This chapter presents a study of the courtship patterns from five mature, Afro-Caribbean, Jamaican couples who have been together for twenty to fifty years. Of interest are the descriptions of what they consider to be love, what keeps them together and how they see the future for themselves and the next generation of Jamaicans as lifelong partners. The data are collected through phenomenological in-depth interviews. Video recordings of the interviews were analysed for the psychosocial and psycholinguistic cues. The psychosocial themes include: their courtship patterns, the types of love displayed, and the experiential intimacy demonstrated by the couples. Psycholinguistic themes include communicative dominance with regard to who told the story, how much they referred to the other partner, whether the stories were similar or vastly different and conversational turn-taking. The results show that couples in this age group demonstrate less typically romantic courtship rituals than would commonly be expected of North Americans and Europeans. The types of love demonstrated are generally less likely to be consummate, but rather storge and pragma.