This article examines the diverse ways in which people experience being strangers in public space. Based primarily on the journal entries of teenagers in New York City on their trips, we show the different ways in which riders experience being a rider amid diversity and norm violations. Some teenagers see being a rider as an engaging role, some as a detached role, and others as a precarious role. All the teenagers use folk theories to navigate the social world, but how they use them varies depending on how they experience being a rider. Finally, riding in groups shifts their experiences and interpretations in complex ways that make riding more enjoyable, but filled with additional emotional tensions. Building from previous theories and studies on strangers and public spaces, this article contributes to longstanding debates in sociology over how people interact with others in urban environments.