There is considerable disagreement and even confusion over what forms of border-crossing philosophizing are most appropriate to our times. Are comparative, cross-cultural, intercultural, blended, and fusion philosophy all the same thing? Some critics find what they call “comparative philosophy” to be moribund or problematically colonialist; others assert that projects like “fusion philosophy” are intellectually irresponsible and colonialist in their own way. Can we nonetheless identify a distinctive project of comparative philosophy and say why it is important? Based on a broad survey of approaches, this essay offers schematic answers to these questions, clarifies some persistent confusions, and stresses the constitutive gamble that lies at the heart of all comparative philosophy. There are several different ways to do comparative philosophy well; which method to employ depends on the values that motivate and the pragmatic situation that frames one’s inquiry, and on the ways in which one or more communities receive and respond to one’s contribution.