In these days I read 'Dubliners' by James Joyce. There are many difficult expressions I could not make out from dictionaries. Among them, I want to know the meaning of 'fail with'. I've learned of course the word 'fail'-do not succeed basically. But 'fail with' is rather difficult to define. the following sentence is from 'The Dead' of 'Dubliners'.
He would only make himself ridiculous by quoting poetry to them which they could not understand. They would think that he was airing his superior education. He would fail with them just as he had failed with the girl in the pantry. He had taken up a wrong tone. His whole speech was a mistake from first to last, an utter failure.
Not the easiest of writers!
"fail with" = does not succeed with someone [he may be trying to impress them with his charm, or his education, or his poetry, but they are not impressed by it]