This case report describes a series of conflicts centering on gender issues at a large metropolitan high school. The case is accompanied by discussion questions designed to present prospective teachers with complex professional problems, asking them to interpret the situation and decide upon possible solutions. The report was written to develop teaching students' abilities to spot issues and frame problems as a new teacher in a highly factionalized school environment. The case opens with a confrontation between a senior student, Jeanne Campbell, and school vice principal Frank Leyden. According to Jeanne, Leyden told her that young women who dressed provocatively were "asking for it" when she suggested that he sponsor a rape awareness workshop. The vice principal asserts that Jeanne had misinterpreted his remarks. Austin Nickerson, a new English teacher, is asked to witness the confrontation and must make a public statement about the meeting when Jeanne's parents consider bringing suit against Leyden. Nickerson is also witness to a host of other gender-related problems involving students, faculty, and administration at the school. Questions following the case report encourage extensive discussion regarding the high school staff's responses to gender-related problems both in the school at large and in the classroom. Two exercises ask teaching students to analyze Nickerson's reading requirements and assess his classroom techniques for possible gender bias. The case is based on authentic occurrences at a large urban high school, but names and identifying details have been changed to protect confidentiality. (TES)