Youth who hold negative attitudes toward the justice system are more likely to engage in crime. It is particularly important to study attitudes early in someone’s criminal career when they may still be open to change. To date, however, there has been no empirical test assessing whether the relation between attitudes and behavior changes after a first arrest. Using a sample of 1,216 first-time, male, juvenile offenders from the Crossroads Study, the present study explored: (a) racial/ethnic differences in the longitudinal patterns of youths’ attitudes; and (b) reciprocal associations between youths’ attitudes and both their offending behavior and rearrests in the 2.5 years after their first arrest. The results indicated that White youths’ attitudes remained largely stable, Black youths’ attitudes became more negative, and Latino youths’ attitudes became more negative but only among Latino youth who reoffended. Although the results indicated that youths’ attitudes were related to both offending and rearrest, the bidirectional relation between attitudes and offending weakened across time. After 2.5 years after their first arrest, attitudes no longer predicted offending or rearrests. These novel findings suggest that a youth’s first contact is likely the most impactful. When it comes to young offenders’ interactions with the justice system, first impressions matter.