The current study examined the role of two constructs in potentially explaining the linkages between Snyder's (1974) self-monitoring construct (adapting behavior to fit social expectations like a social chameleon) and authenticity (behaving consistently with one's thoughts)/well-being. The proposed explanatory constructs were theory of mind (ToM; predicting feelings/thoughts of others) and Machiavellianism (manipulating others for one's own benefit), with the first representing a skill set facilitating the healthy negotiation of successful relationships and the second representing a motivational mindset focused on obtaining advantages and status. Participants (N = 384, 17 to 60 years; M-age = 19.49; 69.5% female) responded to a questionnaire that included tests and measures of the aforementioned constructs. Regression analyses indicated that the link between other-directedness, one of two major self-monitoring dimensions, and authenticity (as well as well-being) could be explained in part as a function of Machiavellianism. On the other hand, the eyes-test, which serves as a measure of social-perceptual features of ToM, was not found to be related to self-monitoring, authenticity, or well-being in our data. The implications for advancing our understanding of the linkages between self-monitoring and authenticity are discussed.