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Background: The relationship between generalised anxiety disorder (GAD) and alexithymia has been poorly studied in adolescents. The present study examined the alexithymia levels in adolescents with GAD and their parents compared with healthy control participants (adolescents and their parents). Method: The sample included 300 participants: 50 adolescents with GAD and 50 healthy adolescents, 13–18 years of age, and their 200 parents (100 mothers and 100 fathers). The Schedule for Affective Disorders and Schizophrenia for School-Age Children was performed to evaluate adolescents’ mental health while the 20-item Toronto Alexithymia Scale was performed to assess alexithymia levels in both adolescents and their parents. Results: Adolescents with GAD showed a significantly higher rate of alexithymia when compared with control adolescents. The mothers of adolescents with GAD showed an alexithymia score higher than did the controls’ mothers. The fathers of the two groups showed no differences of in their rate of alexithymia. Moreover, in the clinical sample, adolescent and maternal alexithymia scores were not correlated, while significant directed correlations were found between these adolescents and their own fathers. Conclusions: Our findings show an association between GAD and alexithymia in adolescents. A significant presence of alexithymic traits in the mothers of the patients with GAD was shown. An intergenerational transmission of alexithymia could be supposed but this cannot be a linear mechanism. The assessment of alexithymia in adolescents with psychological disorders, and in their parents, could be useful to plan a more targeted therapeutic approach.