This study addresses critical gaps in cross-cultural philanthropy research by examining charitable giving in Taiwan and the United States. It identifies distinct empirical patterns through which individual characteristics are associated with voluntary giving across different institutional contexts. Utilizing propensity score matching, linear regression, and random forest analysis on nationally representative data, the study enhances ecological validity and offers a robust framework for cross-national comparison. Findings indicate that US giving is more individualized and evaluative, whereas Taiwanese giving is more socially embedded. The results provide theoretical and practical implications for culturally adaptive fundraising strategies. Overall, the study demonstrates how institutional contexts condition the relationships between individual characteristics and charitable giving, extending nonprofit research beyond Western contexts.