The Trouble Boy, page 29
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. Some of the sexual encounters in the book are portrayed in a way that is very graphic, and others, especially toward 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?
7. 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”?
8. 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?
9. 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?
10. 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?
11. 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?
12. 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?
13. 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?
14. 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?
15. 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?
TOM DOLBY was born in London and grew up in
San Francisco. His writing has appeared in The Village
Voice and Time Out New York, and he is the author
of the downtown guidebook CityTripping New York.
He is currently working on his second novel, which takes
place at a boarding school. For more information,
go to www.tomdolby.com.
This book is a work of fiction. Names, characters, places, and incidents either are products of the author’s imagination or are used fictitiously. Any resemblance of any of the fictional characters to actual persons, living or dead, is entirely coincidental.
KENSINGTON BOOKS are published by
Kensington Publishing Corp.
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Copyright © 2004 Tom Dolby
The author gratefully acknowledges the following publishers for permission to reprint the following lyrics:
“I’ll Be Your Mirror.” Words and music by Lou Reed. © 1966 (Renewed 1994) Oakfield Avenue Music Ltd. All rights controlled and administered by Screen Gems-EMI Music Inc. All rights reserved. International copyright secured. Used by permission.
“Downtown.” Words and music by Tony Hatch. Copyright © Wellbeck Music Ltd. Administered by Universal-MCA Music Publishing, a division of Universal Studios, Inc. (ASCAP) International copyright secured. All rights reserved.
All rights reserved. No part of this book may be reproduced in any form or by any means without the prior written consent of the publisher, excepting brief quotes used in reviews.
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ISBN: 978-0-7582-0617-6
Tom Dolby, The Trouble Boy



