professional advice. Always consult a qualified professional with questions about your own situation. By sending us your question, you agree we may use it on the show and edit it for length or clarity.

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