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For West Indian colonials whose cultural traditions are colored by the idealizations of a colonizing British mother country, discovering one’s place in familial and national structures involves making real and imagined journeys to that mother country. In Andrea Levy’s Small Island, two Jamaicans, Hortense and Gilbert, grow up in early twentieth-century, colonial Jamaica and later immigrate to WWII-era England. Through their narratives of both places, Levy demonstrates how the dynamic of the colonial relationship—the values and hierarchies inherent in the relationship between the mother country and her colony—impact mother-child relationships, self-understanding, and identity. In this article, I assert that the existential uncertainty that the colonial relationship creates—the desire and unpredictability of human relationship and the ensuing ambivalence about psychological survival—consistently holds in tension two important concepts: help and humiliation. The structure, pressures, and oppressions of the colonial system in Jamaica and England lead Hortense and Gilbert to either experience or inflict scenes of humiliation that arise from making relational sacrifices.