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Teacher, academic, and humorist Leo Rosten wrote, “Humor is the affectionate communication of insight” (as cited in Eckhardt, 1992). While perspectives differ on humor’s use for affiliative purposes, an analysis of humor in intercultural conversations demonstrates the intricacies of how this sharing of insight may succeed or fail. This chapter begins by defining culture as the foundation on which individuals orient to one another. This foundation functions as a shared framework of meanings by which interactants manipulate symbols to convey thoughts, feelings, and insights, including humor. In intercultural interactions the absence of such a shared framework poses challenges to communicators and it is this awareness that potentially influences perceptions of and responses to humor usage. The examination of humor in intercultural interactions has predominantly been studied from a conversation analytic perspective. This approach has generated ample descriptions of functions and forms of humor and for this chapter we have drawn on this body of work for our starting point. However, by definition, conversation analysis favors description over explanation and prediction. It is proffered that a deductive approach to humor in intercultural interactions allows for the application of general principles that may guide us in the understanding of why humor attempts in the intercultural context succeed or fail. The application of communication accommodation theory and expectancy violations theory leads to the conclusion that the nonnative speaker (NNS) should generally refrain from humor attempts. It is also argued that the cultural understanding and linguistic skill level of NNSs can unintentionally provide instances of humor that may function affiliatively while simultaneously marginalizing them. We begin with a decomposition of culture as shared understanding.