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

17 snips

Aug 19, 2025

In a dynamic chat, Case Kenny, author of 'The Opposite of Settling' and host of 'New Mindset, Who Dis?', shares insights on modern relationships. He challenges the notion of 'settling down', advocating for 'settling up' to enhance personal growth and independence. Case discusses how the 'liking gap' influences dating perceptions and the significant shift from dating for approval to seeking genuine connections. He also emphasizes the charm of being quirky and the role of humor in crafting lasting partnerships.

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INSIGHT

Reframe Settling As Growth

The phrase “settle down” framed relationships as loss and scared Case away from commitment in his twenties.
Reframing to “settle up” made relationships feel energizing and independence-amplifying.

ANECDOTE

Letting A Relationship Fade

Case let a promising relationship fade because he refused to pursue the next steps like meeting families or planning a future.
He now cringes at his younger passive behavior and regrets not communicating more directly.

INSIGHT

The Liking Gap Misleads You

The 'liking gap' shows we systematically underestimate how much others like us after conversations.
That underestimation pushes people into scarcity and self-censoring performance mode.

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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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