This paper—an auto-ethnographic exploration, of sorts, of the relationship between urbanism, loneliness, and commerce—is one organized as a nonlinear narrative, arranged in a series of first- and third-person vignettes. It revolves both around lived experience, and—more obliquely—around existing sociological literature about urban development’s effects on the human condition, borrowing equally from scholarship published between 1903 and 1989 and from personal anecdotes set in the recent past and immediate present. Existing literature establishes the increasing inaccessibility—and gradual death—of “third spaces,” coupled with urban design’s ceaseless trend towards increased commercialization and emphasis on consumerism, as one of urban loneliness’ primary reagents, creating and perpetuating citydwellers’ sociological maladjustment and maladaptation; personal experience puts these insights into practice, demonstrating their veracity and establishing an imperative for change. Ultimately, this paper seeks to frame the very nature of the modern American city as the foremost contributor to its own death—a slow, protracted form of urban suicide—and tacitly endorses a set of mechanisms and interventions, both municipal and individual, by which it might be countered.