Brandon, from the episode “How to Not Lose Hope That Your Person Is Still Out There,” is back today to share what’s shifted since we last spoke. We talk about dating in your late 30s after divorce, dating app burnout, asking someone out in real life, and the quiet pressure of timelines around marriage and kids. Brandon opens up about holding hope while preparing for different futures, redefining success, and learning how to build a meaningful life—even when it doesn’t look the way you imagined.

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What It’s Really Like Being a Single Man at 37

Seeing Other People

What It’s Really Like Being a Single Man at 37