This article explores how choral directors negotiate personal and professional identity in relation to gender discourse. Many music teachers have tried hypermasculine messages, such as "Real men sing," used as recruitment tools for getting adolescent boys to join choir. Designed to counter the perception that "singing is for sissies," these messages reinforce limited views of masculinity that can present a problem for choral directors. Gay male teachers especially may feel obligated to divide aspects of their personal identity from their professional identity for the benefit of male involvement in their program. Given these circumstances, the question of what defines a man as "real" must be considered within the context of gender, gender performance, sexuality, and teacher identity.