Jacob Booth is watching a murder trial. He notices a beautiful girl. She is Jenny Delehanty, sister of the accused murderess Mrs. Choyinski. Jenny’s beauty is at odds with her rough speech, but Booth feels sorry for her as reporters badger her. Booth takes pity on her and escorts her from the courtroom. He graciously offers to introduce her to a movie director.
Booth arranges for her to meet Billy Farelly, a movie director. She chooses the stage-name Tootsie Defoe, but Booth encourages her to make the more sophisticated change to Jenny Prince. He buys her a dress to celebrate being signed up for three lead roles. She is sixteen, and grateful to him, but he is unwilling to take advantage of her. He warns her against alcohol and is "chilled by the innocence of her kiss."
A month later, Booth is warning Farelly not to seduce Jenny. He says he is not in love with her, but realizes that she is very important to him. On her side, Jenny says Booth is her only friend. Inspired by Jenny's career success, Booth tries to see if his vocal chords can be fixed so that he may resume his singing career, but the doctor finds no cause for hope.
When he sees Jenny again she is seventeen, and has grown up quickly. He wants to spend time alone with her, but they have three parties to go to. He is mildly jealous of Raffino, the attractive male lead who seeks Jenny’s attention at the party. He tells Jenny that he loves her, and she says that he does not.
Jenny agrees that she would marry him, but he doesn’t excite her. She says she is happy and comfortable with him. Booth comes to her rescue when a blackmail attempt is made in the name of her sister, with a man called Scharnhorst saying he would reveal her connections to the convicted murderess.
Jacob continues his life as Jenny becomes more famous. She writes to him, but he is glad when she is on location in Arizona. When he sees her again she is a fully developed, confident, beautiful woman. He renews his marriage request but she has fallen in love with a man on location. He hopes to change the course of events but knows it is futile: Jenny will go on without him. He sees her name over a movie theater and, just as he had gone as a spectator to the trial, he follows the crowd and goes in to watch the show.
The cyclical nature of the story is shown both at the beginning and the end. Jacob Booth is only ever a spectator in Jenny’s life: he never has a leading role.
Jenny’s grating, limited language clashes with her good looks, and her speech is vividly described as "toad words." We are told early in the story that Booth "valued things rather than cared about things," although at the end we may feel that he certainly wanted Jenny from the point she became a woman. He finds her ways innocent and crude: similarly, she is overwhelmed with his courtesy. Although Jacob certainly has a romantic and sexual interest in Jenny, he is realistic and aware of the age difference. Rather than being attracted by her innocence and vulnerability, it is a turn-off. Because he is fundamentally a pretty nice fellow, Jacob wants only to wait for Jenny to grow up enough for him to feel comfortable loving her.
Booth’s attempt to have his vocal chord problem re-examined indicates that he wishes to regain his lost talent. When told this is not possible, he lives vicariously through Jenny. She blossoms quickly – "at seventeen, months are years and Jacob perceived a change in her; in no sense was she a child any longer." He is keen to possess her, but Jenny correctly works out that he is not really in love with her.
She agrees to marry him out of loyalty and duty, which is not what either of them really wants. It would be a bargain as corrupt as Scharnhorst’s blackmail attempt.
When Jenny does fall in love, it is not with Jacob. The title's allusion is to Jacob’s ladder in the Old Testament - the ladder does not really lead to heaven for either Jacob. There are also allusions to Edgar Allen Poe’s narrative poem, The Raven in the sad repetition of "never any more," echoing the raven’s cry of "nevermore" that tortures the lover int he poem.