This qualitative study applied a life course framework to characterize the nature of interpersonal partner relationships of Mexican American young adult men affiliated with street gangs during their adolescence. Data come from a 15-year longitudinal mixed-method cohort study conducted in San Antonio, Texas. We analyzed semi-structured interviews conducted with a subsample (n = 40) during the course of three face-to-face sessions to explore the men's motivations, aspirations, and goals to lead conventional lives, despite their criminal justice involvement. Specifically, we focus on the complex nature of maintaining ties to children, the navigation of complicated family structures, the processes of seeking partners with economic resources, and on partnerships with criminal and delinquent partners. We document the complex interpersonal nature of these relationships as men contend with serial incarceration and their desires and motivations to desist from criminal behavior.