7 Simple Sentences That Drive English Speakers Crazy

1. ‘The old man the boat.’

Besides sounding like a rejected Ernest Hemingway title, this deceptive sentence is indeed grammatically correct thanks to some well-placed homonyms—multiple words that share the same spellings but have different meanings. Homonym #1 here is ‘old,’ in this case being used as a noun meaning ‘old people’ (like how you might say, ‘youth is wasted on the young’), not as an adjective modifying ‘man.’Homonym #2, as it happens, is ‘man,’ used here as a verb, meaning ‘to serve in the force of.’ With that in mind, here’s what the sentence is actually saying: ‘The old people serve on the boat.’ May they take this sentence and sail far, far away. (Speaking of homonyms, can you guess the three-letter word that has 645 meanings?)

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