Why is teaching in context an important option to consider in the teaching of mathematics? What does it mean to teach mathematics from and in contexts? And what are the possible challenges associated with this practice? The aim of this paper is not to provide a comprehensive answer or solution to these questions. We attempt rather to address these questions specifically with regard to South Africa and the theory of Realistic Mathematics Education. In this article we consider a vignette of a more formal and traditional mathematics lesson and then suggest possible reasons why we need to be teaching more in context. Furthermore we discuss the application of the theory of Realistic Mathematics Education as a potential approach to facilitate teaching in context. Finally we present some challenges associated with this practice.