Restrictions on boys’ capacities to process and to show emotion, however detrimental for their development, constitutes a key lesson of the masculinity curriculum learned in schools. To explore what schools can do to offer support for boys’ resistance to this curriculum, a series of studies has been conducted at a suburban independent school outside Philadelphia, PA. The present study uses a mixed-method design, including teachers, university-based researchers and students on the research team, to examine how boys’ participation in a peer counseling program influenced their sense of self and self-expression. A survey, focus groups, interviews, and observations supported the usefulness of the intervention for boys. The following qualitative themes emerged: (1) The constraining effect of the school’s masculinity culture on boys’ emotional development; (2) the value of a “safe space” in overcoming this culture and in promoting boys’ learning and connection; (3) boys’ ready development of new skills, especially in relation to emotional experiences, when invited to do so; (4) the deepening and broadening of boys’ friendships resulting from their self-disclosure and mutual support.