In most Western societies today, where boldness and good self- esteem are valued, socially fearful behaviors are viewed as a disadvantage. During adolescence, social participation requires a good deal of self-confidence and social skills, specifically when it comes to acquiring and spending time with friends, getting romantically involved, or having meaningful relationships with parents. Adolescents go through a number of physical and emotional changes that make them highly vulnerable for developing shyness. The effects of shyness on social relationships in adolescence and vice versa have, nonetheless, been relatively understudied. This dissertation provides some insights into the lives of shy early adolescents, showing that both peers and parents may affect shyness in several negative ways. The shy adolescents were also found to be active agents in their own lives, as their social fears were influential in their relationships. On a more positive note, shyness was protective against involvement in problem behavior. Even though certain elements of adolescent shyness can make it unfavorable for the individual, there are also reasons to appreciate its distinctiveness.