Harold Meadows (Lloyd) is a tailor's apprentice for his uncle in Little Bend, California. He is so shy around women that he can barely speak to them (to stop his stuttering, his uncle has to blow a whistle). Despite this, Harold writes a "how to" book for young men entitled "The Secret of Making Love", detailing how to woo different types of young women, such as "the vampire" and "the flapper" (in scenes that parodied two other popular films of the time, Trifling Women and Flaming Youth), and takes a train to see a publisher in Los Angeles.
The same day, rich young Mary Buckingham (Ralston) boards the same train after her automobile breaks down in Little Bend. No dogs are allowed aboard, so she hides her Pomeranian under her shawl, but her pet jumps off as the train pulls away. Harold rescues her dog and helps Mary hide it from the conductor. She sees his manuscript, so he starts telling her about his book, overcoming his stuttering in his enthusiasm. They become so absorbed in each other that neither realizes that the train has reached its final destination and everyone else has departed. Upon returning home, Mary rejects the latest in a string of marriage proposals from persistent suitor Ronald DeVore, a rich man almost twice her age.
After her car is repaired, Mary intentionally detours through Little Bend repeatedly, hoping to see Harold again. On one such trip, Ronald is also along for the ride, and his unwanted attentions cause Mary to swerve and get her car stuck near the outskirts of Little Bend. While Ronald walks back to town for a tow, Mary runs into Harold. After telling Mary about the remainder of his book, Harold informs her that he is going to see the publisher, Roger Thornby, in a few days to deliver a new chapter that will be about her. They agree to meet again afterward. Meanwhile, Ronald runs into a middle-aged woman who asks if he is finally going to introduce her to his family, but he stalls, then rides away in the tow-vehicle.
Mr. Thornby's professional readers find Harold's book hilariously absurd, so he rejects it. Without any royalty money, Harold figures he cannot ask Mary to marry him. So he pretends that he was only using her as part of his research. Heartbroken, Mary impulsively agrees to marry Ronald. Afterward, though, one of Mr. Thornby's senior employees convinces him that, if the staff liked the book so much, there must be a market for it, so Thornby decides to publish it as "The Boob's Diary".
A few days later, a depressed Harold gets a letter from the publisher, but just rips it up without opening it, assuming that it is a rejection notice. Fortunately, his uncle notices that one of the scraps is part of an advance royalty check for $3,000; the accompanying letter states that the book will be published as a comedy. At first, Harold is outraged, but then he realizes that he can propose to Mary after all. However, when he sees a newspaper headline announcing Mary and Ronald's wedding that same day at her family's estate, he gives up. By chance, the same woman whom Ronald had met a few days earlier walks in and, seeing the newspaper story, tearfully exclaims that she is Ronald's wife. As proof, she shows Harold a locket with the couple's wedding portrait and the engraved words "to my wife" that Ronald had given her two years earlier.
Harold embarks on a frenzied headlong dash, involving bootleggers, car chases and multiple changes of vehicle (from missing the train to various cars to a trolley to a police motorcycle to a horse-drawn wagon to horseback), through the countryside and along the crowded streets of Culver City and Los Angeles. He bursts in just in time, but he cannot stop stuttering long enough to expose Ronald's intended bigamy. So Harold simply carries Mary off. When they are alone, he tells her about Ronald's secret and shows her the locket. Mary gets Harold to propose (with an assist from a passing mail carrier's whistle), and she accepts.Harold Lloyd as Harold Meadows, The Poor Boy
Jobyna Ralston as Mary Buckingham, The Rich Girl
Richard Daniels as Jerry Meadows, The Poor Man
Carlton Griffin as Ronald DeVore, The Rich Man
Nola Dolberg as Vamp Girl (uncredited)
Judy King as Flapper Girl (uncredited)
(Unknown) as Publisher Roger Thornsby
William Orlamond as Thornsby's Assistant (uncredited)
Gus Leonard as Bearded Train Passenger (uncredited)
Earl Mohan as Sleeping Trolley Rider (uncredited)
Joe Cobb ("Our Gang") as Boy in Tailor Shop (uncredited)
Jackie Condon ("Our Gang") as Boy in Tailor Shop Having Pants Sewn (uncredited)
Mickey Daniels ("Our Gang") as Newsboy (uncredited)
This was Lloyd's first independent production after his split with Hal Roach. It is what Lloyd called a "character story" (as opposed to a "gag film"), and is notable for containing fewer of the stunts which characterize Lloyd's other films throughout most of its length, and instead focusing more on the relationship between Lloyd and Ralston. However, the lengthy finale of the film is one of the most exhilarating, non-stop action sequences of Lloyd's career.
It was also the second of six consecutive movies pairing Harold Lloyd and Jobyna Ralston, who left Hal Roach Studios as well to continue working with Lloyd. Unlike the normal style for filmed romances prior to Girl Shy, both Ralston and Lloyd were featured in comedic scenes.
The exterior shots of the "Buckingham" mansion and gardens were filmed at Lloyd's own Greenacres estate in Beverly Hills.