Male couples place the issue of extra??relational sex (ERS) in their committed relationships at various points on a continuum between monogamy and non??monogamy. Further, many couples move about on this continuum over the course of the relationship, according to their changing wishes and desires. Making the right choice or transitioning from one relationship style to another is not always straightforward and unproblematic. Some male couples may benefit from therapeutic support at these crucial times. This research seeks to contribute to knowledge that could inform sensitive and respectful practice on the part of therapists and others who work with the relational concerns of gay men. Using qualitative methodology the research questions explored how gay men negotiate the place of ERS with their partners, the strategies they use to manage ERS, and their beliefs about the effects of their choices on themselves and their relationship. A purposive sample of 24 Sydney gay men (six single and 18 partnered) aged between 22 and 68 participated in the research. Data were collected through semi??structured interviews and subjected to thematic analysis. Despite diverse experiences of ERS, a core set of processes appeared central to relationship satisfaction and function. The knowledge produced by this research provides a number of ways for therapists to orient themselves to the therapeutic terrain of work with gay men and ERS while remaining alive to the unique and particular characteristics of the male couple relationship before them.