In this thesis I explored the experiences of four pairs of mentors and mentees who were part of a mentoring programme aimed at reducing truancy. I used in-depth interviews to gain insight into the complexity of mentoring relationships within this particular setting. The central focus of this work was to understand more about the processes of the relationship that occurred between mentors and mentees and the way the experience is made sense of by them. The findings suggest that factors such as the inherent assumptions of the programme, the expectations of the mentors and the responses of the mentees impact on feelings of satisfaction for mentors and the potential for developmental growth for mentees. I used the results of this study along with the current literature as a starting point to critique the underlying assumptions of this particular programme, to question the nature of successful mentoring and to explore the usefulness of socio-cultural theory as a perspective to add to our understanding of relationship dynamics within mentoring relationships. I suggest that this programme's use of 'friendship' as a method of encouraging developmental relationships that impacted on truancy left mentors under prepared for their role and feeling confused. I draw on socio-cultural perspectives to suggest that relationship dynamics like negotiation, joint engagement and participation in activity are useful ways to encourage developmental mentoring relationships within programme settings.