Fleeting engagements with strangers is a mode of sociality central to urban living such that we cannot understand city life without understanding transient encounters. But in a public lecture, I was asked, “How do you know they’re telling you the truth?” This crystallizes an epistemological conundrum. What can be derived from brief encounters when long-term participant observation is an anthropological gold standard? What is “truth”? Whose truth? And how is it contextualized? This chapter explores the usefulness and limits of a philosophical concept of truth to argue why anthropology should take superficial engagements seriously despite the challenges posed.