City Boy

A Novel

City Boy

Newlyweds Jack and Chloe are building a life together in a modest Chicago apartment. The city is theirs to enjoy as Jack struggles to pursue a writing career and Chloe works downtown, applying herself to the world of high finance. While Jack aspires to be the perfect husband, his own self-doubts and Chloe's office flirtations cast shadows. Jealousy and mis-behavior undermine their notions of themselves and of each other, and their lives take on uncomfortable parallels with the volatile, chaotic existence of their raffish, menacing neighbors. In the intense heat of one Chicago summer, Jack and Chloe's marriage roils into a queasy chemistry of vanity, lust, and greed. Thompson writes with piercing insight and emotional truth, setting off literary fireworks.
  • Simon & Schuster | 
  • 320 pages | 
  • ISBN 9780743242837 | 
  • April 2005
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Reading Group Guide

Reading Group Guide for City Boy by Jean Thompson
1) What does the city of Chicago represent to Jack? Does Chloe share his opinion of the city? What images of the city does the author give the reader and what do these images represent?
2) Chloe and Jack share a complex relationship. Discuss the nature of their meeting and how those first experiences with each other shaped what their relationship eventually became. Was the progression a natural one? Was it expected?
3) How does Chloe change throughout the novel? What events in her marriage and career seem to influence her choices? How does the inclusion of her journal in the novel help tell her side of the story?
4) Describe the relationship between Ivory and Jack. What does Jack ultimately gain from becoming involved with Ivory? Why do you think Ivory becomes involved with Jack? Are there any similarities in their respective relationships with other people?
5) The characters in the novel make questionable decisions in their lives and relationships. Discuss the morally ambiguous situations Jack, Chloe and Ivory find themselves in and how they are resolved, if at all. How do their decisions ultimately affect each other?
6) "His sodden brain was busy contending with the surprise of Chloe saying what he himself felt, at least on occasion, that the kid and his ragtag household represented something one might envy." What does this passage indicate about Jack and Chloe? What do Rich Brezak and his wa see more

More Books from this Author

The Year We Left Home
Do Not Deny Me
Throw Like A Girl
Wide Blue Yonder

About the Author

Jean Thompson
Marion Ettlinger

Jean Thompson

Jean Thompson is the author of Who Do You Love: Stories, a 1999 National Book Award finalist for fiction, and the novels City Boy and Wide Blue Yonder, a New York Times Notable Book and Chicago Tribune Best Fiction selection. She lives in Urbana, Illinois. Visit her at