Although adolescents are currently the most frequent users of the Internet, many youngsters still have difficulties with a critical, reflective, and responsible use of the Internet. A study was carried out on teaching with a digital role-play game to increase students' reflective Internet skills. In this game, students had to promote a fictional celebrity. The six game levels cumulated in complexity and scope, and students played different roles in each of them (e.g., manager, marketing manager, and journalist). In a one-group pre-test/post-test design, the implementation of the role-play game in four secondary school classes was evaluated using a questionnaire on students' reflective Internet skills. On both pre-test and post-test, girls generally out-performed boys on reflective Internet skills. Repeated measures analyses showed that this gender difference was significantly reduced by teaching with the role-play game. Boys significantly increased their reflective Internet skills, but girls did not. Implications for teaching with this role-play game are presented along with indications how the role-play game could be redesigned to be effective for all students.