Research into the causes of hurt feelings has generally examined the impact of single predictors. The current article builds on previous literature by examining the interactive effects of several key elements of hurtful events in predicting the intensity of hurt. Two studies using community samples of women examined interactions between the type of hurtful event, the importance of the perpetrator, and victim hurt-proneness in predicting variance in hurt intensity. Study 1 (n = 475) used a series of scenarios as the hurtful stimulus while Study 2 (n = 380) used a number of recalled hurtful events. Both studies replicated previous bivariate relationships between perpetrator importance and hurt-proneness and the intensity of hurt, while the first study also demonstrated a significant effect for type of hurtful event. Both studies also found a significant three-way interaction between these variables, indicating that victim hurt-proneness only predicted the intensity of hurt at lower levels of event severity and perpetrator importance. It is concluded that the experience of hurt is multidimensional and contextual. Future directions for research involving gender differences and interventions for individuals and couples are discussed.