The present study explored social and emotional loneliness, and victimisation among a sample of adult male prisoners. 241 prisoners took part, completing a behavioural measure of behaviours indicative of bullying (DIPC-R: Direct and Indirect Prisoner behaviour Checklist, Ireland, J.L. 2003. The Direct and Indirect Prisoner behaviour Checklist -- Revised. Psychology Department, University of Central Lancashire). and a measure of social and emotional loneliness (SELSA: Social and Emotional Loneliness Scale for Adults, DiTommaso, E. & Spinner, B. (1993). The development and initial validation of the social and emotional loneliness scale for adults (SELSA). Personality and Individual Differences, 14, 127-134.). Differences between the groups involved in bullying (i.e. pure bullies, pure victims, bully/victims and those not involved) were noted, with victim groups (pure victims and bully/victims) presenting with higher levels of social loneliness than those not-involved. Emotional loneliness was not a distinguishing characteristic for membership to the pure victim or bully/victim group, and instead was found to be associated with the type and amount of victimisation reported: victims who reported multiple types of victimisation presented with higher levels of emotional (family) loneliness than victims reporting just one type of victimisation. Increased victimisation was also associated with increased levels of social and emotional loneliness, most notably with regards to indirect victimisation. The results are discussed with reference to the environment in which the victimisation is taking place, and we outline a potential application of life events and added stress models in understanding social maladjustment (loneliness) among prisoners.