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Dear Daddy-Long-Legs,

I love college and I love you for sending me—I'm very, very happy, and so excited every moment of the time that I can scarcely sleep. You can't imagine how different it is from the John Grier Home. I never dreamed there was such a place in the world. I'm feeling sorry for everybody who isn't a girl and who can't come here; I am sure the college you attended when you were a boy couldn't have been so nice.

This is from Daddy-Long-Legs by Jean Webster. Why did she say such a rude thing "I am sure the college you attended when you were a boy couldn't have been so nice"? Why did she think so, though she doesn't know about him?

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The quoted paragraph shows the protagonist's enthusiasm about her college: she seems to believe (perhaps in an outburst of childish enthusiasm) that it is the best college in the world. As her college is only for girls, and her benefactor is a man, he couldn't have gone there; and if her college is the best in the world, then wherever he went must have been worse. She doesn't mean it in a rude way, as if to put down his education; if anything, it's more sympathetic: she's "feeling sorry for everybody who isn't a girl and who can't come [to her college]", including her benefactor.

This passage is also from very early on in the book and consequently in the protagonist's development. Presumably she doesn't yet have the maturity or social skills required to think that it may be seen as rude to be so dismissive of her benefactor's education.

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