||I intend to examine the sources Bernard Shaw uses to reconfigure family structures in his play You Never Can Tell (1895). I will argue that Shaw employs characters who induce pain and offer comfort to adjust the family structure into a viable support unit. Although several of Shaw's other plays explore family, this play is unique in its primary focus on family. The fact that this play exactly mirrors Shaw's own family while he was growing up---estranged parents with two daughters and a son---serves to reinforce this play's concern with family dynamics. Very little critical work exists that focuses solely on You Never Can Tell , but the play offers a rich source for literary inquiry. My initial chapter will explore the relationship between Oscar Wilde's The Importance of Being Earnest and Shaw's You Never Can Tell . I will show how Wilde and Shaw, while sharing a classic comic structure and a focus on familial structures, depart in their concept of family and its function in late Victorian society. I will then show that Shaw accomplishes the restructuring of this family through two professional characters. The first, a dentist named Dr. Valentine, induces pain to force the family into a new proximity with one another. The necessity to assuage the pain opens the play to entrance of Walter Boon, a good-natured waiter who eases the tensions between the family members with attentive service. Viewed in the dramatic traditions of New Comedy, the literary context of Shaw's rivalry with Wilde, and the social changes of the late Victorian period, Shaw's play offers a fertile text for the exploration of family dynamics.