While Facebook, the world’s most popular Social Networking Site (SNS), has been warmly welcomed by many commentators and practitioners within the educational community, its effects, impacts and implications arguably remain insufficiently understood. Through the provision of an anecdotal and experiential account of the authors’ attempt to introduce Facebook into an existing Peer Assisted Study Sessions (PASS) student peer mentoring program at Victoria University (VU) in Melbourne, this paper aims to explore and thereby explicate some of the issues inevitably arising in relation to the adoption and utilisation of social networking technologies in educational settings. While the authors’ experiences of their own ‘Facebook experiment’ were somewhat ambiguous and ambivalent, this paper is intended to contribute to the ever-expanding body of literature concerned with the use of Facebook in education and to thereby assist in improving educators’ requisite understanding of both the potential positives and pitfalls involved. On the basis of the authors’ experience, it is suggested that careful consideration as well as explicit and iterative articulation and negotiation surrounding issues of staff and student expectations, boundaries and identity management in an online environment comprise the minimum requirements for the successful implementation of social networking into student peer mentoring programs.