Background: School choice models assume that parents and children have varied educational preferences and that catering to those preferences will result in superior educational experiences for all. Yet, we still know relatively little about how parents identify the best school “fit” for their children and families. This question is particularly important in the context of gentrifying urban districts, where school choice often serves to broaden and intensify school segregation at precisely the moment in which racial, ethnic, and socioeconomic school integration could be a real possibility. Objective: The purpose of this study was to better understand how parents determined the best school fit for their children within a competitive system of public school choice. Setting: The study was conducted in a diverse school district in Brooklyn, New York, in which families were required to rank their preferred middle schools and schools were required to rank interested students. This competitive choice model has the potential to match students and schools by educational fit when top choices align, but can also lead to greater academic stratification and racial, ethnic, and socioeconomic segregation. Participants and Research Design: Twenty-six parents from a range of social, economic, racial, ethnic, linguistic, and geographic locations and identities were interviewed over a 15-month period before, during, and after applying to middle schools for their children. The study’s longitudinal design captured parents’ shifting priorities, perceptions of school options, and notions of fit across time. Findings: Study participants’ school preferences shifted through time and were often constructed collectively. Parents sought out and accessed information about their options but, faced with too many uncertainties, also turned to others for guidance and assurance. Race, ethnicity, and class often informed parents’ perceptions of schools, but not uniformly. Notions of fit varied both within and across groups, and at times parents with similar backgrounds and stated educational priorities arrived at disparate school preferences based largely on perceptions constructed within their social networks. Conclusion/Recommendations: These findings suggest that offering families expanded access to and better quality information about their school options will do little to reduce the segregating effects of choice without also ensuring that schools are organized to address the diverse needs of students and families. Seeking to make all schools inclusive and pedagogically responsive to diverse learners will decrease some of the market efficiencies school choice has promised to deliver, but may offer an even greater social good by advancing the goals of integrated and equitable schooling.