According to Randy, Bob's best friend and confidante, all Bob really just wanted:
"to make someone say 'No' and they never did. They never did. That was what he wanted [...] To have somebody lay down the law, set the limits, give him something solid to stand on" (116).
Bob's frustration came from having parents that spoiled him too much. The reader can easily deduce that Bob's wild behavior resulted from his parents' negligently permissive attitudes. He tested their limits to see if they cared enough to make him stop. Randy even references a time when Bob came home extremely drunk to see if his parents would punish him, but they responded by taking the blame for his actions and poor decision making. Randy speculates that perhaps if Bob's parents would have had a firmer hand in his upbringing then his friend might "might still be alive" (116).