This study investigated the relation between friendship, loneliness and depressive symptoms in adolescents with Asperger's Syndrome (AS). Thirty-five adolescents with AS and 35 controls matched on chronological age, school year and gender distribution, completed questionnaires designed to ascertain the quality of their best-friendship, motivation for developing friendships, feelings of loneliness and depressive symptomatology. Relative to the comparison group, the participants with AS reported poorer quality of best-friendship and less motivation to develop friendships. The individuals with AS displayed higher levels of loneliness and depressive symptoms, with loneliness being negatively correlated with the quality of their best-friendship. Increased levels of loneliness in the adolescents with AS was predicted by the extent to which their best-friendships were characterized by high levels of conflict/betrayal. Increased depressive symptoms in the adolescents with AS were also predicted by this factor. The findings indicate that increased levels of negative affect may be related to the poor quality of social relationships often reported in this population.