This is an exploratory qualitative study of 10 seniors (5 men and 5 women), who remarried or lived together after the age of 65. They were all Jewish, lived in Toronto, Canada, and had been married previously. The subjects were interviewed in their own homes, using a questionnaire. The study attempts to explore the pathways to recoupling, how the partners met, the differences between the first and second partners, and the major issues faced by the subjects in moving into a new relationship. The results in this article are significantly presented through the words of the respondents. This gives the reader the flavor of what is involved in senior relationships. The conclusions summarize the major findings of the study, and make suggestions for further research. We focus on implications for health and wellbeing from our findings.