What were Darry's feelings when he saw Paul Holden in The Outsiders?
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Darry is ashamed when he sees Paul Holden, because he is a reminder of what Darry might have had.
Darry is surprised to see Paul Holden. He used to be on the football team with Darry. He seems to look down on Darry now, making Darry feel embarrassed to be a greaser.
[You] could see he hated Paul now. It wasn't only jealousy— Darry had a right to be jealous; he was ashamed to be on our side, ashamed to be seen with the Brumly boys, Shepard's gang, maybe even us. (ch 9, p. 143)
Darry does not like the expression of contempt, hatred, or pity on Paul’s face. Ponyboy says that only he and Soda can tell what is going on inside Darry’s head as he looks at Paul, and remembers the life he used to have or might have had, if his parents had not died and left him the head of the family for his two brothers.
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