In this exploration of human connection, Daniel May and Cade Embery explore the complexity of caring, challenging the conventional wisdom that support is merely about providing solutions. They argue that true caring is a deliberate, often effortful practice of active listening and “reconnaissance” - the patient gathering of context before intervention. By navigating the fine line between helpfulness and enabling (the “emotional cigarette”), and embracing the transformative power of vulnerability, this conversation offers a reflection in building trust.