This investigation examined the links between self-monitoring propensities and orientations toward sexual relations. A factor analysis of behavioral and attitudinal survey data revealed that high self-monitoring individuals tend to establish an unrestricted orientation toward sexual relations (such that they may engage in sex with others to whom they are not necessarily psychologically close), whereas low self-monitoring individuals tend to establish a restricted orientation (such that they will engage in sex only with partners to whom they are psychologically close). At the behavioral level, high relative to low self-monitoring individuals indicated that they had a larger number of different sexual partners within the preceding year, could foresee themselves having sex with a larger number of different partners within the next 5 years, and were more likely to have engaged in sex with someone on only one occasion. At an attitudinal level, low relative to high self-monitoring individuals indicated that they would be more reluctant to have sex with someone to whom they were not committed, and that they would be more uncomfortable with, and less likely to enjoy engaging in, casual sex with different partners. Possible origins and implications of these contrasting orientations are discussed.