To date, gratitude has been discussed as a positive construct that is linked to various prosocial outcomes, including helping behaviours and altruism, as well as intrapersonal and interpersonal gains such as life satisfaction and social bonds. The emphasis on gratitude as positive has created a dearth of research examining its potential shadow side. This current paper attempts to explore gratitude in a more critical light in order to question whether gratitude always functions in a prosocial manner. First, the theoretical relationship between gratitude, ingratiation and impression management behaviours are explored with reference to social intelligence (SI) and self-monitoring as key constructs that might underlie gratitude's shadow side. This argument outlines that the apparent prosocial nature of gratitude might, sometimes, mask manipulative and self-serving goals. Preliminary empirical evidence of the relationship between gratitude, SI and self-monitoring is then provided. In Study 1, three-hundred-and-eleven participants completed self-report measures on gratitude, self-monitoring and social intelligence. The results demonstrate smallto-medium and significant correlational links between these constructs. Study 2 explored whether practicing gratitude can lead to changes in impression management skills, specifically social intelligence, through the design and delivery of a gratitude versus pride intervention. This small scale intervention (N = 36) provides the first preliminary evidence that practicing gratitude can function to increase participants' levels of social intelligence. The possible prosocial and manipulative functions of this relationship are discussed alongside suggestions for future research avenues.