The relationship between victimization and offending has been shown consistently across different samples, settings, and crime types. This study uses data from the Pathways to Desistance Study to examine dual trajectories of offending between the ages of 15 and 24 in a sample of male felony offenders. The dual trajectory models demonstrate substantial convergence in victimization and offending. And while there are sizable numbers of youth who continue to be victimized, but desist or decrease in their offending behaviors, very few youth continue to offend in the absence of continued victimization. This study also proposes and tests three criminological theories that have been employed as explanations for the victim-offender overlap—low self-control, lifestyles/routine activities, and street-code attitudes. The logistic regression results indicate that involvement in risky and/or unstructured, unsupervised activities is a key correlate of the victim-offender overlap. The strength of the relationship between routine activity variables and the victim-offender overlap supports the provision of structured, supervised activities for youth and young adults as a way of preventing future victimization and offending, particularly among youth who have high exposure to violence.