What qualities does Cherry admire in both Bob and Dally in The Outsiders?

In The Outsiders, Cherry's admiration of Bob and Dally is surprising given her distaste for violence and crime. Both Bob and Dally are violent and frequently engage in criminal behavior. However, they are also both strong, charismatic, and able to make people listen to them. Cherry recognizes these qualities in Bob and Dally. She is self-aware and realizes that she is attracted to men who are strong but also violent. She sees that these men are not good for her.

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Both Dally and Bob are violent characters, which makes Cherry's admiration of them ironic given her strong distaste for violence and criminal behavior. Not long after arguing with Dally and throwing her drink in his face, Cherry tells Ponyboy, "I could fall in love with Dallas Winston . I...

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Both Dally and Bob are violent characters, which makes Cherry's admiration of them ironic given her strong distaste for violence and criminal behavior. Not long after arguing with Dally and throwing her drink in his face, Cherry tells Ponyboy, "I could fall in love with Dallas Winston. I hope I never see him again, or I will." Ponyboy is shocked and confused by Cherry's statement and does not understand what she sees in Dally:

I studied Dally, trying to figure out what there was about this tough-looking hood that a girl like Cherry Valance could love. Towheaded and shifty-eyed, Dally was anything but handsome. Yet in his hard face there was character, pride, and a savage defiance of the world.

After Bob attacks Johnny and Ponyboy, Cherry defends him:

Oh, maybe Bob asked for it. I know he did ... You only knew his bad side. He could be sweet sometimes, and friendly ... I know I'm too young to be in love and all that, but Bob was something special. He wasn't just any boy. He had something that made people follow him, something that marked him different, maybe a little better, than the crowd.

Ponyboy reflects on Cherry's feelings about Dally and Bob:

Cherry saw the same things in Dallas. That was why she was afraid to see him, afraid of loving him ... Cherry went for boys who were bound for trouble.

Cherry is extremely self-aware. She knows what her weaknesses are and tries to avoid them. She admits to being attracted to Dally but also says she hopes to never see him again because she does not want to fall in love with him. She acknowledges that he would not be good for her. She dates Bob despite his violent nature because she is attracted to his charisma and leadership skills. She recognizes these same qualities in Dally. Her opposition to violent behavior is partially due to her awareness of her attraction to violent men.

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That's an interesting question, because it is plainly made clear to readers that Cherry likes whatever Dally has got going on a whole lot.

She looked at me quickly. "I could fall in love with Dallas Winston," she said. "I hope I never see him again, or I will."

That's an amazing statement from a girl that is fairly committed to nonviolence and hates criminal behavior. In fact, she even detests it when her boyfriend drinks alcohol, yet she admits that she is deeply attracted to a guy like Dally. Dally is a legitimate criminal. He's such a "bad boy" criminal, that Ponyboy lets readers know early on in the book that he doesn't like Dally.

[...] he got drunk, he rode in rodeos, lied, cheated, stole, rolled drunks, jumped small kids—he did everything. I didn't like him, but I had to respect him.

Readers might argue that Pony's opinion of Dally changes throughout the story, but I don't think so. I think Ponyboy respects Dally and trusts him, but I don't think Ponyboy would ever desire to be close friends with Dally. On the other hand, Cherry knows that she is so attracted to him that she needs to stay away from him. Bob is essentially the same person as Dally except on the Soc side of the equation, and that is probably why Cherry is his girlfriend. If you could ask Cherry what it is about those boys that she likes so much, she couldn't tell you. She tries to explain it, but everything she says is so vague.

"I know I'm too young to be in love and all that, but Bob was something special. He wasn't just any boy. He had something that made people follow him, something that marked him different, maybe a little better, than the crowd. Do you know what I mean?"

Cherry is exceptionally good at reading people. That was made clear to readers early in the book when she figured out that something bad had happened to Johnny. She simply knew. That is what she tries to explain. She knows that there is a quality about guys like Dally and Bob that instantly causes other people to gravitate toward them and respect their actions, words, and person. She sees in those boys the capability of strong, male leadership, and I think that is what she is ultimately attracted to.

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Despite the fact that Bob Sheldon and Dally Winston have violent, reckless qualities, Cherry admires both boys for their natural charisma, spontaneity, rebellious personalities, and leadership skills. Ponyboy is shocked when Cherry first comments that she would fall in love with Dally. As the story progresses, Pony develops a different perspective on Dally and understands that Cherry admires his independent, rebellious personality. She has the ability to see through Dally's tough exterior and admires his courage and selflessness. Despite his many negative character traits, Dally is an honest, helpful friend who lives by his own rules and is respected by his peers. Cherry also admires Bob Sheldon's charisma and independent personality. Cherry tells Ponyboy in chapter 8,

He [Bob] wasn't just any boy. He had something that made people follow him, something that marked him different, maybe a little better, than the crowd (Hinton 110).

After Cherry makes this remark, Ponyboy comments that she also sees the same qualities in Dally, which is why she is attracted to him.

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