The aim of this study is to respond to Cass Sunstein's question: ‘Why are some nudges ineffective, or at least less effective than choice architects hope and expect?’—particularly in view not only of the rational basis in decision-making but also of the direct influence of emotions on the behavior of those who must choose. In this study, I used findings from psychology surveys, specifically considering the influence of emotions on the fallibility of nudges in social interactions when wealth is compared. Special attention is dedicated to vanity, a combined emotion that leads to emotional choices, which arises in self-presentation and self-comparison when external signs of wealth are displayed. Imagination plays an important role in simulation to the extent that it causes failure in further nudges. In conclusion, I argue that vanity impels people to act differently, as expected of choice architects.