In keeping with trends in the most affected regions of the world, Jamaican young women are at greater risk of becoming infected with HIV than their male peers. Cross-generational relationships (CGRs), or sexual relationships between younger females and older men, have been reported as contributing to this increased risk. Utilizing a qualitative research design, this study aimed to (1) delineate the context in which CGRs occurred in some rural communities in Jamaica and (2) investigate the sexual risk behaviors that occurred in these relationships. The results indicated that young women engaged in these relationships for three main reasons: economic gain, status, and emotional support. At the intrapersonal, interpersonal, and community levels based on the social ecological model, findings also highlighted various factors which facilitated the occurrence of these relationships in some rural communities, including the transactional nature of the relationships, as well as family knowledge and encouragement. The results also highlighted the occurrence of sexual risk behaviors, such as multiple concurrent partnerships and lack of consistent condom use, which may increase young girls' risk of exposure to HIV and other sexually transmitted infections (STIs). This study's findings are consistent with previous research and underscore the challenges faced by intervention planners when promoting safe sex.