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In the context of the project" WeNet: Internet of us" we are studying the role of diversity in relation to Internet-mediated social interactions. In this paper, in particular, we analyze a possible relationship between personality aspects and social interaction mediated by digital platforms. More specifically, we rely on the five personality traits (Extraversion, Agreeableness, Conscientiousness, Emotional Stability and Openness to Experience), commonly referred to as" Big-five", and associate them to automatically extracted behavioral characteristics derived from the experience of using a Chatbot for a closed community of students at the Universidad Católica" Nuestra Señora de la Asunción"(UC). The personality data comes from a self-report made by the users through questionnaires. According to a survey to the participants, overall the results show very positive appraisals about the use of the Chatbot in terms of user experience and its main functionalities, which is very encouraging for future pilots. As for the role of personality in relation to the main use of the Chatbot, although further experience is required to confirm trends, the results suggest that the Big-five personality traits are to some extent correlated with: the active participation (Agreeableness and Openess); the type of contribution in term of length of questions/requests for help and answers (Agreeableness, Neuroticism and Openness); and, the network of interactions evolution over time (Openness and Neuroticism).