Shyness, feelings of uneasiness or hesitation when faced with a novel or unfamiliar social situation, in early childhood has been found to be a risk factor for social difficulties later in life. When combined with fitting parenting, however, outcomes of shyness can be less detrimental. The present study examined the joint effects of children’s shyness and mothers’ and fathers’ parenting on the development of children’s pro-social behaviors during early schooling years. A total of 200 children were rated by their parents on their shyness at age 3 and on their pro-social behaviors at ages 4, 5, 6, 8, and 9. The children’s mothers (n = 185) and fathers (n = 175) completed questionnaires measuring their levels of affection and behavioral control when the children were four years old. The results of the Latent Growth Curve modeling showed that, although maternal and parental affection were related to high levels of pro-social behavior for both shy and non-shy children, shy children, in particular, benefitted from parental affection in terms of their subsequent development of pro-social behaviors. The results further showed that paternal behavioral control was positively associated with pro-social behavioral levels among non-shy children only.