The goal of this article is to provide conceptual and historical orientation useful for thinking about the emergence of philanthropy in modern South Asia. Conceptually, the article suggests the need to approach the expression of philanthropy in early colonial Bengal in terms of processes of imitation. To do so, we must overcome the stigma attached to the idea of imitation within both nationalist and post-colonial thought. In the particular context of early colonial Calcutta, local actors entered into intimate relationships with Europeans and these relationships provided occasions to borrow, translate, and retool a range of ideas and practices relevant to new modes of public charity. The importance of attending to historical context is suggested by reading such early colonial developments against the grain of late nineteenth-century perspectivesa time when Bengalis grew anxious about cultural imitation. Rather than deferring to these late-colonial anxieties over imitation, we need to situate them within a critically informed historical framework. To do this, the present article draws on the writings of the Brhmo intellectual Rajnarain Bose, who pondered the relationship between an earlier colonial moment (then') and his own late-colonial now'. Close reading of Bose allows us to plumb the nature of late-colonial anxiety about cultural borrowing while opening up a new perspective on imitation and intimacy in early colonial Bengal that is not predicated on the teleology of the late-colonial modern.