What are some examples of awkward sounding but grammatically correct sentences?

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    For grammarians who don't want to strand prepositions, shouldn't the best sentence construction be: "About whom is this story?" :) – Kosmonaut Sep 3 '10 at 13:21
  • I haven't had this much fun with English since I don't know when. Thank you! – Mei Jan 14 '11 at 0:17

15 Answers 15


"Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo."

  • 3
    That is truly a bizarre sentence. – JohnFx Sep 3 '10 at 15:03
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    It means "blue text means it's a link you should click on" – Seamus Sep 7 '10 at 14:01
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    Rather: Bison from the city of Buffalo which are intimidated by other bison from the city of Buffalo themselves intimidate other bison from the city of Buffalo. – Doug Oct 15 '10 at 16:49
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    @Seamus I see red text – Midhat Nov 28 '10 at 7:28
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    @Midhat - I think that means you are in the matrix – mgb Mar 29 '11 at 23:02

That that exists exists in that that that that exists exists in.

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    Nice — unlike the had-had sentence, this doesn't require any additional punctuation! – ShreevatsaR Sep 9 '10 at 7:37
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    I can't wrap my head around this one – Steve Vermeulen Sep 9 '10 at 13:20
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    Brackets may help: (That that exists) exists in (that that (that that exists) exists in). [Or rewriting it, letting X stand for "that that exists": X exists in that that X exists in. X exists in whatever X exists in. X exists where it does.] – ShreevatsaR Sep 10 '10 at 11:41
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    @ShreevatsaR: LISP-like English ftw! – R. Martinho Fernandes Oct 13 '10 at 9:14

Jim opens a cafe selling fish and chips. He has a sign made. It arrives and it says "fishandchips". So he rings up the sign company and says:

You need to put more space between "fish" and "and" and "and" and "chips"
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    Or rather, he writes the company and says “You need to put more space between fish and and and and and chips” and they write back, saying “in your request, you need to put quotation marks between ‘fish’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘and’ and ‘chips’”. – nohat Sep 7 '10 at 16:50
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    And he writes back saying... oh never mind... – Seamus Sep 7 '10 at 17:19
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    @nohat I didn't know that one, thanks! – Jürgen A. Erhard Jan 13 '11 at 23:56

James while John had had had had had had had had had had had a better effect on the teacher.

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    If you accept Had as a boy’s name... “In the English test, while Alice had had ‘had had’, Had had had ‘had’; had Had had ‘had had’, Had would have been correct. – Timwi Sep 9 '10 at 1:26

As far as awkward-sounding is concerned, I submit there are few sentences spoken in English that sound more awkward than:

Ed had edited it.

This is very hard to say in the rapid flow of conversation, and results in a sound something like:


Try it for yourself, speaking quickly, and you'll see what I mean.

  • 7
    A friend showed me a similar one, "Jiggle it a little, it'll open." – Tesserex Jun 20 '11 at 19:37
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    This reminds me of a (slightly dirty) joke: How do you titillate an ocelot? Oscillate its tit a lot. – MT_Head Jun 21 '11 at 5:55
  • @Tesserex I like that! In Yorkshire, how do people say "It is not in the tin"? - Tin tin tin. – Mynamite Jan 27 '13 at 2:41

Ending a sentence with a preposition is something up with which we will not put.
Someone who was not Winston Churchill

  • If you're going to attribute it to Churchill, please get the quotation right. – moioci Sep 3 '10 at 22:42
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    @moioci--If you're going to point out an error, please provide evidence that it's incorrect. I found this link: wsu.edu/~brians/errors/churchill.html – kajaco Sep 4 '10 at 14:16
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    Even though the quotation is apocryphal, the version you quoted is listed under "so scrambled it comes out backward" — the usual story has Churchill complaining about pedants insisting on not ending sentences with a preposition (and deliberately and ironically over-applying their rule), while your version has Churchill recommending the rule himself. – ShreevatsaR Sep 9 '10 at 7:35
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    Oh BTW, I don't think this counts as a grammatically correct sentence; it's not grammatical to split "put up" like that. – ShreevatsaR Sep 9 '10 at 7:36
  • This wasn't Churchill anyway. That's a misattribution no longer to be put up with. – RegDwigнt Oct 10 '12 at 10:26


I found John in an unenviable position.

there are the syllables "an", "en", "in", "on", "un" (i.e. all of "aeiou") run together. This makes it a little tricky to say.


How about some semantic awkwardness?

"Colorless green ideas sleep furiously" —Noam Chomsky

  • 8
    For grammatically correct meaningless sentences, I prefer Stephen Fry's sentence in his lovely "Language" sketch: "Hold the newsreader's nose squarely, waiter, or friendly milk will countermand my trousers." – ShreevatsaR Sep 9 '10 at 7:42
  • There is also the famous nonsense paragraph about "no soap" here: jstor.org/discover/10.2307/… – Hexagon Tiling Mar 19 '12 at 23:01
  • Also: "'Twas brillig, and the slithy toves..." (Jabberwocky) – Hexagon Tiling Mar 19 '12 at 23:03

"The horse raced past the barn fell."

  • My favorite example of sentences that seem difficult to parse – livresque Feb 6 '13 at 15:32

My grandfather's favorite is:

What noise annoys an oyster?

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    Obviously, a noisy noise annoys an oyster. – Tim Lymington Jun 23 '11 at 13:46
  • <*Wah wah waaaaaahh*> Good one! – Mike Christian Jun 23 '11 at 23:01
  • Nose knows no snows. – endolith Mar 12 '15 at 2:48

The article you linked has a few other examples of such sentences. As it says, "Any word that is both an animate plural noun and a transitive verb will work."


Try this one. Who polices the police? Police police police police. Who polices the police police? Police police police police police police. Etc.


You'll probably want to put some punctuation in these:

  • Wouldn't the sentence "I want to put a hyphen between the words Fish and and and and and Chips in my 'Fish and Chips' sign" have been clearer if quotation marks had been placed before Fish, and between Fish and and, and and and and, and and and and, and and and and, and and and and, and and and Chips, as well as after Chips?

  • James while John had had had had had had had had had had had a better effect on the teacher.


I know this one:

Time times time times time squared equals time times time times time times time


That that is is that that is not is not is that it it is

  • This is not grammatical, as it is missing punctuation. – John Gietzen Jun 28 '12 at 3:47

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