In this qualitative study, the authors examine the advisory program of a Horizon Schools to Watch middle grades school. Horizon Schools to Watch is the Illinois affiliate of the National Forum to Accelerate Middle School Reform national Schools to Watch (STW) program, meaning schools with the STW designation have made significant inroads in implementing exemplary middle school practice. This advisory program is unique in that girls and boys are separated by gender during the advisory time. Using focus group interviews of the middle grades students and their teaching teams for data gathering purposes, the authors explore issues related to the impact that gender separation has on establishing trust, openness and confidentiality within the advisory program. The findings suggest that gender separation appears to provide benefits in the eyes of the students and teachers, making the advisory program a key component in helping to provide an effective middle school environment.