Bertram Wilberforce "Bertie" Wooster returns home with a hangover when a valet named Jeeves rings the doorbell. He fixes Bertie his special hangover cure, and when it proves effective Jeeves is immediately engaged. Bertie has lunch with his aunt Agatha - "the nephew crusher" - at which she announces he must marry, and that the suitable candidate is Honoria Glossop. Bertie has no intention of marrying anyone, and discovers that Bingo Little is in love with Honoria. He hatches a brilliant plan to get Honoria out of his hands and in to Bingo's...
Bertie's current love interest sets him up by giving both him and his rival Barmy the same idea for a practical joke, then gives away the terrier belonging to his Aunt Agatha which he is dog-sitting. Then Bertie is told to break up his friend Tuppy's interest in an opera singer.
When Bertie is instructed by Aunt Agatha to break up his uncle's engagement to a young waitress, he arranges a luncheon for his uncle and the girl's aunt, a common, gaudy woman -- who turns out to be the uncle's long-lost barmaid love. To escape Aunt Agatha's wrath, Bertie and Jeeves travel to the country residence of a friend to enjoy the local fair, where the bookie manages to handicap all the entrants on which Bertie and his friends bet.
Bertie tries to play Cupid without Jeeves' help. His friend Gussie is in love with Madeline, who happens to be staying at Bertie's Aunt Dahlia's house, so Bertie arranges for him to visit. Meanwhile, Aunt Dahlia is desperate to coax 500 pounds out of her husband for her failing magazine, and Tuppy's engagement to Angela Travers is off. Bertie's recommendation to both of them is the same: don't eat the wonderful food of Aunt Dahlia's chef Anatole at dinner, to show how lovelorn and miserable they are. But they become much more miserable when Anatole gives notice.
Bertie is offended because Jeeves was dispatched to convince Anatole to return to Brinkley Court, so he continues to attempt to reunite Tuppy and Angela and bring Gussie and Madeline together; consequently, Gussie and Angela wind up engaged, and Madeline expects Bertie himself to marry her.
Romantic entanglements are complicated by a unique silver cow creamer that is desired by both Bertie's Uncle Thomas and his rival, Judge Sir Watkyn Bassett. Sir Watkyn purchases the creamer by telling the shopkeeper, falsely, that Thomas had sent him. Bertie's Aunt Dahlia and friend "Stiffy" Byng both want him to steal the creamer for different reasons, but Judge Sir Watkyn has already sentenced him once (for stealing a bobby's helmet) and he doesn't want to go to jail.
Gussie writes down quirks of Sir Watkyn and Spode in a little notebook to give him confidence, but he loses the notebook. Stephanie finds it but declines to give it back until Jeeves convinces Sir Watkyn to allow her to marry Harold. When Jeeves' efforts backfire, Stephanie gives the notebook to Spode herself. Harold steals a policeman's helmet for Stephanie, who hides it in Bertie's room and then tells the constable and her father that Bertie stole it.
First, Bertie is summoned to a seaside resort by Aunt Agatha, who has a suitable marriage candidate for him. It's just a coincidence that the pearls the young lady pledges as collateral for a loan look exactly like the ones missing from Aunt Agatha's room ... or is it? Then, another of Bertie's friends winds up engaged to Honoria Glossop after misplacing the young lady he wanted to marry, and Jeeves is surprisingly unwilling to assist the friend in regaining his freedom.
Jeeves gives notice when Bertie plans to continue his less-than-inspired horn playing during a country vacation. Chuffy rents Bertie a country cottage and hires Jeeves as his new gentleman's gentleman. Chuffy is in love with an American heiress and distressed when he discovers she was once engaged to Bertie. A massive blowup leaves Chuffy and family not speaking to the Americans.
Barmy has put together a group of alleged musicians to play in blackface at his aunt's 50th anniversary party. Pauline, in London, is alarmed because a man is following her, so Bertie is drafted to escort her to Chuffnell Hall in her car. Naturally, they run out of gas and have to spend the night at a little pub. Chuffy is understanding when Stoker blabs about the two of them spending the night on the road, which offends Pauline; doesn't he care enough to be jealous of her? Stoker lures Bertie onto his yacht and locks him in a stateroom until a forced marriage can take place; Jeeves liberates Bertie, who escapes by posing as one of the blackface musicians. Bertie, Stoker, Sir Roderick, and all Barmy's musicians wind up arrested in blackface in front of Chuffy as the local magistrate.
Bertie decides he would like a child to brighten up his mundane life and considers adoption. After being mistaken for a burglar, he is coerced into giving a speech at a girls' school, which sours his view of children and knocks the idea on the head. Tuppy suffers broken bones whilst playing in a brutal village rugby match to impress new flame Daisy and Bingo subjects his uncle to endless readings from romantic novels to sweeten him up when Bingo starts dating a waitress. Such extreme behaviour convinces Bertie that he is better off single.
Fleeing from the twin horrors of prospective marriage and the baleful Aunt Agatha, Bertie sails to New York with Jeeves, where he hopes to lie low but instead he is charged with minding the ultra-shy mother's boy Wilmot, son of Lady Malvern, and showing him the high life. Oddly enough Wilmot takes only too well to the night-spots of Manhattan, wearing Bertie out in the process. Tuppy Glossop also arrives, to talk about car exportation with wealthy businessman Mr. Stoker. Unfortunately Tupper's business plan is nowhere near as lofty as it should be.
Bertie is faced with problems. One is how to allow the indolent 'Bicky' Bickersteth to remain in Manhattan and still receive an allowance from his luxury-hating father, the Duke of Chiswick. The other involves reclusive poet Rocky, who lives an austere life in a cabin in the country, which inspires his verse. His aunt Isabel wants him to move to the big city and send her his impressions of the night-life there, which is anathema to him. There is a solution, of course, which involves a little mutual aid, but until Jeeves sorts it out, it's Bertie who finds himself living in neither one place nor the other.
The latest misfit whom Aunt Agatha has short-sightedly ordered Bertie to take under his wing is Cyril Bassington-Bassington, a young aristocrat whose mother has sent him across the Atlantic to cure him of his obsession with the theatre.It is the worse thing she could have done. Cyril goes to a Broadway show, gets involved with a chorus girl and becomes a star of the musical theatre himself touring across the States. Bertie also has to help portrait painter Corky with his love problems.
Bossy Aunt Agatha orders Bertie to go to Deverill Hall and woo Gertrude Winkworth. Gussie Fink-Nottle is due to go to the hall to impress Dame Daphne, Gertrude's mother and godmother to his beloved Madeleine Bassett. When Gussie is arrested for trying to catch newts in Trafalgar Square fountain, Bertie sees the chance to obey Agatha by going to the hall and also save the day for Gussie by impersonating him. When Gussie eventually turns up he has to pretend to be Bertie. Gertrude is captivated by him, romance blooms and Gussie writes to Madeleine to end their relationship. Bertie's efforts to retrieve the letter leads to his arrest and, worse, the attentions of Madeleine before Jeeves rescues him yet again.
Jeeves does not approve of Bertie's new betrothed, bossy Lady Florence Craye - author of 'Strength Through Willpower', particularly when, during a weekend party at Totleigh Court, she orders Bertie to steal and destroy Sir Watkyn Bassett's memoirs,whose publication could cause large scale embarrassment. Wooster steals the manuscript and gives it to Jeeves, who, as always, knows best. Suffice to say, the engagement is soon over. Jeeves is more sympathetic to Gussie Fink-Nottle, when Stiffy Byng, by whom he is captivated, persuades him to retrieve her dog,who has bitten and been confiscated by P.C. Oates during rehearsals for the annual village variety show.
Wearing a false beard, Bingo Little pretends to be a friend of the workers to impress Charlotte Corday Rowbotham, daughter of a socialist orator, to the disgust of her other admirer Comrade Butt. Fortunately Jeeves is on hand to scupper Bingo's romance, leading to a free-for-all at the races but Bertie has a bigger problem. In order to get in with novelist Cornelia Fothergill whose stories she wants to publish in her magazine, Aunt Dahlia charges Bertie to steal a hated painting by Mrs. Fothergill's father-in-law which has long blighted her marriage. Bertie is, of course, a hopeless thief, and, somewhat surprisingly, the fearsome Spode comes to his rescue - along with Jeeves of course.
Bertie is back in New York and enamoured of portrait painter Gwladys Pendlebury but Aunt Agatha is not enamoured of the painting of her Bertie commissioned and she is even more annoyed when her wayward twin sons, charged to Bertie's care before being shipped off for colonial posts, give him the slip to pursue a cabaret singer. Tuppy Glossop arrives to sell his family recipe for cock-a-leekie to soup magnate Slingsby to finance his nuptials to Elizabeth but slimy ad man Lucius Pim steals Gwladys from Bertie and makes Aunt Agatha the unwitting face of Slingsby's soups on every billboard in New York.
In a New York Bookshop where he is buying Jeeves a birthday present Bertie meets forceful old flame Lady Florence Craye who has rowed with fiance 'Stilton' Cheesewright and decides she wants to get engaged to Bertie again. 'Stilton' decides he wants to do Bertie a mischief. Florence's father Lord Worplesdon, Aunt Agatha's second husband, is in New York to sell his boats to businessman J. Chichester Clam but the deal is meant to be secret and the press keep pursuing Clam - even on the hotel fire escape. His Lordship's niece Nobby will benefit by the deal as it will gain her the money needed for her beau George Caffyn to put on his play. Jeeves decides that to preserve anonymity everyone should meet in disguise at a penthouse fancy dress party, leading to confusion in high places.
Unwelcome familiar faces turn up to destroy Bertie's New York idyll, starting with Bingo Little, who wants to marry the English waitress at Art's Diner and persuades Bertie to impersonate romantic novelist Rosie M. Banks again to make his uncle, Lord Bittlesham, favour the union. Old flame Honoria Glossop and her doctor father Sir Roderick are also in town, the latter wanting to wed his nurse but needing to marry off Honoria first. Bertie's plan to goad her shy suitor Blair into proposing by making him jealous goes horribly awry, as does his hiring of a gold-digging actress, Trixie, to pose as his betrothed, to get Honoria off his back. When Bingo marries the waitress, who turns out to be the real Rosie M. Banks, Bertie is exposed as a fraud and everyone is after him. Even on the liner home. The only solution is for him and Jeeves to jump ship - literally.
Aunt Dahlia aims to sell her ailing magazine to Scouse parvenu Mr. Trotter but hocks her pearls to afford to pay a famous female novelist to contribute a story to the magazine, to reel in Trotter. Bertie, having been arrested in The Mottled Oyster speakeasy, where he has accompanied Lady Florence Craye to research her new book, is charged to 'steal' the fake pearls which Dahlia has substituted before her husband finds out - which involves his dressing as a thieving housemaid. Jeeves too dons drag to impersonate the great lady novelist, in the process attracting the unwanted attentions of Florence's oafish beau 'Stilton' Cheesewright, though at least it gets him off Bertie's case.
The latest house party at Totleigh Towers sees 'Stiffy' Bing trying to strong-arm Bertie into stealing an African tribal statue which, she believes, has put a curse on the Bassetts. Bertie's midnight exploits bring him into contact with Gussie Fink-Nottle who, rebelling against his betrothed Madeleine Bassett's efforts to turn him into a vegetarian, is enjoying meaty midnight feasts with Emerald, the comely American cook. Bertie steals the statue but when Major Plank, from whom it was bought, refuses to have it back, he ends up blacking up and impersonating an African tribal chief anxious to restore the statue to his tribe, Unfortunately real Africans arrive and once more it's Jeeves to the rescue.
Overjoyed that Madeleine Bassett is to marry Spode and stop pursuing him Bertie goes to Totleigh Towers for the wedding, meeting another Drone, drippy Ginger Winship, whose bullying fiancee ,Lady Florence Craye, is forcing him to stand for Parliament, or she will leave him. Sneaky ex-valet Brinkley has stolen the book from Jeeves' club in which manservants dish the dirt on their employers and hopes to make money by selling it to Ginger's Labour party rival but Bertie steals it, unaware that Ginger wants to be discredited so he will lose the election and Florence and can marry his secretary Magnolia whom he really loves. An outraged Florence declares that she is re-engaged to Bertie and Madeleine argues with Spode, also announcing her intention to wed Wooster. Fortunately the book contains information on Spode, which Bertie uses to make him marry Madeleine, whilst Florence takes a shine to Brinkley. Unfortunately the Totleigh Towers plumbing, which is plainly on its last legs and not helped by being serviced by Tuppy Glossop's new drain-cleaning machine, decides to erupt in the middle of the wedding, spraying the congregation with effluent. Jeeves and Wooster make a very swift exit.