What draws Cherry to the greasers in The Outsiders?

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This is a great question! At first glance, it does seem odd that Cherry would empathize with and even help the Greasers when socially, they are the enemies of the Socs. In my opinion, the answer lies in Cherry's relationship with Ponyboy . She seems curious about the Greasers, but...

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This is a great question! At first glance, it does seem odd that Cherry would empathize with and even help the Greasers when socially, they are the enemies of the Socs. In my opinion, the answer lies in Cherry's relationship with Ponyboy. She seems curious about the Greasers, but probably never had interactions with one of them prior to meeting Ponyboy. Early on in the conversation, she has with Ponyboy at the drive-in movie theater she asks Ponyboy about his brother.

"Your brother Sodapop, does he work at a gasoline station? A DX I think?"

"Yeah."

"Man, your brother is one doll. I might have guessed you were brothers—you look alike."

Cherry is a romantic and sensitive girl. She finds herself attracted to Dallas Winston, even though she thinks he's crude and even calls him "dirty." She says, "I kind of admire him." I believe she means that she admires his attitude and his freedom. He is free from fulfilling the expectations of others, whereas she is a slave to social pressure. He is also very confident in himself, whereas Cherry is subject to a complicated social order that probably invites doubts about oneself.

Nothing is real with us. You know, sometimes I'll catch myself talking to a girl-friend and realize I don't mean half of what I'm saying. I don't really think a beer blast on the river bottom is super-cool, but I'll rave about one to a girl-friend just to be saying something.

Cherry says this to Ponyboy when she is analyzing the difference between their social groups with him. It's clear that this kind of social interaction is against her nature, and she finds in Ponyboy someone she can truly connect with on an emotional level, something she can't do with her own friends.

She finds in Ponyboy a human connection to the Greasers. Ponyboy is sensitive and romantic just like she is. As the novel progresses, she realizes the part her boyfriend played in the incident that caused his death. She wants to do the right thing, so she helps the greasers in several ways, while still being restrained by the social expectations she lives with. For Cherry, looking into the world of the Greasers is a lot like a highly trained horse looking over the fence to where the wild horses roam, thinking the grass looks greener there.

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Though Cherry Valance seems sweet and friendly--and she is--she obviously prefers boys with a dangerous side. Her boyfriend, Bob, is the cruelest and most ruthless of the Socs in the story: He wears a hand full of rings and has previously beaten Johnny severely even before he attacks Ponyboy and tries to drown him in the park. She claims he has a "sweet" side, but it is probably his tough side that attracts her most. She is attracted to Pony and Johnny because Pony is handsome and because Johnny defends her against Dally's unchivalrous behavior. Though Pony and Johnny are young and small, they are greasers and she knows they are tougher than they look. Yet Cherry is still attracted to Dally because she has heard of his reputation, and she tells Pony that she could fall in love with him if she allowed herself to do so.

"I kind of admire him," Cherry said softly...

An attractive cheerleader, Cherry could have her choice of any boy at the high school, but it is the dangerous ones--be they Soc or greaser--that she likes the most.

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