People tend to flirt only with serious things--madness, disaster, other people's affections. So is flirtation dangerous, exploiting the ambiguity of promises to sabotage our cherished notions of commitment? Or is it, as Adam Phillips suggests, a productive pleasure, keeping things in play, letting us get to know them in different ways, allowing us the fascination of what is unconvincing? This is a book about the possibilities of flirtation, its risks and instructive amusements--about the spaces flirtation opens in the stories we tell ourselves, particularly within the framework of psychoanalysis. Phillips looks at life as a tale to be told but rejects the idea of a master plot. Instead, he says, we should be open to the contingent, and flirtation shows us the way. His book observes children flirting with their parents, our various selves flirting with one another, and literature flirting with psychoanalysis. As Phillips explores the links between literature and psychoanalysis--ranging from Philip Roth to Isaac Rosenberg, Karl Kraus to John Clare--psychoanalysis emerges as a multi-authored autobiography. Its subjects are love, loss, and memory; its authors are the analyst and the analysand, as well as the several selves brought to life in the process. A passionate and delightfully playful defense of the virtues of being uncommitted, On Flirtation sets before us the virtue of a yet deeper commitment to the openendedness of our life stories.