Metaphors are regularly used by mathematics teachers to relate difficult or complex concepts in classrooms. A complex topic of concern in mathematics education, and most STEM-based education classes, is problem solving. This study identified how students and teachers contextualize mathematical problem solving through their choice of metaphors. Twenty-two high-school student and six teacher interviews demonstrated a rich foundation for these shared experiences by identifying the conceptual metaphors. This mixed-methods approach qualitatively identified conceptual metaphors via interpretive phenomenology and then quantitatively analyzed the frequency and popularity of the metaphors to explore whether a coherent metaphorical system exists with teachers and students. This study identified the existence of a set of metaphors that describe how multiple classrooms of geometry students and teachers make sense of mathematical problem solving. Moreover, this study determined that the most popular metaphors for problem solving were shared by both students and teachers. The existence of a coherent set of metaphors for problem solving creates a discursive space for teachers to converse with students about problem solving concretely. Moreover, the methodology provides a means to address other complex concepts in STEM education fields that revolve around experiential understanding.