The physical and mental health benefits of marriage and partnership are well established, for men in particular. By comparison, very little research has examined within-group differences in social support and well-being within the proportionately large population of single gay men. Employing structured interviews, this study employed Rasch analysis to examine family and friendship ties within a convenience sample of middle-aged and older single gay men (N = 94), and investigated relationships among social support, attitudes, and preferences related to singlehood, and subjective well-being (SWB). As anticipated, measures of social support from family, social support from friends, and adaptation to single status were independently associated with SWB. Unexpectedly, social support did not moderate the relationship between adaptation to single status and SWB, suggesting the possibility of a pathway to SWB for single gay men in the absence of substantial social support.