Paradoxical at first sight, some tourists engage in activities involving negative emotions and even physical pain. Tourism scholars have begun investigating this phenomenon and have called for more of such research. Against this background, the authors introduce to tourism the notion of benign masochism, defining it as a trait describing a person's tendency to embrace and seek pleasure through safely playing with a stimulating level of physical pain and negative emotions. In doing so, the authors root benign masochism in the notion of play from evolutionary psychology and develop a benign masochism scale that is able to predict various tourism outcomes, including willingness to visit a haunted house, to go on a challenging adventure holiday, and to visit a nuclear disaster site. The authors conclude by discussing theoretical and managerial implications as well as limitations and future opportunities for research.