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The study aims to examine the issue of the relationship between Emotional stability, one of the fundamental personality determinants, and users’ Risk Averseness, on the one hand, and user behavior in the field of e-Commerce, on the other hand. In the beginning, a brief overview of today’s primary benchmark for the measurement of human personality – the Big Five Model is proposed. A study with 226 participants has been conducted for the aim of the research, based on the TIPI test. The TIPI test is a validated and abridged version of the Five-Factor model. The result of the conducted survey confirms the existence of significant relationships between personality determinant Emotional stability and consumer’s Risk awareness, on one side, and some of the observed main functionalities of the online stores, on the other side. Two regression models of the field of Machine Learning (Linear Regression and Random Forest) have been implemented to make a reliable forecast about the user’s preferences in the process of online shopping. The conclusions made rely on the obtained results and analysis.