The School of Greatness · May 22, 2026 · 01:15:50

Why You Keep Choosing the Wrong Person (And How to Finally Stop) | Faith Jenkins

Attorney, television judge, and author Faith Jenkins joins Lewis to share her practical framework for choosing love wisely and avoiding the trap of settling in relationships. Drawing from her experience presiding over divorce cases, her own journey through over ten relationships before marrying at 42, and personal encounters with heartbreak and rejection, she explains how to identify red flags early, practice radical acceptance, and build emotional maturity through each chapter of your dating life.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Highlights

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The 'Don't Settle' Principle

Faith Jenkins argues that many people settle in relationships out of fear of being alone, and that knowing your worth is essential to finding the right partner.

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Identifying Red Flags Early

Jenkins explains that recognizing early signs of incompatibility can prevent years of relationship misery.

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Radical Acceptance in Dating

Jenkins discusses radical acceptance as a tool for moving through heartbreak and rejection without losing self-esteem.

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Building Emotional Maturity Through Dating

Each dating experience, whether successful or not, is an opportunity to grow emotionally and refine what you're looking for in a partner.

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References

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Sis, Don't Settle: How to Stay Smart in Matters of the Heart — Faith Jenkins — Guest's book — the foundation of the episode's advice on dating and relationships

Misc

✧Faith Jenkins had over 10 relationships before marrying at 42.

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