Silent as a painting, the movie shows us day-dreamer Hermie and his friends Oscy and Benjie spending the summer of '42 on an US island with their parents - rather unaffected by WWII. While Oscy's main worries are the when and how of getting laid, Hermie honestly falls in love with the older Dorothy, who's married to an army pilot. When her husband returns to the front, Hermie shyly approaches her.

It's 1914 in New York City. Adult brother and sister Trippy Trellis and Fanny Trellis, whose parents are now deceased, were once wealthy, but Trippy squandered away the family fortune, about which no one knows except their cousin George Trellis and their many creditors. Fanny and Trippy still put on the façade to the outside world that they have money. The beautiful Fanny can have any man that she wants to marry, but she sets her sights on Job Skeffington, the son of Russian-Jewish immigrants. Job's wealth was self-made in finance. They met as Trippy was once employed by Job in his brokerage house. Fanny and Job, who is now aware of the Trellis' financial straits, ultimately do get married, much to the consternation of Fanny's many suitors, but most specifically to Trippy, who knows the reason why Fanny married him. Job also realizes that Fanny does not love him...