In this chapter, we outline a theoretical scaffold comprising intercultural awareness and modelling perspective components. Additionally, we report on the outcomes of two exploratory studies that employ Fermi problems to elicit intercultural awareness in pre-service teachers and students. In the first study, the Bikes Problem was successful in promoting 7th graders’ cultural and a-cultural elements in the Fermi problem setting. In the second study, the Teapot Problem enabled pre-service teachers to consider contextual and cultural assumptions in their solutions to the Fermi problem. Consequently, the Fermi problems possess the potential to encourage problem solvers to identify cultural facets of the problem situations, while functioning as a mathematical modelling exercise in enhancing cultural and intercultural awareness.