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The James Altucher Show

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

The James Altucher Show

James Altucher

Society & Culture, Talk Radio, Writer, Philosophy, Comedy, Chess, How To, Entrepreneurship, Jay, James, The James Altucher Show, Altucher, Author, Jay Yow, Education, Jay The Engineer, Business, James Altucher

4.6 • 2.7K Ratings

🗓️ 19 August 2025

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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


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Transcript

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0:00.0

Today on the James Altiger show.

0:03.4

I think the right relationships should make you more independent, a total reversal of how I used to think of a relationship.

0:11.1

And I reference a little bit of research in that as well.

0:14.7

I kind of refuse myself to be like, wow, this is like, I want to lock this woman down and, you know, get government involved in it and marry her deep down. I was like, I don't know if I'm a relationship guy. We are adopting expectations, that is assumptions about how fast the relationship should go, and it's really not true to us, and there's no right way, and there's no right pace of a relationship. And, you know, a lot of people nowadays talk a lot about, for women, it's the right person and for men it's the right time.

0:40.7

My whole mindset is that when you're dating, don't date to be liked, date to be seen.

0:50.8

This isn't your average business podcast, and he's not your average host.

0:55.8

This is the James Altager show.

1:07.6

I've got Case Kenny with me, the author of the new book, The Opposite of Settling, and also the host of the podcast, New Mindset, Who Dis?

1:19.4

Case, welcome to the show.

1:20.9

Thank you.

1:21.4

Thank you for having me, James.

1:22.4

Appreciate it.

1:23.5

Now, Case, I've been in the dating world.

1:26.0

I've been in the married world, probably more times than I would like to admit for both.

1:30.8

And the opposite of settling.

1:33.7

Maybe I want to hear you describe what you mean by settling, but also I want to hear your story.

1:40.4

I want to hear like when you felt you might have settled and then started to work on the

1:45.1

ideas that became so poignant in your book. For sure. Well, yeah. I mean, I think, you know,

1:50.5

I wrote the book because a couple years ago, I sat down and I was thinking about like some of my

1:56.3

younger self-resistance to commitment and relationships, right? So like like, classic 20, mid-20-something guy, avoidant mentality. And I was thinking back about like why maybe I was that way and younger men are that way as well. But, but I'm sorry to interrupt, but can I ask, what way were you? What does it mean? Like, give me, like, what was a specific example? I just mean not, not bought into the concept of a relationship right so like not

2:19.8

so like you would be dating someone and what would happen and then you know classic male avoidant of

2:25.2

letting it die because you didn't see the purpose of a long-term commitment and marriage and you know

...

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