In Search of the Perfect Garden Path Sentence

Making sense (and nonsense) out of the world’s most devious sentences.

Jack Shepherd
Cellar Door

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Happy England, by Helen Allingham (Via British Museum)

The best garden path sentences rely on one of two tricks to garden-path¹ you: 1) Noun/verb ambiguity. And 2) Unmarked relative clauses.

It’s all terribly devious, but with just these two devices, you can throw an unsuspecting sentence-reader into a sea of madness and confusion, leaving them sprawling in terror and disbelief as the sentence they thought they were reading careens right over the edge of a cliff. My favorite garden path sentence does this in just five words:

The old man the boat.

“What on earth …” (says our befuddled sentence-reader, spitting out a cheroot as a monocle ejects itself forcefully from their eye socket) “… is this terrible old man ‘the boating,’ and how does any man, young or old, ‘the boat’ in the first place?” The answer, of course, is that he doesn’t—the only thing anyone is doing in this famous garden path sentence is “manning,” and it’s the old who are doing it to the boat. This is a classic case of noun/verb ambiguity (one does not expect “man” as a verb, especially when it follows “old”), and it’s devastatingly effective.

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Jack Shepherd
Cellar Door

I have a newsletter about crossword puzzles and a podcast about rom-coms. Formerly editorial director @BuzzFeed. Email: JackAShepherd at gmail