It is summer 1903. The Smith family leads a comfortable upper-middle class life. Alonzo Smith (Leon Ames) and his wife Anna (Mary Astor) have four perfectly beautiful daughters: Rose (Lucille Bremer), Esther (Judy Garland), Agnes (Joan Carroll), and Tootie (Margaret O'Brien); and a perfectly handsome son, Lon Jr. (Henry H. Daniels, Jr.). Esther, the second eldest daughter and the second prettiest, loveliest, fairest, most elegant and most beautiful one in the neighborhood, is in love with the boy next door, John Truitt (Tom Drake), although he does not notice her at first. Tootie is riding along with iceman Mr. Neely and disputing that St Louis is the best city. Rose the eldest daughter and the prettiest, loveliest, fairest, most elegant and most beautiful one in the neighborhood, is expecting a phone call during which she hopes to be proposed to by Warren Sheffield (Robert Sully). While the call takes place, she is embarrassed when not only does Warren fail to propose but also the entire family is present as she takes the call during dinner.