This study examined to what extent adolescents’ and their friends’ risk behaviors (i.e., delinquency and alcohol use) hinder or promote their academic achievement (grade point average [GPA]), and vice versa. Longitudinal data were used (N = 1,219 seventh- to ninth-grade adolescents; Mage = 13.69). Results showed that risk behaviors negatively affected adolescents’ GPA, whereas GPA protected against engaging in risk behaviors. Moreover, adolescents tended to select friends who have similar behaviors and friends’ behaviors became more similar over time (same-behavior selection and influence). Furthermore, although same-behavior effects seemed to dominate, evidence was found for some cross-behavior selection effects and a tendency in seventh grade for cross-behavior influence effects. Concluding, it is important to investigate the interplay between different behaviors with longitudinal social network analysis.