It is the only novel to feature Aubrey Upjohn, former headmaster of Malvern House Preparatory School, in person as a major character.

Aunt Dahlia's husband, Bertie's Uncle Tom, is trying to make a business deal with an American named Homer Cream.

The mischievous Roberta "Bobbie" Wickham, and Aubrey Upjohn, who was once Bertie and Kipper's oppressive headmaster, will also be there, along with Phyllis Mills.

Since Brinkley Court's butler, Seppings, is away on holiday, Aunt Dahlia engages the renowned psychiatrist Sir Roderick Glossop to step in as his replacement, adopting the alias “Swordfish”, so that he may observe and report on Wilbert's behaviour.

Bobbie ends her engagement to Kipper after reading an angry letter he wrote when he first saw the marriage announcement, and proclaims she will marry Bertie.

Bertie does not want to marry her, but is prevented by his personal code from turning down any woman, so he drives to Herne Bay to get help from Jeeves.

This initially upsets Aunt Dahlia, though it turns out that Wilbert is not actually the infamous Broadway Willie: that is his younger brother, Wilfred.

After receiving the typescript from Jeeves, Bobbie makes Upjohn withdraw his libel suit before she returns it to him.

Bertie, remembering receiving gifts from Uncle Tom while at prep school, replies, "How right you are, Jeeves!

For example, Bertie and Jeeves allude to Shakespeare's Macbeth and Hamlet in chapter 11: "[Poppet's] belligerent attitude is simple—""Sound and fury signifying nothing, sir?

"[4]In addition to picking up literary allusions from Jeeves, Bertie learns many words and phrases from him, especially Latin terminology.

For example, a ludicrous effect is created when Bertie combines the Latin phrase nolle prosequi, which he learned from Jeeves, with a Biblical reference when explaining to Bobbie that it was Balaam's ass that was noted for stubbornness, not Jonah's, in chapter 19: "Jeeves.""Sir?

[8] The expression "in the offing", used in the novel's title for the UK edition, describes something that is likely to happen or arrive soon.

The earliest extant notes for the novel, written by Wodehouse in November 1956, show that he initially planned for the plot to have Aunt Dahlia and Uncle Tom away in America, while Aunt Agatha and Lord Worplesdon were staying at Brinkley Court.

These characters include Uncle Tom's sister, Judson Coker (a character from Wodehouse's 1924 novel Bill the Conqueror), and Edwin the Boy Scout (the troublesome young brother of Florence Craye), who would have acted as a detective.

[11] A surviving late draft for the novel shows some small changes made by Wodehouse to make Bertie's language more comical and elaborate.

For example, in the sentence, "His blood pressure was high [, his eye rolled in what they call a fine frenzy,] and he was death-where-is-thy-sting-ing like nobody's business", the clause in brackets was inserted.

In the novel, Bertie describes the suspected playboy Wilbert Cream as resembling David Niven.

[15] However, Wodehouse biographer Richard Usborne complained that as a later novel, Jeeves in the Offing was not the author's best: "The plots creak a bit.