Ever since the field of intelligent tutoring began to develop, one of its main purposes has been to create a personalized learning environment to imitate one-to-one interaction between a student and a human-tutor. Although there have been a significant progress towards achieving this goal both from methodological and affective point of view, current systems are not truly adaptive to a student. It is believed that one of reasons for that is the lack of system’s personalization itself, and particularly through its representation to user - virtual tutor. To close this gap, it is proposed to generate tutor’s personality based on user’s personality. The paper introduces steps of personality modeling for such system as well as tutor’s personality generation. This enables creating an attractive virtual tutor that serves for a common goal of the research - truly adaptive intelligent tutoring system.