Dating apps have revolutionized how we meet, but in doing so, they often short-circuit the vulnerability required for real connection. After going on 25+ dates in one month, I discovered that while apps are great at generating matches, they rarely help us transition to meaningful, in-person relationships—and may even trap us in fantasy connections that never materialize. These platforms thrive on keeping us swiping, not settling down, optimizing for engagement over emotional growth. Yet, meeting face-to-face (doing the hard thing) was where I found the most value, growth... and even a few sparks. What we need now is a shift in how dating technology is designed: tools that don’t just stoke desire but support courage, presence, and the messy, beautiful work of building something real.

In this episode, I sit down with my good friend Elinor to talk about navigating conversations about Israel and Palestine in the wake of October 7th 2023. We recount some difficult discussions, why it’s been so easy to feel misunderstood — or to misunderstand others, and how our backgrounds shape the way we see things. We also get into how tech — especially social media and resulting disembodied conversations — amplifies extremes, pigeonholes, and makes it harder to have thoughtful, nuanced dialogue. This is not about taking sides. It’s about how to stay human in the middle of something painful and complex.

In this first episode, I explore a deeply personal topic—the sudden death of my brother Christopher in 2023 at just 27 years old. Joined by my surviving brother James, we reflect on Chris’s life, our grief, and the strange dissonance of losing someone so young. We end by exploring whether AI could—or should—play a role in preserving and even recreating a loved one’s consciousness.