This paper reports the findings of research into an educational intervention featuring open-ended mathematical problems situated in "real life" contexts and associated pedagogies. "Money and financial mathematics" is the topic in focus, with tasks termed "financial dilemmas" being trialled by 35 teachers in 16 Victorian primary schools. Drawing on the teachers' reactions to one task, "Catching a taxi," the strengths, challenges, and complexities associated with creating and/or selecting meaningful "real life" contexts for mathematics teaching and learning are discussed.