The decline and delay of marriage has prolonged adolescence and the transition to adulthood, and consequently fostered greater romantic relationship fluidity during a stage of the life course that is pivotal for both development and offending. Yet, despite a growing literature of the consequences of romantic relationships breakup, little is known about its connection with crime, especially among youth enmeshed in the criminal justice system. This article addresses this gap by examining the effects of relationship breakup on crime among justice-involved youth—a key policy-relevant group. We refer to data from the Pathways to Desistance Study, a longitudinal study of 1354 (14 % female) adjudicated youth from the juvenile and adult court systems in Phoenix and Philadelphia, to assess the nature and complexity of this association. In general, our results support prior evidence of breakup’s criminogenic influence. Specifically, they suggest that relationship breakup’s effect on crime is particularly acute among this at-risk sample, contingent upon post-breakup relationship transitions, and more pronounced for relationships that involve cohabitation. Our results also extend prior work by demonstrating that breakup is attenuated by changes in psychosocial characteristics and peer associations/exposure. We close with a discussion of our findings, their policy implications, and what they mean for research on relationships and crime among serious adolescent offenders moving forward.