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I believe you have confused Dally with Darry in the second part of your post, but here goes.
Dally comes on to Cherry the only way he knows how--tough, crude and sarcastic. He talks dirty to her, and Cherry eventually throws a soda in his face. However, we find out later that Cherry is actually taken with Dallas Winston, and she says that she could fall in love with him if she saw him again. She likes dangerous types, since her boyfriend is the violent yet handsome Soc, Bob Sheldon. So, though the two never get together, Dally's approach works on Cherry. Needless to say, Dally likes Cherry's spirit and good looks, but he knows better about mixing with a Soc.
Ponyboy is younger and shyer, so he talks to both girls as he would schoolmates. He never forgets that he's a greaser, but he feels important when the girls tell him they feel safe around him. The girls think Pony is cute--and his brother, Sodapop, even cuter--and Cherry decides that she can talk to him about anything. Pony feels the same way about Cherry, and she stands up for Ponyboy later in court. He considers her a friend, though they go back to their own greaser and Soc worlds at the end of the novel.
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