Developmental changes in adolescents' relationships with parents and friends intertwine, but individual differences in these relationships are likely to emerge as not all adolescents develop similarly. Generalized anxiety symptoms may underlie these individual differences, as these symptoms have frequently been associated with interpersonal difficulties. This study examines relationship quality development with parents and friends in adolescents with low and high levels of generalized anxiety symptoms. A latent transition analysis was performed in a two-cohort five-wave study design covering ages 12 to 16 (n = 923, 50.8% males) and 16 to 20 (n = 390, 43.4% males). About one-third of adolescents with high levels of generalized anxiety symptoms perceived a turbulent relationship with both their parents and best friends, whereas only one-tenth of those with low levels of generalized anxiety symptoms did. Low levels as opposed to high levels of generalized anxiety symptoms predicted a twice as high likelihood to perceive harmonious relationships with both their parents and best friends. Nevertheless, adolescents with low and high levels of generalized anxiety symptoms exhibited similar trends in relationship development. Overall, our findings indicate that generalized anxiety symptoms are not deterministic markers for relationship difficulties as there were plenty of adolescents with high levels of generalized anxiety symptoms that experienced no relationship difficulties across adolescence.