Online grooming of young people for sexual exploitation and for radicalisation is a global issue. The importance of quality education that equips young people to develop their digital resilience and critical thinking skills is essential as a way to prepare them to use online technology safely and appropriately. In this article, we look at two innovative and creative social media simulations that were developed by the Centre of Child Protection for the training of professionals in child protection issues. Using social constructivist perspectives on learning the simulations focus on the role of social media to facilitate understanding and critical analysis of online environments. The simulations respond to the contemporary landscape of social media and the complexities of grooming, child sexual exploitation, extremism and radicalisation, issues that are often addressed in schools through pastoral care. We look at the relationship between creative engagement via the online social media simulations and their use in teaching these complex topics, and take an empirical view to evaluate this creative approach as a scaffold tool for teachers to help children and young people to think critically and respond positively to the navigation of complex lifeworlds. We surveyed trained professionals who had all undertaken CPD training with the Centre of Child Protection in either of the two simulations from March 2015-April 2017. Out of 308 responses, 146 identified themselves as educators, and it is their feedback that we discuss in this article.