Certainly reminds me of MGM.s prior "Meet Me in St. Louis" in general structure, although I like this better, primarily because of the presence of 12y.o. scene stealer Billy Gray, in his first significant Hollywood film. The official leads: Doris Day and Gordon McRae, were 2 of the top film singers of the time. Although a number of songs are rendered, including the title song, music isn't the primary forte of this film. Rather, comedy and nostalgia are. Leon Ames reprises his role of father of the family, established in "Meet Me in St. Louis", while the quintessential small town mother of films: Rosemary Decamp is the mother of the Winfield family. Billy Gray is a treasure as the bratty little brother of (supposedly)18y.o. Doris. Gordon is the new boy next door(the Winfields having recently moved in), who immediately strikes up a troubled romantic relationship with Doris. They are on again , off again, beaus throughout the film, and through the sequel film: "By the Light of the Silvery Moon". Poor Jack Smith, as Hubert Wakely, is Doris's steady wannabe boyfriend, favored by father Ames, but not by Doris. She tries to tolerate him, after all he is a good piano player and decent singer. However, she being a tomboy, he bores her with his nerdy, high class, persona. Nonetheless, he never gives up hope. ......Doris begins the film as a baseball fanatic, wearing pants and a baseball cap around. But, after she meets Gordon, she changes into a gorgeous pink dress for an outing, and dons makeup. We see a similar transformation from an ultratomboy to a dress-wearing belle in the later "Calamity Jane", except that this transformation occurs late in that film vs. early in this film.....Mary Wickes plays her usual role as the family maid and cook. She has the misfortune of having her tray of china, silver pots and goodies knocked out of her hands 4 times by a swinging kitchen door: twice by Gray and twice by Ames. .....Ellen Corby has the misfortune of being Gray's schoolteacher, he being the class dunce and sleeper.......Esther Dale plays the elderly Aunt Martha, who makes the sage observation that "No man believes in marriage until a woman traps him into it.", in defense of Gordon's statement that he doesn't believe in marriage. Rosemary later agrees. She also gives Gray several 12th birthday presents, including a Swiss army knife, and a big sling shot that used to belong to father Winfield. He eventually makes mischief with both, as Aunt Martha expected. I don't want to spoil any more details. Just, see it if you can. Presently, it comes in a DVD packet with it's sequel: "By the Light of the Silvery Moon", which most people think is just as good. All of the principle players are retained in this sequel, except for John Smith, whose character is renamed as Chester, and played by Russell Arms. Doris and Gordon went on to make several other films together, as well, including "Tea for Two".