Over the past seventy-five years, the standard assumption in cultural and anthropological studies has been that the Anglo-American approach to cross-cultural mission work in the 18th and 19th centuries was motivated by a mix of cultural imperialism, spiritual superiority, and ethnic or racial hubris. On this reading, talk of being compelled by an ardent love for Christ to run any risk in order to rescue perishing souls only papered over the ugly appetite of empire. This paper attempts to interrogate the motivations underneath the remarkably common cross-cultural approach across the long 19th century (1789–1914). But it seeks to do so in a more charitable manner, as an exercise of applied history. Specifically, it will consider the opportunities Anglo-American missionaries would have to experience “otherness” before leaving, the exemplars (especially those written presentations of their adventure) whom they sought to emulate, and the education they received before their departure. Tracing the institutional response to the dawning awareness that missionaries come from a culture to a second culture with the gospel will provide fruitful points of reflection for our efforts to take the gospel of Nicaea to our nation, and to the nations, for another 1700 years.