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Despite the growth of youth mentoring programs in recent years, key questions remain regarding the relative importance of making matches on the basis of shared racial background. Both sides of the argument regarding racial matching are presented, followed by a comparison of the effects of same- vs. cross-race matches involving minority youth (N= 476). Minority adolescents were less likely to report initiating alcohol when placed in cross-race matches. In addition, minority boys in same-race matches reported smaller decrements in scholastic competence and self-worth than did minority boys in cross-race matches. Minority girls in same-race matches reported smaller decrements in school value and self-worth than did minority girls in cross-race matches. Youth, parent, and caseworker impressions of the 2 relationship types largely converged, but the few impressions that differed tended to favor cross-race matches. The methodological limitations and implications of this study are discussed.