The novel explores the life of Cleo Judson, a Southern-born African American woman living in early 20th century Boston, who navigates the complexities of race, class, and society as she strives to create a facade of affluence and respectability. Married to a successful businessman, Cleo manipulates those around her to reunite with her estranged sisters and recreate the familial bonds and social standing she longs for. However, her scheming and pursuit of superficial success reveal the deep-seated insecurities and the cost of her ambitions, as she grapples with the true meaning of family and identity amidst the backdrop of the African American upper class.

The novel is a reflective account of the life of Harry Pulham, a middle-aged, conventional Bostonian who is prompted to examine his past and the choices he has made during the process of writing a Harvard class reunion biography. As he delves into his memories, he confronts his youthful ambitions, his experiences in World War I, and his complex relationships, particularly with a vivacious woman who challenged the conservative values of his upbringing. Through this introspection, Harry grapples with the realization that he has conformed to societal expectations at the expense of his own happiness, leading to a poignant exploration of the conflict between individual desires and societal pressures in early 20th-century America.

"The Late George Apley" is a satirical novel that presents a critical view of the upper class society in Boston during the early 20th century. The narrative unfolds through a series of letters, diary entries, and other documents, chronicling the life of George Apley, a wealthy Bostonian. The book explores Apley's struggles to uphold the traditions and social norms of his class, despite the rapidly changing world around him. The story provides a nuanced portrayal of the protagonist's life, highlighting the constraints and pressures of conforming to societal expectations.