The experience of emotions in decision-making processes involves a recursive cycle: emotions not only influence the decisions people make, but the decision-making process also changes people’s emotional state. In this dissertation, I focus on the interplay of choice and sadness, given that sadness is a very pervasive emotion. First, I examine whether and why shopping can reduce residual sadness (i.e., whether retail therapy works). Sadness is strongly associated with a sense that situational forces control the outcomes in one’s life, and thus I theorize that the choices inherent in shopping may restore a sense of personal control over one’s environment, thereby reducing residual sadness. I find that making either real or hypothetical shopping choices helped to alleviate sadness. In addition, I find support for my hypothesis that the underlying mechanism of this effect is personal control restoration. Yet, for consumers to take advantage of the benefits of retail therapy, they must be willing and able to make purchase decisions. However, the experience of sadness tends to increase a person’s sense of uncertainty, which can in turn influence a consumer’s ability to make decisions. I find that sadness reduced decisiveness, even when being indecisive is financially costly. Supporting the uncertainty process explanation, I also find that anger (a negative emotion that is not associated with a sense of uncertainty) did not reduce decisiveness. The interplay of choice and sadness, then, is something of a viciously paradoxical problem - one’s ability to alleviate his or her sadness by making decisions is actually impaired by being sad in the first place.