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Runaway youth often face a multitude of negative experiences during their childhood, which often leads to trajectories of psychological disorder/distress, victimization, and offending. This propensity for negative life trajectories may be exacerbated by repetitive runaway behavior. Additionally, these negatives experiences may be further shaped by the gender of the youth, thus creating distinct gendered pathways to chronic runaway behavior, victimization, and offending. This study utilized a sample of youth runaways in the state of Florida (N=295) to build upon the classification/typology research on juvenile runaways by assessing the presence of latent groups of youth based on runaway frequency. In addition, this study utilized classical and modern criminology theories to influence the assessment of the relationship between known runaway risk factors and chronic runaway status. Group-based trajectory modeling was performed and two distinct groups of youth runaways were identified for both full and gender-exclusive models. Chronic runaway analyses indicated both unique and similar gender-based relationships between chronic runaway status and relevant risk factors, suggesting partial support for a gender specific theoretical perspective. Results provide additional insight into youth runaway behavior while also suggesting the need for further exploration of chronic runaway status within the youth runaway population.