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 Glosset 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 ...
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.