Acceptance of gay, lesbian, bisexual, transgender, and queer (GLBTQ) adolescents in high schools is growing. Yet, the experience of this family suggests that creating and maintaining a safe environment for GLBTQ students requires constant vigilance, even in the best of environments. As school administrators face competing pressures from stakeholders, GLBTQ advocacy is often left to the students, unlike other types of diversity advocacy based on race, culture, or gender. This case describes how one family chose a "safe" school and struggles to keep it so. The case challenges education administration students to experience school through the eyes of a young man who is gay, and his family, and to determine what is adequate student support.