In this study, we investigated whether parental smoking-specific communication is related to adolescents’ friendship-selection processes. Furthermore, we investigated whether adolescents and their best friends influence each other over time, and what role parents play in this process. In the present study we used data from the Family and Health project in which at baseline 428 full families participated. In this 2-year, three-wave longitudinal study data were available from fathers, mothers, early adolescents (aged M = 13.4 years, SD = .50), and middle adolescents (aged M = 15.2 years, SD = .60). The majority of the participating adolescents were of Dutch origin (>95%). There was an almost equal distribution of boys and girls, and adolescents with lower, middle, and higher educational levels were equally represented. Analyses were conducted by means of Structural Equation Modeling. Results demonstrate that a high quality of the smoking-specific communication is related to a lower likelihood of adolescent smoking, whereas the frequency is positively associated with adolescent smoking. Both the quality and frequency of parental smoking-specific communication were related to adolescents’ selective affiliation with (non-)smoking friends. The findings suggest that parental smoking-specific communication is associated with adolescent smoking directly but also indirectly by influencing the friends the adolescents will associate with.