From her point of view, what he was asking could feel very threatening. Notice that when she goes to tell the other waitress, she is not laughing or making fun of him; instead, she looks quite serious and worried--almost scared. Some women feel like they have to be on a high level of alert against danger whenever they are out in public interacting with unknown men, and a waitress sees a lot of men she doesn't know every day.
From Charlie's point of view, he was trying to do a nice thing, but he didn't think about how unfair it is to go to a woman's workplace--a workplace where being nice to him is part of her job--and put her in that awkward and potentially dangerous position. It's a little ironic that as a writer, he is supposed to be able to metaphorically put himself in other people's positions and understand others' thoughts and feelings but in his actual life he failed at a very basic, elementary chance to do that.
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