I think his problem with the situation is that she essentially told him that he has to give more for the same outcome that other guys would get for free. That is probably what he heard from that conversation.
Thats what he heard because thats what she said. Why would a woman even be comfortable saying something like that if they didnt mean it to some extent. And thing is she's not confused because she doesnt think she meant it that way (because she did), she's confused because she, as a woman; doesnt see whats wrong with being in the streets and then settling for a dude; ALOT of women see nothing wrong with that.
EDIT : To answer the bolded, they were drinking. Thats why she was comfortable.
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