There has always been a dilemma whether introvert students enjoy role play activity, since it is widely regarded as too exposing for introvert character. Consequently, do extrovert students necessarily enjoy such activity more? The aim of this paper was to examine whether there is a potential correlation between students’ type of personality, in terms of extroversion, and the extent of their enjoyment with role playing. A randomly chosen group of 31 philology course students, aged 16–18, mainly female, were assessed with the NEO PI-R personality test (Extroversion subscale) and a self-report questionnaire on role play. To sum up, we will conclude that in some instances the personality factor prevails, whereas in some others, other factors, such as good rapport, take their dominance. Thus, it is up to an individual teacher to provide a safe environment and get their students accustomed to role play.