The present study sought to establish a relationship between others’ expressions of self-conscious emotions and the observer’s theory of mind. By manipulating the type of expressed self-conscious emotions and the meaning of the event, this study demonstrated that the expression of guilt (vs. shame) followed by the same immoral behavior leads to a greater level of hypocrisy perception by uninvolved observers, indicating that people expect a person to show greater future behavior change from their expressions of guilt than of shame. It should be noted that in Study 2, consistent with the findings of Study 1 and that of Stearns and Parrott [30], the difference in the direct change-expectation ratings between shame and guilt conditions was not significant. It appears, then, that additional contextual information, for example, personal-consistency information, as in the present study, is critical in distinguishing subtle differences in the social meaning of guilt and that of shame.The present study contributes to the extant literature on emotions by exploring the observer’s perspective of the expression of guilt and shame by other people, which is a relatively under-studied subtopic in this field. Although some researchers have speculated (e.g., [39]) and indeed tested (e.g., [30,31]) the idea that guilt signals greater potential for future change to social observers when opposed to shame, no empirical evidence had been reported so far. Thus, the present study is the first to demonstrate the systematic difference in people’s naïve theories of shame and guilt and the contingency of future change upon the former. Indeed, differentiating often similarly experienced emotions would be even more challenging from the observer’s perspective (e.g., [7]) because shame and guilt are similar in the eyes of observers who tend to construe others at a more abstract level than themselves [40]. The present study suggests that placing guilt and shame in a future context could be an effective way of navigating the distinctive nuances in the social meanings of guilt and shame. By manipulating shame and guilt in a future-specific context, this study distinguished the implications of guilt and shame for future changes in the eyes of observers. Furthermore, the present study highlights the moral standing of self-conscious emotions from the perspective of social observers. In the literature on emotion, guilt is considered a typical moral emotion because it promotes moral motivation [41,42,43] while shame is considered to have a less-clear identity as a moral emotion. In line with the social-functional perspective [12], this study suggests that the expression of guilt (vs. shame) is more valued by others, especially when the same event is expected to reoccur, because guilt signals a promise for future change, a reassurance missing from the symbolic perception of shame. Consequently, some individuals may be tempted to exaggerate their guilty feelings, the “correct” emotion [22], in the hope they could then receive greater forgiveness from the affected victim or uninvolved social others. However, this study suggests that expressing guilt may risk one being perceived as a hypocrite when one commits the same act again. In such cases, exhibiting remorse would lead to more negative evaluations of the person because people would see the person as insincere (e.g., [44,45]). Considering that hypocrisy judgment is closely related to feelings of trust, the present findings will help us understand how expressions of shame and guilt, along with other situational factors, differentially influence the perceived authenticity of remorse, especially in legal settings (e.g., [46]).