What was Bob's "real" problem, according to Randy, in The Outsiders?
In Chapter 7, Randy Adderson stops by the Tasty Freeze to have a conversation with Ponyboy before the rumble. When Ponyboy gets into his car, Randy tells him that he won't be at the rumble and is going to leave town. Randy begins to talk to Ponyboy about his friend Bob Sheldon, who lost his life the night he tried to drown Ponyboy. He tells Ponyboy that Bob's parents spoiled him rotten and let him get away with everything. According to Randy, Bob's problem was that his parents never set any boundaries for him or punished him for his misbehavior . Whenever Bob would get into trouble, his parents would blame themselves, and Bob would go unpunished. Randy says that Bob needed somebody to "lay down the law" and tell him "no." Randy believes that if Bob's father would have beaten him with a belt just once in his...
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life, Bob would probably still be alive.
Bob is Cherry Valance’s boyfriend. He is responsible for brutally attacking Johnny, which forces Johnny to carry a switchblade for protection. It is the same switchblade that ends up killing Bob after he almost drowns Ponyboy. In order to defend Pony, Johnny stabs Bob to death and the two friends are forced to escape to Jay Mountain. Pony later confirms from Cherry that it was indeed Bob that attacked Johnny, because the rings he wore on his fingers matched Johnny’s injuries.
On the other hand, Bob’s friend Randy is unable to stomach the senseless violence and decides to quit fighting. He bumps into Pony before the rumble and they have a chat in his car. Randy tells Ponyboy of challenges faced by the Socs and how Bob was just a normal kid going through the same challenges. Randy blames Bob’s upbringing for his behavior. He states that Bob was spoiled and his parents failed to provide the necessary guidance despite his attempts to seek their attention. His parents never confronted him when he did something wrong, forcing him to vent his frustration on society.
"He's dead--his mother has had a nervous breakdown. They spoiled him rotten. I mean, most parents would be proud of a kid like that--good-lookin' and smart and everything, but they gave in to him all the time. He kept trying to make someone say 'No' and they never did. They never did. That was what he wanted. For somebody to tell him 'No,' to have somebody lay down the law, set the limits, give him something solid to stand on. That's what we all want, really."