Despite strains created by massification and the managerialist agenda driving higher education, academics manage to stay productive and to get on with their students. However, the workaday intimacy between students and teachers can get lost so that personal contact with students, which for many years has been a hallmark of university life, has become something to be avoided and has been identified as ‘nostalgic’ and linked to outdated ‘elite manners’ (Scott, 1995; Smith & Todd, 2005). Alternative approaches have sprung up to deal with increases in student numbers: disembodied forms of learning such as electronic interactive courses, distance learning, and lectures to enormous groups of anonymous students. Meanwhile self-reflection has been promoted as a way for lecturers to monitor and enhance their practice. Furthermore, there is growing anxiety about the risks involved in relationships to students as exemplified in the film, Oleanna, written and directed by David Mamet (1994). This paper argues that in the film both teacher and student are steeped in unconscious fantasies of what their role involves that prevent either from functioning to achieve the core educational task: he of teaching his subject, she of learning about it, and the film ends in an orgy of emotional and physical violence. Neither party can sustain a view of their own actions and beliefs from ‘outside’. The capacity to entertain a view of ourselves that is distinct from our own view is a product of having successfully negotiated the Oedipus complex and the prohibition it represents in relation to the parental couple. If we can accept our own position and partiality we may develop the benefit of being able to occupy ‘triangular space’ (Britton, 1998, p. 42). In Oleanna, the student and teacher repeatedly misunderstand each other, a process which escalates and drives the film to its terrible concluding scene of violent schism when both parties are exposed to their own subjective experience and understanding being eliminated. This amounts to what Britton identifies as the annihilation of ‘self-established meaning’, which brings about primordial chaos. The paper suggests that while reductions in personal contact between students and teachers may provide a solution to problems of risk and workload, they may also reduce the opportunity for teachers to develop, through personal contact and dialogue, a greater and more realistic understanding of themselves and their task, than may be achieved by teacher self-reflection alone.