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Using emerging adulthood as an overarching theme, this research study examines the life and offending of transient adult males using qualitative grounded theory analysis. Through the analysis of in-depth interviews, young homeless men experience a pathway to homelessness and offending through forced adulthood and the breaking of social bonds. After their bonds to society are weakened they exhibit a cycle of substance addiction and offending. With little social capital as a result, they have limited pathways out of their street-based lifestyle. The qualitative evidence provides a framework suggesting a pathway out of offending, homelessness, and drug abuse through the restoration of prosocial bonds.