In most western cultures, parents are concerned about children who seem to be shy. They worry about the child’s social adjustment, and the implications that the child’s shyness might have for the future. Developmentalists, as well, consider interactions with peers necessary to normal social development, and they usually consider shy or socially withdrawn behaviour an obstacle to normal development (Dodge, 1986; Rubin and Rose-Krasnor, 1992; Rubin and Stewart, 1996; Rubin, Stewart and Coplan, 1995; Selman, 1985). In this chapter, I look at whether these notions are supported when a long-term perspective is taken. Using data from a birth-to-midlife study, I examine the links between childhood shyness and middle adulthood adjustment.