A daughter and her friend try to find a husband for a widow planning to marry a banker to provide for them.
At school Buzz Mitchell (Freddie Bartholomew) forgets his speech about Daniel Webster, and Pinkie Wingate (Judy Garland) sings "Zing! Went the Strings of My Heart." Arthur Drubbs (Gene Lockhart) proposes to Dottie Wingate (Mary Astor), who says she will think it over. Pinkie hears her mother crying and offers to get a job; but Dottie says Pinkie's voice should be trained so she can be independent. Pinkie cries and tells Buzz that she fears Dottie will marry Drubbs. Uncle Joe (Charley Grapewin) gives Buzz an advance so they can take Dottie on a trip with their trailer. Buzz and Pinkie plead that Dottie not marry Drubbs for money. As they drive, Pinkie sings "On the Bumpy Road to Love." Dottie tells Buzz that she plans to marry Drubbs. Buzz tells Pinkie that Dottie wants that but suggests they find someone better.
While camping they meet Richard Thurlow (Walter Pidgeon). Buzz learns he is a bachelor lawyer and invites him to dinner; but Richard leaves. Buzz finds Richard, and little Billie Wingate (Scotty Beckett) causes a skunk to stink. Richard complains to Dottie, who laughs. Buzz and Pinkie urge Billie to bury his clothes. Wealthy neighbor J. J. Slattery (Alan Hale) hears the commotion and persuades Billie. Richard apologizes to Dottie, who invites him to dinner. Buzz learns that Slattery's wife died and tells him about Dottie. In the rain Richard with Dottie runs out of gas. At Slattery's house Pinkie sings to Billie "Ten Pins in the Sky." Richards thanks Dottie for a wonderful day but says he wants no responsibilities.
Pinkie tells Buzz that Dottie cried again. Buzz wants Dottie to marry Slattery; but Pinkie says that Richard would make her happy. Richard brings flowers to Dottie and invites her to Slattery's. Dottie says she is going home to marry a banker. Pinkie asks Slattery to take Billie and her so that Dottie can be free with Richard, but Slattery tells Pinkie that Dottie would not be happy without her children. Slattery tells Richard that Pinkie said that Dottie is running away from someone she loves. Police stop Buzz and the Wingates until Richard gets there to join them. Happily they drive off together.
Dottie and Richard grapple with the dilemma between the freedom of a carefree life versus the responsibilities for loved ones. The woman naturally puts her children first, and the man gives up his freedom for a woman he loves. This traditional story is enlivened by the plotting of the youngsters and three fine songs.