Harold Horne, an apprentice clerk in a Honolulu shoe store, is ambitious and hopes to rise in John Tanner’s organization, but his nervousness at waiting on Mary, a lady customer, causes numerous distractions, including the loss of her dog in the street, resulting in amusing complications with taxi drivers. As social secretary to wealthy Mrs. Tanner, Mary declares her confidence in the enterprising Harold, while he confides to Mr. Carson, a roomer in his boardinghouse, that he will take a correspondence course to become rich and worthy of Mary. Harold crashes a series of society gatherings and boasts of his prowess at polo and other pastimes of the wealthy, but later he makes a general botch of Mrs. Tanner’s shoes and stockings at the store, trying to elude Mary’s glance. In delivering shoes to an ocean liner, Harold is forced to remain aboard; he discovers Mary is only a secretary. To escape being caught, Harold hides in a mail bag and in a series of maneuvers ends up flying to San Francisco, where he delivers an urgent bid for Tanner, saving Mary her job, and winning himself a promotion as well as a wife. More on Wikipedia
Watch Feet First (1930)