After James nearly starts a deadly fire, Doug must face his father's senility. Buddy encourages James to live with the family instead of going to a nursing home.
Doug sees a specialist after having chest pains, but an argument erupts between him and Willie about him and Rachel going to Mexico. Meanwhile, Buddy invites the school janitor home for Christmas, much to the reluctance of Kate.
Just as Nancy and Buddy finally affect a closer sister relationship, Buddy develops a crush on her jogging partner Jack and later discovers that he and Nancy have been intimate.
Kate's unplanned pregnancy is a source of conflict and embarrassment in the family. Buddy's friend Erica wants to lose her virginity and selects Willie as her partner.
Buddy's friendship with a teacher leads to whispers at school and a valuable lesson for Buddy about good people doing bad things. Meanwhile, Annie will do anything to persuade Willie to grant her an interview for her school newspaper.
Willie finds himself torn between two loves after he falls for the director of his play just before announcing his engagement to Rachel. Doug objects to Buddy's plans to buy a questionable used car.
Buddy criticizes Kate's nerdy piano student but later views him in a different light. Nancy needs Annie to teach her how to roller skate in order to impress a handsome colleague.
Buddy pretends that her college applications were rejected, but her real issue is being Willie Lawrence's little sister. Doug attempts to share his passion for baseball with Annie.