Some critics say that in most road movies, elderlies represent stability and tradition. However, the lives of two old widowers in "About Schmidt" (2002) and "Everybody's Fine" (2009), tell the viewers to reexamine the patriarchal family structure and to move beyond the sex roles and crossover their roles successfully in our later lives. In the movies, the fathers are the bread winners and the mothers are the homemakers. Traditional sex-roles are observed in both of these families. The mothers act as the mediators between children and their busy fathers. Therefore, when the mothers are gone, the fathers and the children are faced with difficulties in communicating with each other. Being retired, fathers also lose connections with their social lives. As a result, they experience social marginalization which has a devastating impact on their self-esteem. Betty Friedan suggests if people hold on to the conventional sex roles, they would be thrown into crisis in their later years when they experience various changes in their lives. She suggests men and women should move beyond the gender line and make a crossover. By looking at the two road movies the paper examines how crossover helps the widowers reunite with their families and regain their homes.