Case Kenny: Stop “Settling Down” and Start “Settling Up”

Episode Description

James sits down with Case Kenny, author of The Opposite of Settling and host of New Mindset, Who Dis?, to talk about how our expectations around relationships shape the way we date and commit. Case shares the research, stories, and mindset shifts that helped him go from avoiding commitment in his twenties to finding fulfillment in a relationship that amplifies his independence. This episode challenges old narratives about “settling down” and offers a practical framework for building relationships that energize rather than diminish.

What You’ll Learn

• Why “settling down” is the wrong framework for love—and how to reframe it as “settling up.”
• How the liking gap skews our perception of how others see us, and what that means for dating.
• The importance of dating to be seen instead of dating to be liked.
• Why non-conforming traits (your “weirdness”) can actually make you more attractive.
• How playfulness and humor serve as the foundation for strong, lasting relationships.

Timestamped Chapters

• [00:00] Rethinking independence in relationships
• [01:00] James introduces Case Kenny and The Opposite of Settling
• [02:00] Why the phrase “settle down” shaped Case’s early resistance to commitment
• [05:00] Letting relationships fade: what Case learned from avoidance
• [07:00] Meeting Emily and the power of a “slow burn”
• [09:00] Timing vs. compatibility in finding a partner
• [11:00] The “liking gap” and how it affects dating behavior
• [13:00] Performance mode vs. being present
• [14:00] Dating to be seen, not just to be liked
• [15:00] The value of non-conforming traits in attraction
• [17:00] From introversion to self-expression through podcasting
• [20:00] Knowing yourself before you can know what you want
• [21:00] The peak-end rule and distorted memories of relationships
• [23:00] Appreciating past relationships without villainizing them
• [25:00] How the brain can reinforce unhelpful dating patterns
• [27:00] The case for showing up fully on first dates
• [29:00] Learning from rejection and getting clarity fast
• [31:00] Why regret often comes from the wrong relationship, not from being single
• [33:00] Playfulness as the true purpose of relationships
• [35:00] Humor and “bids for connection” as relationship foundations
• [37:00] The importance of noticing your partner
• [38:00] Why James listened to standup comedy before dates
• [39:00] Wrapping up with Case Kenny

Additional Resources

• Case Kenny — The Opposite of Settling: PenguinRandomhouse.com
• Case Kenny — Single Is Your Superpower: New Mindset, Who Dis?
• New Mindset, Who Dis? (Apple Podcasts): Apple Podcasts
• The Gottman Institute — “Bids for Connection” (overview): Start paying more attention to bids. Gottman Institute
• Research — “The Liking Gap” (Boothby et al., 2018, PDF): Yale Clark Relationship Lab. Clark Relationship Lab
• Explainer — Peak–End Rule: The Decision Lab
• Case Kenny on X (Twitter): @thecasekenny

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