The title of this chapter is doing some work, albeit in a somewhat awkward fashion. Giles Deleuze appears, philosopher of a “bastard kind” (Massumi 1992, 1). Deleuze opens the work because he, and his concepts, do something they are rather good at: a bit of troubling, a bit of “prying open” of habitual ways of thinking (Massumi 1987, xv). In this chapter that bit of troubling and prying open is directed toward a rethinking of youth transition and the role of schools in that particular form of ‘becoming’. Teenage mothers appear as they, too, are ‘known’ to be trouble makers: the ‘teenage mother’ signifier is by default a negative one. As Sara found, ‘teenage mother’ as a signifier doesn’t rest easily alongside ‘school girl’ as a signifier. It is this assemblage of teenager+parent+school student — a gathering in which I too was once involved (Kamp and Kelly forthcoming) — that is the focus of this chapter.