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 elicit. In 5 studies, we find that people’s material purchase decisions are more likely to generate regrets of action (buyer’s 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. Demonstrating the robustness of this effect, we found that focusing participants on the material versus experiential properties of the very same purchase was enough to shift its dominant type of regret. 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.