Owen Barfield, a literature graduate and one of the celebrated Oxford “Inklings”, worked as a poet and author for a decade before working for a quarter of a century as a solicitor in the family firm in London. His book This Ever Diverse Pair provides a personal insight into what it means to live a life polarized between practice in literature and law, and his book Poetic Diction: A Study in Meaning presents the idea that such polarities can generate poetic energy and pleasure. This chapter proposes as a definitional distinction between law (in its most regular and regulatory mode) and poetry (in its most playful, least prosaic mode) that law seeks to close down the complexity of a word’s linguistic significations whereas poetry seeks to open it up. It asks whether law and poetry, when placed in polar opposition to each other, might become what Barfield calls “sweet enemies” and produce pleasure through their play.