Is it possible to speak English with Spanish meanings, or vice versa? Are the two languages incompatible? How does a bilingual person maintain stable use of a word when it has different meanings in each language? Are dual linguistic registers separate or complementary? What establishes a division between the two languages? Is this linguistic border ever crossed? This note examines these questions in the context of Ernest Hemingway’s use of the words “Papa,” “papa,” and “papá” in Cuba and Key West after 1930. Through a multi-competence perspective of bilingualism, it argues that Hemingway’s use of “Papa/á” after 1930 corresponded to its meanings in Caribbean Spanish as well as English, a reading that nuances and complicates the powerful paternalist notions generally associated with Hemingway’s famous nickname.