This study examined the relationship between "theory of mind" and attachment-related anxiety and avoidance in adolescence. The "Reading the Mind in the Eyes" test and the "Experiences in Close Relationships--Relationship Structures" questionnaires were administered to 402 14-19 year-old adolescents. Contrary to expectations, anxiety but not avoidance with mother was associated with less accurate mindreading, and this effect was stronger in younger than in older adolescents. Results might be explained in terms of the inconsistency of caregiver behavior that is supposed to cause anxious strategies, and thus illustrate the need to consider not only the effects, but also the causes of different types of insecure strategies. (Contains 4 tables.)