Objectives: Phobic anxiety disorders generally breed true. In this regard, family studies have suggested an association between childhood shyness and maternal social phobia. In this study, the relationship between childhood shyness and maternal social anxiety was examined. Subjects and Methods: 203 5-year-old children from an Arabian Gulf community and their mothers were evaluated. The children were assessed in stage 1 using the shyness scale of Stevenson-Hinde and Glover and the Preschool Behavior Checklist (PBCL), while mothers completed the Liebowitz Social Anxiety Scale. In the second stage, blind clinical interviews were carried out to ascertain the diagnosis of psychiatric diagnoses, if any, using DSM-IV criteria. Results: 27% of the children were identified as shy using the shyness scale of Stevenson-Hinde and Glover and 19% scored above the cutoff for behavioral disturbance on the PBCL. Child shyness was associated with female gender and maternal social anxiety as indicated by scores on the Liebowitz Social Anxiety Scale, while an inverse relationship was noted with behavioral disturbance. The odds of the child having a high shyness score was increased if the mother had social anxiety (odds ratio = 2.14) and the child lived in a family that was ‘not socially active’ (odds ratio = 1.42). Conclusion: Our initial findings suggest that there may be a complex interaction between maternal social anxiety and family sociability in childhood shyness. Prospective longitudinal work is indicated.