Two mathematics teacher educators (MTEs) discuss the mathematical contexts generated by prospective teachers (PTs) when pushed to look for relevant mathematics in their lives and communities. Through collaborative teacher action research focused on iterations of collecting, categorizing, and discussing PTs’ mathematical contexts, and posing selected examples for PTs’ own examination, layers of learning occurred for both PTs and MTEs. PTs began to craft more personalized, story-like contexts, seemingly noticing more mathematics in their lives. MTEs were unexpectedly pushed to clarify their thinking about what it means to develop contexts that are authentic and relevant, and to contemplate how their actions were influencing the mathematical stories told by PTs.