This study compared single (n = 129) and partnered gay men (n = 114) to determine if they differed in their concerns over traditional masculine roles and interest in casual sex, and to measure the relationship between concerns over masculine roles and interest in casual sex. Additionally, a regression model to predict relationship satisfaction was tested. Participants were recruited at two Southern California Gay Pride festivals. Group comparisons showed single men were more restrictive in their affectionate behavior with other men (effect-size r = .14) and were more interested in casual sex than partnered men (effect-size r = .13); and partnered men were more concerned with being successful, powerful, and competitive than single men (effect-size r = .20). Different masculine roles were predictive of interest in casual sex among the two groups of men. Finally, a hierarchical regression analysis found that interest in casual sex and the length of one's current relationship served as unique predictors of relationship satisfaction among the partnered gay men (Cohen's f(2) = .52).