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Are these two sentences correct according to English grammar?

  • Which story was longer?

  • Which story was the longest?

One of my colleagues said that the first question is wrong according to English.

  • I'm guessing your colleague isn't a native speaker. Both versions (and also Which story was longest?, with no article) are common, and mean the same. But I would guess the fourth permutation (Which story was the longer?) has become far less common over the past century or two (it's still perfectly grammatical, though). – FumbleFingers Feb 11 '16 at 14:55
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If you are talking about more than two stories, your colleague, I think, is right. You should use the superlative longest for more than two stories as follows:

Which story was the longest?

However, if you are talking about comparison between two stories, your colleague isn't right. You can use either the comparative longer or the superlative longest. So both the following sentences are correct:

Which story is (the) longer?

Which story is the longest?

You usually use the superlative with "the". But sometimes you use it without " the".

Besides, the use of the superlative for two things or persons is more common in informal English.

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    The use of the comparative with "the" and without a noun or pronoun, for example, "Which is the longer?" is somewhat formal, but the comparative is used in conversation every day and there's nothing formal about it. You take the bigger piece of cake. I'm on a diet. --Which one is bigger? They both look the same size to me. – Tᴚoɯɐuo Feb 11 '16 at 17:23

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