The purpose of this research is two-fold: (a) to explore the relationship between the listeners’ personality trait, i.e., extraverts and introverts and their preferred music genres, and (b) to predict the personality trait of potential listeners on the basis of a musical excerpt by employing several classification algorithms. We assume that this may help match songs according to the listener’s personality in social music networks. First, an Internet survey was built, in which the respondents identify themselves as extraverts or introverts according to the given definitions. Their task was to listen to music excerpts that belong to several music genres and choose the ones they like. Next, music samples were parameterized. Two parametrization schemes were employed for that purpose, i.e., low-level MIRtoolbox parameters (MIRTbx) and variational autoencoder neural network-based, which automatically extract parameters of musical excerpts. The prediction of a personality type was performed employing four baseline algorithms, i.e., support vector machine (SVM), k-nearest neighbors (k-NN), random forest (RF), and naïve Bayes (NB). The best results were obtained by the SVM classifier. The results of these analyses led to the conclusion that musical excerpt features derived from the autoencoder were, in general, more likely to carry useful information associated with the personality of the listeners than the low-level parameters derived from the signal analysis. We also found that training of the autoencoders on sets of musical pieces which contain genres other than ones employed in the subjective tests did not affect the accuracy of the classifiers predicting the personalities of the survey participants.