This report from C-Change/FHI 360 documents a study that explored the dynamics of cross-generational relationships in Jamaica, with the aim of informing communication programs working to decrease cross-generational sexual practices and their related risks, including gender-based violence (GBV) and HIV. This study defined cross-generational sex as sexual behavior between two people who are at least 10 years different in age. The authors found that key motivators for participating in these relationships were sexual gratification and emotional and financial support. The primary motivator of cross-generational relationships for males (older and younger) was sexual gratification and for females was emotional support. Financial and material gains were also key benefits for younger males and females and a component of most cross-generational relationships. Participants' motivations and practices mirrored the perceived norms they reported.