In this article, I apply the stress process model as a framework to understand sexual sociality and its impact on health among urban gay men in a large North American gay enclave. Data consisting of in-depth interviews with 70 gay men coupled with three years of fieldwork demonstrate a sexual status order that privileges caucasian, middle-class men in their twenties and early thirties, and that disadvantages black and Asian men, men over 40 years of age, and poor men. Men with low sexual status faced significant stressors in the form of avoidance from others, stigmatization, and rejection. These stressors, in turn, taxed personal resources, including self-esteem, sense of social support, and sense of control, and they also negatively affected emotional states in the form of depression and anxiety. Finally, some low status men were unable to consistently negotiate condom use as a consequence of a history of field stressors and diminished personal resources. The results suggest that more work on sexual status structures and their connection to health is needed, both within gay enclaves and across a broader spectrum of sexual subcultures.