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Location sharing is a particularly sensitive type of online information disclosure. To explain this behavior, we compared the effectiveness of using self-report measures drawn from the literature, behavioral data collected from mobile phones, and a new type of measure that represents a hybrid of self-report and behavioral data to contextualize users’ attitudes toward their past location sharing behaviors. This new measure was based on a reflective learning paradigm, where one reflects on past behavior to inform future behavior. Based on a study of Android smartphone users (N=114), we found that the construct ‘FYI About Myself’ and our new reflective measure of one’s comfort with sharing location with apps on the smartphone were the best predictors of location sharing behavior. Surprisingly, Behavioral Intention, a commonly used proxy for actual behavior, was not a significant predictor. These results have important implications for privacy research and designing systems to meet users’ location sharing privacy needs.