Negative experiences were more likely to occur when adolescents interacted with people they did not know and when an intrinsic motivation for engaging in sexual interaction was missing. There was a strong relation between bothersome experiences and being cyberbullied. Adolescents with a higher level of online disinhibition and with low self-control were more likely to engage in both sexual communications as well as in sexting. Identifying which incident characteristics and characteristics of adolescents are related to problematic online sexual interactions is a prerequisite to design more personalized tools for vulnerable adolescents.