In recent years a great deal of work on mathematical word problems has focused on efforts to bring more of "real life" into the problems themselves and students' uptake of these problems. Following on from earlier studies of the word problem as a pedagogical and literary genre, the author argues that we cannot unproblematically assume an ability to know and to represent or match "real life" in word problems. The author uses the work of contemporary theorists Bakhtin, Lacan, Zizek and Baudrillard, including concepts like the chronotope, the Lacanian Real, Imaginary and Symbolic, simulacra, and impossible exchange, to argue that conditions of our postmodern world render transparent matchings of word problems with "real life" unsustainable.