In "Searching for Caleb," a quirky, upper-class family is brought to life, with a focus on the Peck family's black sheep, Duncan. Duncan, who rejects the family's traditions and expectations, embarks on a quest to find his missing uncle Caleb, who disappeared decades ago without a trace. Alongside him is his cousin, Justine, who also feels out of place within their family. The novel explores themes of identity, family bonds, and the need for personal freedom.

The novel explores the complexities of family dynamics and personal growth through the eyes of a young man who returns to his coastal hometown in North Carolina from college in New York upon hearing of his sister's sudden marriage. As he reacquaints himself with his family's quirks and the rhythms of small-town life, he grapples with his own uncertainties about the future, his place in the family, and his understanding of home. The narrative delves into themes of nostalgia, the passage of time, and the bittersweet nature of coming-of-age, as the protagonist confronts the universal challenge of figuring out where he belongs in the world.

The novel unfolds as a faux memoir, structured around a grandson's conversations with his dying grandfather, revealing a tapestry of secret histories and hidden truths. The narrative spans the grandfather's adventurous life, from his involvement in hunting Nazis during World War II to his personal and emotional battles on the home front. The story delves into themes of love, loss, and the impact of secrets through the lens of a family's complex dynamics, set against the backdrop of mid-20th-century America, blending historical events with the fantastical elements of space exploration and model rocketry.

The book is a humorous and poignant examination of middle-aged masculinity, ritual, and nostalgia, centered around a group of men who annually reenact one of the most infamous plays in American football history, the 1985 Joe Theismann leg injury. Over the course of a weekend, these men gather to perform the ritual and in the process, delve into their personal lives, revealing their insecurities, failures, and struggles. Through the meticulous reenactment and the interactions among the characters, the novel explores themes of aging, friendship, and the longing for significance in the face of inevitable decline.