Awkward English Sentences That Pass the Grammar Test

2 min read

Anyone who has been inside an English classroom has had to memorize a few grammatical rules: Never end a sentence with a preposition. Never start a sentence with a “with,” “and,” or “but.” Always make sure each sentence has a noun and a verb. As modern English has evolved, sticking to these fundamental rules has sometimes led to awkward or downright confusing sentences. Check out these language fails and see if you can identify what makes them so awkward.

“One morning I shot an elephant in my pajamas. How he got in my pajamas I'll never know.”

This Groucho Marx line has all the elements needed for a grammatically correct sentence, but the structure takes a comedic left turn. A traditional reading of the first sentence assumes Marx was wearing his pajamas when he encountered an elephant. The second sentence reveals funnyman Marx was teasing the reader.

The first line is a garden-path sentence, so named because it leads the reader down the path to the punchline: The elephant is the one wearing the pajamas. Were the pajamas striped or polka-dotted? We may never know.

“I could care less.”

For anyone who reflexively added, “You mean, ‘I couldn’t care less,’” get ready. This phrase is in a grammatical gray area. It brings front and center the battle between prescriptivism and descriptivism. Prescriptivists — or those who believe language is fixed and we should adhere to its rules — insist that “couldn’t” completes the more grammatically correct statement.

Descriptivists, or those who believe language changes based on how speakers use it, have a different opinion. The sentence is grammatically correct because it’s clear to the speaker and the listener what’s intended; we understand that the speaker is out of patience.

“We are some such stuff as dreams are made on.”

While this sentence may not come up in everyday conversation — the dreamy sentiment is from Shakespeare’s The Tempest — it does highlight an element that often divides grammarians: ending a sentence with a preposition.

True, ending a sentence with a preposition makes the sentence less formal, but it’s still grammatically correct as long as an object is not missing from the sentence.

Correct: Which movie theater did you go to?

Incorrect: The bright sign blinked above.

In the second sentence, it’s not clear what the sign is blinking above. The final preposition leaves open more questions than it answers.

“To Boldly Go Where No Man Has Gone Before.”

Star Trek fans, rejoice! This TV catchphrase, uttered at the beginning of every episode, caused quite the kerfuffle when the show aired. Apparently sci-fi fans were just as concerned with terrestrial grammar as they were space exploration.

The adverb “boldly” splits the infinitive “to go.” It’s generally considered a grammatical gaffe, a rule that comes from Latin. But English borrows from multiple languages and — thanks to Noah Webster, among others — changes the spelling and use of different words. While it may be grammatically incorrect in Latin, this phrase is just fine in English.

When we encounter clunky or confusing phrases, many of us reach for our red pens (mental or literal). As these examples show, some of these awkward phrases pass the grammatical test.

Featured image credit: IvelinRadkov/ iStock

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