Dark tourism has become an increasingly popular tourist experience in recent years, where people visit former places of punishment – imprisonment, cemeteries, crime, battlefields, etc. Beyond the features of the monument, building or location, the visitor wishes to discover the “dark story” behind it. Within these frameworks, applications can now be developed to meet the needs of visitors, including technologies such as virtual and augmented reality. In this paper, we investigate the possible correlations between gender, personality, and different dark tourism monuments and content. At the same time, we create the “dark content levels” that a dark tourism application could have. Since there are no applications for dark tourism sites, our research starts from the level of content by wondering how dark should dark be.