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A scientific understanding of emotion experience requires information on the contexts in which the emotion is induced. Moreover, as one of the primary functions of music is to regulate the listener's mood, the individual's short-term music preference may reveal the emotional state of the individual. In light of these observations, this paper presents the first scientific study that exploits the online repository of social data to investigate the connections between a blogger's emotional state, user context manifested in the blog articles, and the content of the music titles the blogger attached to the post. A number of computational models are developed to evaluate the accuracy of different content or context cues in predicting emotional state, using 40,000 pieces of music listening records collected from the social blogging website LiveJournal. Our study shows that it is feasible to computationally model the latent structure underlying music listening and mood regulation. The average area under the receiver operating characteristic curve (AUC) for the content-based and context-based models attains 0.5462 and 0.6851, respectively. The association among user mood, music emotion, and individual's personality is also identified.