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! – David Jan 14 '11 at 0:17
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locked by RegDwight ΒВBẞ8 Jul 15 '11 at 13:25

16 Answers

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"Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo."

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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
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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 – eventualEntropy 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
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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
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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:

Edədedədədit.

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

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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
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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
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"Ending a sentence with a preposition is something up with which we will not put." --Winston Churchill

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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
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How about some semantic awkwardness?

"Colorless green ideas sleep furiously" —Noam Chomsky

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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 at 23:01
Also: "'Twas brillig, and the slithy toves..." (Jabberwocky) – Hexagon Tiling Mar 19 at 23:03
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In

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.

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"It is what it's"

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It's not grammatically correct to use a positive contraction at the end of a sentence. E.g. we don't say "Yes I'm" or "There he's". – delete Sep 3 '10 at 15:04
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@Neil : The link on the sentence already goes to that question. – JohnFx Sep 3 '10 at 21:28
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@Shinto - You have a citation for that assertion? Nohat came the closest to an explanation of why that would be incorrect, but I am still unconvinced. – JohnFx Sep 3 '10 at 21:32
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I'm a native speaker of English and actually majored in it for two years of college before switching to Comp Sci. At no time did I ever hear than my intuition made something a rule. I suppose by that standard anything I think is right is. So I decree this construct to be proper grammar. – JohnFx Sep 4 '10 at 3:06
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@JohnFx, please see my new answer to the question you link to here. It explains why this is in fact ungrammatical. – nohat Sep 4 '10 at 19:09
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I know this one:

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

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"Amn't I?" grates on my ears...

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It's like building a building.

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My grandfather's favorite is:

What noise annoys an oyster?

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Obviously, a noisy noise annoys an oyster. – TimLymington Jun 23 '11 at 13:46
<*Wah wah waaaaaahh*> Good one! – Mike Christian Jun 23 '11 at 23:01
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If your feet smell and your nose is running, then you might have been built upside down.

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