The purpose of this study was to explore street youths' life histories to assess how early negative experiences (e.g., maltreatment) contributed to alternative developmental paths marked by emotional and behavioural difficulties. Ten male and female participants responded to an attachment questionnaire and told their life stories. The data were analyzed using qualitative and quantitative techniques. The results showed that both groups experienced difficulties in attaining educational, employment and relational successes. However, differences were found between gender groups in views of self, with females often describing themselves as victims whereas males' views were often characterized by self-efficacy stemming from successful completion of criminal or violent acts – in other words, as victimizers. Finally, it was found that males were more able to apply developmental advanced interpretations to their life experiences.