The James Altucher Show

Episode DescriptionJames 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 LearnWhy “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] Rethin