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A long time back an article was published in a newspaper with the heading "Nehru and Menon". By mistake the spacing between the words was not adequate. Then next day a corrigendum was published by the same newspaper:

"The spacing between Nehru and "and" and "and" and Menon was not adequate."

So a you can see a sentence with "and" repeated 5 times consecutively without grammatical error.

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It's generally going to be a very artificial sentence.

Twice is quite possible, for example: "She said 'and' and he said 'or'."

3: "She had to choose between 'and' and 'and/or."

4: "She had to choose from 'both... and, 'and' and 'and/or'."

5: "She had to choose from the following options: 'both... and' and 'and' and 'and/or'."

There is a well-known riddle along these lines that has as its answer perhaps the least artificial-sounding sentence that could use "and" five times in a row. In it, someone has a sign made that includes the word "and" in it. For instance the sign might read: "Parts and Service." The customer then want to change the sign, and so they tell the sign-makers something like the following: "I need you to put more space between 'Parts' and 'and' and 'and' and 'Service'." It's plausible this sentence could be spoken in real life.

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13y ago
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14y ago

That that that that that teacher used was grammatically correct.

How about 8 times?

I already told you that: that that "that" (that "that" that that teacher used) was grammatically correct.

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11y ago

The pub took delivery of a new sign 'The Horse and Groom'. While it was still waiting to be hung the manager spotted an error. He rang the sign-writer with the information "The gaps between 'Horse' and 'and', and 'and' and 'Groom', are different".

With due acknowledgement to the chap who also provided the Buffaloe buffaloe ... (??) reference and the ... that that that that that ... sentence.

The pub the the Horse and Groom was having its sign replaced. After the work had been done, the manager spotted a mistake. He rand the builders and said " The gaps between horse and and and and and groom are not the same distance"

Read more: What_word_can_be_used_in_one_sentence_five_times_in_a_row_and_still_be_grammatically_correct

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14y ago

You should not write a sentence with the word 'that' repeated 5 timesconsecutively Not only would that be very wordy but it wouldn't make much sense.

I would even stay clear of reusing the word 'that' repetitively throughout multiple sentences because this too will grow tiring and aggravating for the reader.

Take the following example and understand my meaning:

"My brother doesn't like that cat, and that cat doesn't like my brother. That dislike between that cat and my brother doesn't bother me because that cat and my brother like me."

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Q: How can you use and in a sentence five times in a row and still be grammatically correct?
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