Previous research has established that experiential purchases tend to yield greater enduring satisfaction than material purchases. The present work suggests that this difference in satisfaction is paralleled by a tendency for material and experiential purchases to differ in the types of regrets they generate, as well as in the conditions required to prompt regret. In chapter one, I present five studies demonstrating that people's material purchase decisions are more likely to generate regrets of action (buyers remorse) and their experiential purchase decisions are more likely to lead to regrets of inaction (missed opportunities). These results were not attributable to differences in the desirability of or satisfaction provided by the two purchase types. This pattern of regret is driven by the tendency for experiences to be seen as more singular-less interchangeable-than material purchases; interchangeable goods tend to yield regrets of action, whereas singular goods tend to yield regrets of inaction. While chapter one identifies differences in what types of regret are most likely for material and experiential purchases, chapter two considers how likely a regret is to form in the first place, and what might prompt it. I present six studies that examine the relationship between dissatisfaction and regret, and find that the slope of that relationship is different for material and experiential goods. It takes just a little dissatisfaction to prompt regrets of action for material goods, but people must be significantly more dissatisfied with an experience before they regret their purchase. Interchangeability mediates this effect, and I also explore potential mechanisms for this effect, finding that purchase type-by way of interchangeability-influences both the likelihood that someone will engage in counterfactual thought, and the degree to which those counterfactual thoughts are emotionally impactful.