Past research has indicated gender differences among narcotic users that have implications for the prevention and treatment of substance abuse; however, little is known about these differences among crack cocaine users. The purpose of this secondary analysis was to compare the relational context of male and female crack cocaine use. Data from open-ended, structured interviews with 46 predominantly African-American women (n = 23) and men (n = 23) were compared using manifest content analysis. Women were more likely to begin, use and/or maintain their use of crack in the context of more intimate opposite sex relationships, while men were more likely to begin their use with male friends and associates and to maintain drug use with income from jobs and selling drugs. Overall, relationships (both sexual and familial) were a more prominent aspect of crack use for women while enterpreneurship was more salient for men. These findings suggest the need for gender-sensitive prevention and treatment strategies.