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 of the 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. (Contains 1 table.)