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This study uses a qualitative and longitudinal research design to investigate how parents from a range of social, economic, racial, ethnic, linguistic and geographic locations and identities arrived at their middle school preferences in a Brooklyn district that requires choice at the middle school level. I found that all participants actively “shopped” for schools for their children, in that they all sought a good “fit,” however defined. Yet all participants also confronted too many unknowns to confidently identify which school would ultimately offer the “best” educational experiences for their child. Thus parents relied on a combination of “word on the street” and advice from individuals whose views they trusted to help develop their preferences and guide their school rankings.