Trust has proven to be a vital social capital. It has been implicated in a myriad of socially beneficial initiatives. While trust vested in familiar others remain important, trust extended to strangers is crucial to the continued development of social capital. This is because such interaction, though risky at times, forms a springboard to untapped opportunities. Using a multi-round trust game and self-report assessments the present study explored explanations for observed cultural differences in trust in strangers. Data was drawn from university students in Ghana and Hong Kong. Factor analysis showed that self-report trust in strangers was associated with trust in people of another religion and people of another nationality among Hong Kong Chinese, but was associated with trust in family members and people whom one knows personally among Ghanaians. While Hong Kong Chinese students reported higher level of trust in strangers, Ghanaian students showed higher level of trust in standard behavioural measure. Perceived nepotism in public institutions explained the observed cultural difference in self-report trust in strangers. Self-report trust in strangers and perceived nepotism in public institutions did not relate to behavioural trust in both samples. However, culture specific results with the behavioural measure indicated that dealing with a generous or thrifty individual impacted trust significantly. In both samples, participants dealing with a generous individual showed higher behavioural trust compared to those dealing with a thrifty individual. These results suggest that the influence of context on trust is twofold: distal, contextual factors, such as perceived nepotism in public institutions are influential to the cultural differences in self-report trust, whereas proximal, situational factors, such as generosity of a stranger, have more impact on actual trust behaviours. Altogether, this research showed that the contexts under which people function have substantial impact on trust. Specifically, individual’s experiences with the government institutions in a sociocultural context affect their tendency to trust unfamiliar others, but one’s immediate interaction with another person is more influential to their enactment of trust in a particular situation. Future research on trust should pay more attention to the effects of contexts, depending on how trust is operationalized.