John while Mary had had had had had had had had had was correct

A grade school-level puzzle in grammar and syntax. One must correctly insert punctuation and capitalization to yield grammatically correct English, to whit:

John, while Mary had had "had had," had had "had." "Had had" was correct.

Alternatively, one can replace the period with a semicolon.
that that is is that that is not is not that is it is it not

A grade-school grammar puzzle, I first encountered this in Flowers for Algernon. Correctly punctuated:

"That that is, is. That that is not, is not. That is it, is it not?"

A similar puzzle was once presented to me: Come up with a paragraph with 5 'and's in a row, which is syntactically correct.

The answer:

Once upon a time, there was a man who owned a pub, called 'The Dog and Duck'. He wanted a nice new sign to hang outside his pub, so he want to a sign maker, and asked for a sign saying 'The Dog and Duck'.

A week went by, and the sign maker returned with the sign. It read 'The Dogandduck'. 'No,' said the pub owner. 'That's all wrong. You've missed out the spaces!'.

'What spaces?' asked the sign maker.

'The spaces', said the pub owner, 'between 'Dog' and 'and', and 'and' and Duck'

The solutions to these puzzles have always bothered me. They rely on using a word in the sense of describing that particular word, rather than its usual sense.

For example, if I talk about a sign reading "Dog and Duck", I can say it contains the word 'dog', and the word 'duck'. I'm not actually talking about a dog or a duck - I'm talking about the words, which are really just symbols in this context.

So in order to solve the puzzle "Create a sentence containing five consecutive 'and's", I might just as well come up with something like the following:

An unusually inept signwriter accidentally erected a sign reading "and and and and and".

Doesn't sound as clever as the more traditional solution, but it's just as valid. Or invalid.

Actually, I remember this puzzle from books of yesteryear with an extra two had's.

smith where jones had had had had had had had had had had had the examiners approval

becomes

Smith, where Jones had had "had had", had had "had". "Had had" had had the examiners approval.

That is a quite ridiculous ELEVEN had's in a row!

oysters oysters oysters eat eat eat

Basically, there are these oysters who eat other oysters, and these bigger oysters who eat the oyster-eating oysters, but even the tiny oysters at the bottom of the food chain, they still have to eat.

This was presented to me in a linguistics class (Syntax, with Steven Weisler) at Hampshire college, as an example of how an apparently nonsensical string of words can be parsed into a valid sentence. It's in the same vein as "John while Mary had had had had had had had had had was correct", but more like "Buffalo buffalo buffalo Buffalo buffalo" in that it seems to me to be free of the objectionable "quoting" problem about which TenMinJoe complains.

Disclaimer: this is the only linguistics class I ever took. I don't know linguistics terminology.

Presumably whoever came up with this example saw it on a roadside advertisement or something: "Oysters! Oysters! Oysters! Eat! Eat! Eat! But if you take it as a sentence, "Oysters oysters oysters eat eat eat," with some struggle you can make sense of it. I think I may have seen this in another linguistics textbook with something other than oysters.

OYSTERS EAT Any native speaker should be able to understand "Oysters eat." There are oysters in the ocean, and in order to stay alive they eat stuff. But suppose there are other, bigger oysters, and they actually eat other oysters:

OYSTERS OYSTERS EAT EAT. "The oysters that the (oyster-eating) oysters eat, also eat." These oyster-eating oysters, you see, eat oysters who do themselves eat. The original (non-cannibal) oysters are still the subject of the sentence, and all they are doing is eating. They have just been described as those oysters whom these new cannibal oysters eat. That's a reasonable step to take. For some reason, some people have trouble with the third step, where we learn that these oyster-eating oysters are themselves eaten by still more cannibalistic oysters who feed on oyster-eating-osyters -- "oyster-eating-oyster-eating oysters", [a hyphenation dilemma if there ever was one]:

OYSTERS OYSTERS OYSTERS EAT EAT EAT. "[The simple] oysters [that the oyster-eating] oysters eat, [which in turn oyster-eating-oyster-eating] oysters eat, [these simple oysters also have to] eat. "These oysters, who are eaten by oyster-eating-oysters, who are in turn eaten by oyster-eating-oyster-eating oysters, they eat." Oysters [whom] oysters oysters eat eat, [also] eat. The original non-cannibal oysters are still the subject of the sentence, but their predators are also being described, by describing their own predators.

We are confusing here two slightly different, yet related puzzles. The first is "given word string s, parse it correctly" (the "had had" puzzles) while the second is the seemingly harder "generate a word string conforming to an unusual constraint that satisfies the rules of grammar" (the "and and" puzzles).

Obviously, TenMinJoe provides an excellent (IMHO) 'solution', that is perfectly valid. However, it would be marked wrong in an exam - why? Presumably, because it follows the letter and not the spirit of the test. However, even the first ("had had") puzzles have potential solutions that could be considered 'invalid'. Consider:

John, while Mary had had "had," had had "had had." "Had had" was correct.

To save you straining your eyes, this is simply a symmetry reversal* of the situation. Possibly a politically incorrect one, since it is now Mary who is wrong! :) In any case, it is clear that there are several possible solutions - there is no unambiguous way of parsing the sentence. Just as with those annoying "series completion" tests you get in IQ tests, a purely mechanical approach to determining the 'correct' answer is doomed to faliure.
*I'm currently distracting myself from combinatorial graph generation, which is why this looked obvious to me! :)
The most challenging one of these I ever found was to do with onions. What I like about it is that whilst it is contrived - these always are - it passes TenMinJoe's test. The task was set me upon hearing someone leaving my train saying 'You know, the onions onions onions one?'. Possibly the most frustrating conversational snippet ever. Obviously, I'd have to construct this sentence. Sleep nor food would be my solace until this was my defeated foe.

Obviously, I could have copped out. It would have been easy to have a couple both of whom were called Onions, who exclaim each other's names. It would have been easier to have a vegtable seller, declaiming his goods. Obviously, speech and proper nouns offer easy but ultimately unsatisfying recourse. Like cheating in Civ2. What I wanted was to find a sentence which made grammatical sense. Perhaps actual sense would be A Bridge too Far. I'd settle for some Colourless green ideas sleep furiously situation. It don't even occur to me that this could have been some -gry type puzzle. Credulous fool that I am.

I started with a simple sentence:
I bought some onions.
This was easy, I thought. I'm a third done already. This is great. Next step was obvious. Contrived, but evident.
I bought some, having called them onions, onions.
So there's two. Phew, I thought, I can do this. Ok, so I lied. I could have had 'seen his' over 'called them', but I prefered the silliness. Then I stalled. I could find no feasible way whatsoever to incorporate a further non-ejaculatory part of speech into the sentence. Damn that man!

Then, weeks later, trawling through C Literature from about 1880, I came across the phrase 'to know one's onions', apparently used to signify considerable familiarity with a topic. So. I was all set.

Incorporating my new friend was not difficult. The sense of the sentence is that, since I am such an expert on the things, I identified some objects as onions, and then bought them. The sentence in full runs like this:
I bought some, having called them -knowing my onions- onions, onions.
Oh yes. And now we can all get some rest.

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