The stories of three high school boys about their experiences in school-based choral music provide the framework for a discussion of the role music educators can play in retaining male singers. The “possible selves” construct (Markus & Nurius, 1986) is explored alongside research-based implications about specific steps toward developing boys’ identities as choral musicians. Possible selves are future conceptions of the self that are either positive (hoped-for) or negative (feared). The changing adolescent male voice occurs at approximately the same time as major social, academic, and other physical changes. It is thought that these issues coincide in a manner that discourages boys from participation in choral music (Freer, 2007). Drawing upon a successful non-musical model, the author proposes a variant of the “Possible Selves Program” (Hock, Deshler, & Schumaker, 2006) for use in music settings.