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 Catolica "Nuestra Senora de la Asuncion" (UC). The personality data comes from a self-report made by the users through questionnaires. The main results show very positive appraisals about the use of the Chatbot in terms of user experience and its main functionalities. 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 there are some correlations between some of the five personality traits and the length of questions and answers as well as the selection of best answers.