11 Confusing English Sentences That Will Make You Wish You Spoke Telepathically

(Last Updated On: August 2, 2021)

English is super confusing, and if you’re trying to learn it your brain has probably been broken at least once. If you know English, you probably realize you don’t actually know English every other week, because everything has rules until it doesn’t. But you could probably say this more generally about language as a whole–English is just notoriously difficult as a second language. Anyway, here are some confusing English sentences so nightmarish you’ll wish we all spoke telepathically. 

Further Reading: What Is the Longest Word in English?

Confusing English Sentences

1. A ship-shipping ship ships shipping-ships

Whoever made “ship” a noun, adjective, and a verb should be thrown off the ship. 

But really this just means a boat-shipping boat is moving boats around. 

2. Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

Buffalo is used as a noun (the animal, and the city), as well as a verb meaning “to intimidate.”

Here are three more sentences that are just the same word repeated. All of them exploit the fact that each word can be both a noun and a verb.

Police police Police police police police Police police.

Can-can can-can can can can can can-can.

Will, will Will will Will Will’s will?

3. All the faith he had had had had no effect on the outcome of his life.

Every now and then you probably catch yourself using “had” twice in a row. You know, like “I was told to leave before I had had the chance to say my piece.” This is because you are referring to the past twice. The premise of your sentence takes place in the past, and you’re also referring to a time that occurred in the past relative to that sentence. “Had” is used twice in different contexts because both the past tense and past participle of the infinitive “to have.”

This is a long way of saying the above sentence exploits this twice in a row. 

4. The old man the boats.

This sentence exploits the fact that you probably thought “old” was an adjective describing the man who is on the boat. It’s actually a noun, and “man” is the verb acting on the boat.

Maybe it’s just an old boat?

5. I never said they stole my money.

If it’s a sextillion bill it doesn’t really matter though.

This doesn’t seem confusing until you realize you can emphasize every single word in this sentence and it will dramatically change its meaning. 

Example, emphasize “never” and you mean that you didn’t say your money was stolen. Emphasize “said” and you mean you only implied your money was stolen. Emphasize “I,” and you mean someone else said this sentence instead. 

6. A rough-coated, dough-faced, thoughtful ploughman strode through the streets of Scarborough; after falling into a slough, he coughed and hiccoughed.

This sentence is more of a pronunciation game, exploiting a total of eight different ways the “-ough” sound is pronounced. 

7. The horse raced past the barn fell.

Literally all this sentence needs is a simple “that” to change it to “the horse that was raced past the barn fell.” Yes, this is grammatically correct and often used as the example of the garden-path sentence. What makes it special is probably what you experienced when you first read it. The word “fell” likely made you reread the sentence and re-evaluate the sentence, as “raced” is what most consider the main verb. This is because garden-path sentences break the agent, action, patient order most phrases are evaluated in. 

8. I do not know where family doctors acquired illegibly perplexing handwriting; nevertheless, extraordinary pharmaceutical intellectuality, counterbalancing indecipherability, transcendentalizes intercommunications’ incomprehensibleness.

This sentence isn’t really confusing more than it is neat. Dimitri Borgmann is attributed to it, and it’s a sentence in which each word has exactly one letter more than the one that came before it. 

We still don’t know what’s more confusing. Why doctor handwriting is basically scribbles, or how pharmacists can understand it. 

9. The blind man fell into the well, because he could not see that well.

Do we mean the blind man was not good at seeing, or that he could not see the well he fell into? 

There’s also “I see,” the blind man said, as he picked up the hammer and saw. 


10. Read rhymes with lead, and read rhymes with lead, but read and lead don’t rhyme, and neither do read and lead.

Like the “-ough” sentence, this one exploits the different ways in which “-ead” can be pronounced. 

11. If it is it, it is it; if it is it is it, it is.

Break it down and this sentence is just comparing three objects and means the following.

If X is Y, then Y is Z; if you are trying to make the point that this means X is therefore Z by proxy, then your argument is correct. 

Is English confusing?

It is. 



About Kyler 704 Articles
Kyler is a content writer at Sporcle living in Seattle, and is currently studying at the University of Washington School of Law. He's been writing for Sporcle since 2019; sometimes the blog is an excellent platform to answer random personal questions he has about the world. Most of his free time is spent drinking black coffee like water.