Joan Gallagher (Joan Cusack) is a high school teacher who is proposed to by her boyfriend, Jake Evans (Kyle Chandler), after only six weeks. Jake is ready to commit, but Joan, confused and shocked, wants to take the relationship more slowly.
Joan's friend, a music teacher at the high school, is Betsy Morgan (Jessica Hecht). She's recently married Mark Ludlow (Wallace Langham), also a teacher. Joan and Betsy often turn to their mutual friend Dr. Ruby Stern (Donna Murphy), a psychiatrist, for advice. Alice Adams (Kellie Shanygne Williams) is Joan's friend and student teacher.
Shot entirely on location in Chicago, the series focuses on the private lives of an intimate group of friends and explores the complexity and endurance of close friendships among women, as well as the challenging relationship between Joan and Jake -- two bright, independent, experienced people -- as they blunder toward intimacy.