Taking place in Prohibition-era New York, The Small Bachelor tells the story of George Finch, a young man who has pursued his dream of becoming an artist in the big city, despite his lack of talent. Living a comfortable life after receiving a substantial inheritance two years ago, George spends his time sometimes painting pictures of dubious artistic quality, sometimes seeking the advice of his friend, the multitalented author J. Hamilton Beamish, and more recently finding the courage to propose to Molly Waddington, his dream girl.

George’s noble quest for love proves to be a difficult challenge, as he soon discovers after meeting Molly’s father and finding himself suddenly invited to dinner at the Waddington household. George has to face an increasing number of obstacles in order to win Molly’s heart and prove his worth as a husband, starting with having to earn the approval of Mrs. Waddington—who has already contemplated marrying Molly to a lord, and has no intention of allowing Molly to marry a man who can barely earn a living pretending to be an artist.

The reader is also given a glimpse into the lives of the unlikely group that surrounds George and Molly’s tale of romance, like a policeman with an affinity for poetry, a self-help scholar who becomes fascinated with a fortune teller, a reformed convict who has his eyes on a lady pickpocket, and more.

Published in 1927, The Small Bachelor is a great example of Wodehouse’s ability to craft comic fiction, mixing together converging storylines that focus on romantic trouble with fun and wacky hijinks, a rich vocabulary, and controlled narrative mayhem. The novel’s story and characters were inspired by a book written for the 1918 musical Oh, Lady! Lady!! by Wodehouse and Guy Bolton. The story would later be adapted into a 1927 silent movie of the same name and in the 2003 stage production Over the Moon.