This study examined the influence of the relationship context where adolescent sexual activity takes place on contraceptive decisions. The data were collected in a specially designed survey carried out in May 2000 on 1,438 adolescent males aged 13–19 residing in favelas (urban slum areas) of Recife, Brazil. A logistic regression analysis of condom use at last sexual intercourse and a multinomial logit analysis of contraceptive method choice were performed for 678 sexually active adolescents. Educational attainment, degree of knowledge of HIV transmission and prevention, and condom use at first sexual intercourse were found to be significantly associated with current condom use. Regarding the relationship context, the analysis revealed that adolescent males in steady relationships were less likely to use condoms, less likely to regard themselves at risk of HIV infection, and more concerned about pregnancy prevention than adolescents in casual relationships. Differentials in condom use by type of relationship, however, did not result from a higher rejection of contraception by steady partners but from their higher likelihood to rely on other contraceptive methods. Results suggest that prevention campaigns need to take into account the intimate context where adolescents assess potential health risks, and to address the divergent symbolic meanings condoms may have in different types of relationships. If an increase of condom use among stable sexual partners is pursued, public health campaigns might need to romanticize condom use as a sign of love and trust and place more emphasis on the benefits of dual protection.