Reading Group Guide

Questions for Discussion

  1. Toby Griffin is a character that readers have alternately compared to Holden Caulfield in Catcher in the Rye, Bridget Jones in Bridget Jones’ Diary, Carrie Bradshaw in Sex and the City, and the nameless narrator of Bright Lights, Big City. How is Toby similar to or different from these characters?
  2. It could be said that Toby is often delusional about achieving fame and success in New York. What are Toby’s delusions about succeeding as a screenwriter? Are they realistic ambitions for a young person to have, ambitions that can motivate him to greater heights, or do they threaten to destroy him?
  3. Some of the characters in The Trouble Boy don’t have proper names; they are referred to as Subway Boy, Goth Boy, Decorator Guy, Real World Guy, or Army Guy. Why does the narrator refer to some characters with proper names and others with nicknames? Is there a pattern there? What significance does the title of the novel have in light of these
  4. The Trouble Boy is not a “coming out novel,” and yet the third chapter portrays an important coming out episode in Toby’s life. What other types of coming out does Toby have to do throughout the course of the novel?
  5. The third chapter of the novel is told in the third person. Why do you think the author chose to tell this part of Toby’s backstory in this way?
  6. What are Toby’s issues with intimacy? How does the third chapter of the novel reinforce these issues for him?
  7. Some of the sexual encounters in the book are portrayed in a way that is very graphic, and others, especially towards the end of the novel, are merely hinted at. Why do you think the author decided to portray the sex life of a twenty-two year-old like this? Is there a pattern to the portrayal of sexual encounters in the book? How do Toby’s issues with antidepressants and his libido play into this?
  8. One of Toby’s character traits is that he doesn’t realize that he often treats others as poorly as people treat him. Is his behavior justified? Is it a harsh fact of gay urban life (or even urban life in general) that there will always be some sort of “pecking order”?
  9. In The Great Gatsby, F. Scott Fitzgerald writes of Tom and Daisy Buchanan that they were “careless people…they smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made…” How does this quotation apply to some of the characters in The Trouble Boy, specifically Ariana, Jordan, and Cameron? Can it be applied to Toby as well? Besides the physical car crash, what other types of crashes take place in the novel?
  10. How do the car crash and potential for criminal prosecution function in the novel? If they had not occurred, would Toby have found redemption in some other way? How do you think his habits will change as he goes on with his life? What would you have done if you were placed in the same situation?
  11. Toby clearly has issues with drugs and alcohol, and yet the author never forces him to make any hard decisions about his substance use and abuse. Does Toby “hit bottom” in other ways? Did you want Toby to address his issues with substances directly, or did you feel it was implied that he would clean up his act?
  12. One of the great fears Toby has during the novel is that of contracting HIV. How does his fear manifest throughout the novel? Why is it that when confronted with his friend Jamie’s dilemma, his reaction is first compassion, then prejudice? Is Toby’s judgment of those with HIV insensitive, or is it simply a defense mechanism against something that he fears?
  13. The novel interweaves a number of social issues through the plot: alcohol and drug abuse, male eating disorders, safer sex, pregnancy, and HIV/AIDS. In many instances, Toby judges his friends for making choices to which he himself is not immune. Is it unfair of Toby to judge his friends? Is he judging them as a substitute for judging himself?
  14. Toby often says and does things that aren’t nice or compassionate. While he is not always a nice character, is he sympathetic? What are the ways in which you can or can’t sympathize with Toby?
  15. While Toby ultimately finds love with Andrew, one of the most intimate relationships in the book is the friendship between Toby and Jamie. How is this portrayed in the last scene between Toby and Jamie? Is it possible that while Andrew becomes Toby’s boyfriend, the real love affair of the book is between Toby and Jamie?
  16. In the final scene in the novel, Toby has tea with his mother, and tells her about what has been happening in his life. How does this scene conclude the novel? What are the ways in which Toby wants to please his parents, or gain their love and acceptance?
  17. What does the “trouble” in the novel’s title refer to? Is the trouble internal or external?
  18. The Trouble Boy is a novel in which many of the characters are gay, and yet it deals with issues that pertain to many readers, gay and straight, male and female. Would you classify the book as “gay literature”? How important are such classifications to you before you read a novel?