This study compared levels of emotional loneliness between sexual murderers and rapists who had not gone on to kill their victim/s. All participants were life-sentenced prisoners in the United Kingdom. Assessment consisted of a semistructured interview and was subjected to grounded theory analysis. This approach is defined as the breaking down, naming, comparing, and categorizing of data. As such, it is distinguished from other qualitative methods by the process of constant comparison. This continual sifting and comparing elements assists in promoting conceptual and theoretical development. The results of this process found that sexual murderers, compared to rapists, reported significantly higher levels of grievance towards females in childhood, significantly higher levels of peer group loneliness in adolescence, and significantly higher levels of self as victim in adulthood.