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This is a cool riddle, which my Maths teacher taught our class, 25 years ago. I still remember it and find it very cool.

Can you create a perfectly valid English sentence, which makes perfect sense, but which contains the word "and" in it, five times consecutively in a row ?

"Something-or-other and and and and and something-else."

Let's see if anyone else knows the answer to this one.

I'll post the answer in a couple of days.

(Dedicated to Mr Quick, my excellent Maths teacher from Tavistock College, Devon, England.)

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    $\begingroup$ There's a similar puzzle that requires you to punctuate eleven "had"s in a row. $\endgroup$
    – paste
    Commented May 2, 2016 at 13:37
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    $\begingroup$ Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo. $\endgroup$
    – Dave
    Commented May 2, 2016 at 14:07
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    $\begingroup$ Also one with "that": puzzling.stackexchange.com/questions/2578 $\endgroup$
    – f''
    Commented May 2, 2016 at 18:35
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    $\begingroup$ All of the knowledge he had had had had no impact on his ability to answer riddles $\endgroup$
    – Ashl
    Commented May 2, 2016 at 19:52
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    $\begingroup$ I learnt a similar one in Spanish: ¿Cómo como? Como como como. $\endgroup$
    – Manuel
    Commented May 3, 2016 at 3:07

2 Answers 2

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I've also heard it before :)

Let's say we have a store owner and his clerk. The store owner want the clerk to make a sign for the shop, which has the name (for example): "Toys And Puzzles".

So, the clerk makes the sign and presents it to the owner.
The owner thinks the spacing isn't really good. It currently looks something like:
Toys And Puzzles
but he wanted it to look more like:
Toys And Puzzles

So he says to the clerk:
"The spacing between Toys and And and And and Puzzles should be a bit larger. Could you please fix that?"

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    $\begingroup$ The funny thing about this is that despite how awkward that looks in text form, when you say it out aloud it's not that bad. $\endgroup$
    – Xylius
    Commented May 2, 2016 at 11:30
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    $\begingroup$ Just five ands? Amateur ;-) $\endgroup$
    – Angew is no longer proud of SO
    Commented May 2, 2016 at 11:46
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    $\begingroup$ @Angew: Wikipedia gives an example with forty-six "and"s in a row. (The last entry under "Lexical ambiguity". $\endgroup$
    – Darrel Hoffman
    Commented May 2, 2016 at 13:41
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    $\begingroup$ I find the spacing in this answer to be a little tight. Could you add more space between toys and and and and and and and and and and and and and puzzles? $\endgroup$
    – Ian MacDonald
    Commented May 2, 2016 at 14:33
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    $\begingroup$ 'and' has lost all meaning to me... $\endgroup$
    – G_as_in_Gnome
    Commented Mar 31, 2017 at 7:23
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The question itself provides an answer:

Can you create a perfectly valid English sentence, which makes perfect sense, but which contains the word "and" in it, five times consecutively in a row, like this: "Something-or-other and and and and and something-else."?

I kept it relatively intact but we could easily alter it slightly so that it only contains valid words.

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