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In some cultures, individuals are free to pursue careers that match their personalities. In others, familial and societal expectations regarding career paths may restrict the links between individual personality and interests. Gender role expectations also may vary across cultures and may be associated with gender differences in interests. Past meta-analytic research has shown some career interests are related to personality traits (Barrick, Mount, & Gupta, 2003; Larson, Rottinghaus, & Borgen, 2002), but the cross-cultural variation of these relationships has not been sufficiently explored. Interest and personality data were obtained from an archival data set of 391,485 individuals from 20 countries. Results indicated that in cultures with high in-group collectivism, connections between personality traits and occupational interests may be less pronounced. Cultural gender egalitarianism moderated the level of gender differences in interests, unexpectedly demonstrating that gender differences may be wider in egalitarian cultures. Implications for career guidance in multicultural settings are discussed.