Shyness is not unlike many psychological constructs in that it connotes a rich cluster of behaviours, cognitions, feelings and bodily reactions. But when adolescents' shyness creates keen sensitivity to cues of being rejected, preventing them from speaking up for their rights and expressing their own opinions, thereby encouraging self-consciousness and excessive preoccupation with their emotions, it becomes a problem for both these adolescents and their surroundings. This paper presents 10 adolescents' experiences of being shy in a school context to such a degree that it is regarded as being a behavioural and emotional problem. In light of elements from an existential-phenomenological understanding, challenges and remedial measures for these adolescents as well as their peers and teachers are discussed. Finally, focus will be placed on how teachers can promote good relationships and working environments and in this manner prevent shyness from becoming a behavioural and emotional problem in school.